Islamorada

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$275

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Islamorada “The Getaway” Relax in Florida Keys!

Islamorada house
3 BR / 2 BA / Sleeps 6 | Quick view
Excellent3 Reviews

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Reviews

(3)

Thank you for considering Our home in the Florida Keys!... Our slice of Paradise! Stay at a Luxury Townhome at Executive Bay Club (Islamorada , Florida ) The Executive Bay Club is located in Islamorada which is best known for it's crystal blue water where you can enjoy sport fishing, snorkeling, diving and boating…
  • Waterfront
  • Wireless Internet
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Suitable for children
  • Suitable for the elderly - ask

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(3)

The Keys at its Best

Left on Mar 26, 2014 for a stay in March 2014

We stayed at "The Getaway" for spring break...a break from it all. This is place was wonderful! First, Luis and Paula were wonderful from initial inquiries, to providing suggestions for things to do and places to go, through the end of our stay and follow up. They were available by phone and email if we had a question. The home was wonderfully decorated and clean! two sets of bunk beds and a…

$258

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Florida Keys Beautiful 2B 2B Townhouse

Islamorada villa
2 BR / 2 BA / Sleeps 6 | Quick view
Excellent4 Reviews

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Reviews

(4)

Vacation in Paradise!!... you will love this fun filled, relaxing townhouse in the beautiful Florida Keys. The Executive Bay Club is located in Islamorada, the Sport Fishing Capital of the World. It is a private, gated community and the grounds have 2 tennis courts, a swimming pool, a clubhouse, a private beach and a …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Central heating
  • Suitable for children

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(4)

Marvelous Property- First Class All the Way!

Left on Jan 16, 2015 for a stay in December 2014

The Daniels' property was an outstanding vacation rental. It is centrally located in the middle of Islamorada. This is a two story end unit condo that is in perfect, (yes, perfect) condition. There is a roomy master bedroom, 2nd bedroom and a loft (accessible through the master). The living room is expansive, the kitchen is modern, ultra well equipped and easy to use.

I would love …

$125

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Serenity Waterfront-Dock, View, Tiki Hut, spa/hot

Islamorada villa
1 BR / 1 BA / Sleeps 3 | Quick view
Excellent7 Reviews

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Reviews

(7)

Located in beautiful Plantation Key, the first Island of Islamorada. An area of all waterfront homes Wifi, boat dock, trailer parking, and all amenities are included also, Lovely Tiki Hut overlooking the water. Plus a huge covered entertainment area complete with dining areas, settee and gas BBQ. Dockage for …
  • Waterfront
  • Hot Tub/Jacuzzi
  • Internet Access
  • Outdoor Dining Area
  • A/C or climate control
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

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Reviews

(7)

Great owners-average accommodations

Left on Apr 25, 2014 for a stay in April 2014

You've got to like Key Islamarada because it's strictly for boaters and this place has a slip for yours. We booked it because it was one of the few rentals with handicapped access. You will spend most of your time in the covered recreation area, which is a large shaded area and always had a nice breeze while we were there. Some things in the unit could use owner's attention, such as the glued …

$243

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Islamorada PARADISE FOUND 3 bedroom/2 bath

Islamorada townhouse
3 BR / 2 BA / Sleeps 6 | Quick view
Excellent3 Reviews

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Reviews

(3)

BEAUTIFUL NEWLY REMODELED 3 BEDROOM, 2 FULL BATHROOM VACATION RENTAL IS LOCATED IN THE EXECUTIVE BAY CLUB. BREATHTAKING BAY VIEW FROM YOUR OWN BACK YARD! UNIT HAS BRAND NEW CUTOME KITCHEN CABINETS WITH GRANITE COUNTER TOPS. ALL STAINLESS STEEL APPLIANCES, DOUBLE DOOR REFRIGERATOR, DISHWASHER, GLASS STOVE COUNTER …
  • Ocean or water views
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Suitable for children

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(3)

Beautiful, relaxing and comfortable!

Left on Feb 23, 2015 for a stay in December 2014

When we first contacted the owner regarding the rental, she responded immediately and was very nice and helpful. The unit was impeccable when we arrived and the location in the complex was excellent! We were right in front of the pool, and the beach area was very close. One of my favorite things to do during our stay was to sit out in the terrace of the unit and relax while looking at the ocean. …

$400

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You will never want to leave

Matecumbe Key house
3 BR / 3 BA / Sleeps 5 | Quick view
Excellent6 Reviews

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Reviews

(6)

3 bedroom, 2.5 bath home at the end of a quiet private road in Islamorada. Queen bed in the master with a fantastic view of the ocean from your pillow. Two queen beds in the second bedroom with en suite bath The third bedroom is used as an office. From the moment you open the front door you have a view of the ocean …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Pet friendly - ask
  • Suitable for the elderly - ask

Details

Reviews

(6)

Really Super great place. Have stayed here twice and this place

Left on Dec 09, 2013 for a stay in December 2013

We have stayed here twice. Could not ask for a more peaceful and scenic view. Super great place and all of the things that you need. Very clean and very nice. Beautiful inside and out and the owners as nice as the place. Fantastic restaurants within a few miles north or south. One of the nicest little Bass Pro Shops around just a few miles up the road. The sunsets are amazing the mornings are …

$600

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Latitude

Islamorada house
4 BR / 3 BA / Sleeps 8 | Quick view
Excellent1 Reviews

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Reviews

(1)

****This house cannot rent for less than 28 days, per County Ordinance**** Latitude: Freedom of thought or action. No word could better described this Keys Vacation Home. Embrace the serenity of the azure Atlantic Ocean while you relax in the private heated pool. Latitude boasts 2 master suits and two guest rooms. …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Suitable for children
  • Suitable for the elderly

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Reviews

(1)

A wonderful week with extended family

Left on Jun 16, 2013 for a stay in June 2013

Our extended family of 8 had a wonderful week at Latitude. The house is modern and immaculate. There was plenty of space and privacy for everyone. We had a great time watching a huge variety of sealife from the dock. We saw nurse and bonnet-head sharks, crabs, puffer fish, a turtle, stingrays and much more. The house was convenient to several very good restaurants (Pierre's, Islamorada Fish …

$465

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OCEANFRONT pool30'DockGatedPrivate7niteMin6ppl max

Islamorada house
3 BR / 3 BA / Sleeps 6 | Quick view
Excellent6 Reviews

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Reviews

(6)

FOR ADDITIONAL REVIEWS GO TO "HOMEAWAY.COM" LISTING #341722 TO AVOID SCAM WE URGE YOU TO PLEASE CONTACT OWNER BY PHONE BEFORE FINALIZING ANY ARRANGEMENTS IF YOU GET A RESPONSE FROM BESTHOLIDAYRENTALS.COM **** IGNORE IT **** SCAM MINIMUM STAY 7 NIGHTS, MAXIMUM OCCUPANCY 6 PPL, RENTAL PATTERN SATURDAY TO SATURDAY…
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Suitable for children

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(6)

Paradise found

Left on Nov 13, 2012 for a stay in July 2012

Paradisepointe was really everything we hoped for! The views were incredible and we really enjoyed the pool. The grounds and the house were clean and we had everything that we needed to enjoy ourselves. The charcoal and gas grills came in handy since we grilled out during our stay.We really enjoyed the dock for our boat and the easy access to the ocean. We did a lot of boat riding and fishing and…

$170

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Sol Y Mar - 50 Ft. On The Water

Islamorada house
3 BR / 2 BA / Sleeps 4 | Quick view
Excellent1 Reviews

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Reviews

(1)

Welcome to Sol Y Mar SOL Y MAR is 2,500Sq.Ft. of Living Space,Three (3) Bedrooms, Two (2) Bathrooms on Three (3) Levels. Property is located in Tavernier, in Islamorada, Florida (MM90). The Center of the Keys, 1.5 Hours to Miami, 1.5 Hours to Key West; Shopping, Restaurants, Theaters, Sunset Cruises, Diving, and …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Suitable for children - ask
  • Suitable for the elderly - ask

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Reviews

(1)

Near perfection

Left on Apr 25, 2015 for a stay in April 2015

Our family of 5 adults spent a week at Sol Y Mar in Tavernier Florida. We were fortunate to have Nestor Loredo as our agent. The house was all as promised. Nestor met us the and went through everything about the house and provided us with a great deal of information on local attractions. If you are even just thinking of going to the Keys do yourself a GREAT favor and contact Nestor.Our family …

$200

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Islamorada Waterfront Paradise Getaway

Islamorada house
1 BA / Sleeps 2 | Quick view
Excellent26 Reviews

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(26)

PLEASE DO NOT TRY TO BOOK THROUGH FLIPKEY! Booking instructions will be provided when you send your inquiry, saving you a significant amount in FlipKey booking fees. We do not use the optional calendar feature on this listing. Save $700 and book June 27 - July 4 for only $1000 plus tax! This is a very popular rental…
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Suitable for the elderly

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(26)

Great Keys Get away

Left on May 30, 2012 for a stay in April 2012

I have to say everything is as advertised. In fact it looks a lot better in person than the pictures. The room itself is great for two people and has everything you will need. It is a great location to explore the keys. It is very relaxing and quiet. We loved the tiki hut. We spent several hours each day relaxing and reading in the hut. Peter and Ewa are the perfect host. The weather was great …

$400

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Oasis (28 Day Minimum Only)

Islamorada house
3 BR / 3 BA / Sleeps 8 | Quick view
Excellent1 Reviews

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Reviews

(1)

****This house cannot rent for less than 28 days, per County Ordinance**** Ahhhh...Ocean Front...Pool...Dockage...It's all hear at Oasis. Oasis is located at Mile Marker 75.6, in beautiful Islamorada. This Beautiful three bedroom, three bath home will sleep 8 people very Comfortably. Besides the bedrooms there are …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly

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Reviews

(1)

Perfect Honeymoon

Left on May 02, 2012 for a stay in September 2011

Me & my Husband stayed here for our Honeymoon in Sept. 2011. We love the "get away from it all" feel, and this place delivered. When we arrived the very first day, we found a pretty decent size conch shell washed up on shore. Guess the tenant decided to move out, so we kept it. Every morning we woke to the ocean through the glass walls of the master bedroom. We walked the shore every morning…

$1,186

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Southern Diversion Islamorada Great Wedding Venue just renovated

Islamorada house
5 BR / 4 BA / Sleeps 16 | Quick view
Excellent6 Reviews

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Reviews

(6)

This is an exclusive oceanfront private gated estate home with 200 feet of oceanfront on two acres. This property also features 200 feet of dock, Boat lift, Tiki hut on private beach, Heated pool and Wireless remote Internet. Southern Diversion has just been completely renovated. Brand new kitchen including granite …
  • Ocean or water views
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(6)

Perfect location - with space to play both on land and on the water!

Left on Mar 06, 2013 for a stay in February 2013

We just returned from a week in Islamorada at the Southern Diversion estate. The property was just beautiful - from the tree lined drive up to the front of the home to the postcard-like views of the ocean out back. The house had plenty of room for all our extended family, including a bunch of young kiddos. The bunk room was perfect for all the cousins to sleep in. The four bathrooms were great, …

$140

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Seagulls Condominiums, Enjoy the Florida Keys!

Islamorada apartment
1 BR / 1 BA / Sleeps 4 | Quick view
Very Good2 Reviews

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Reviews

(2)

Come enjoy our home away from home. Perfect for a couples retreat. Enjoy your own fully equipped condo. Sip coffee on the balcony and watch the beautiful sunrise. Read one of our Jimmy Buffett books and dream of running away for a life on sea. Once this salt air gets in you you will never want to go home. The …
  • Waterfront
  • Sauna
  • Wireless Internet
  • A/C or climate control
  • Central heating

    Details

    Reviews

    (2)

    Nice unit for the price

    Left on Apr 11, 2015 for a stay in April 2015

    I spent a week at Sea Gulls with my 18 year old daughter. The unit was well equipped and clean. The pool and tennis courts were nice. The view was adequate. To the left, a beautiful view of the ocean, but to the right the high school football field (although the track was accessible and we used daily). We were disappointed in the beach on the property though as it contains no sand. It was a…

    1 / 4

    $229

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    Casa Thorn Moroccan Room

    Islamorada B&B
    1 BR / 1 BA / Sleeps 2 | Quick view

    Details

    The Moroccan room is a fabulous honeymoon destination with king size canopy bed. Room features a/c, coffee maker, heat, microwave, refrigerator, TV, WiFi. Enormous bathroom with sunken tub and terrycloth robes to lounge in includes full breakfast. LOCATED IN A QUIET, SECLUDED, TROPICAL SETTING YET MINUTES TO …
    • Shared outdoor pool (unheated)
    • Hot Tub/Jacuzzi
    • Internet Access
    • Housekeeping Optional
    • Outdoor Dining Area
    • Pet friendly
    • Smoking allowed - ask
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask
    1 / 5

    $179

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    Casa Thorn Poolside Malaysian Room

    Islamorada B&B
    1 BR / 1 BA / Sleeps 3 | Quick view

    Details

    Malaysian room is poolside in a tropical atmosphere facing a beautiful waterfall. Features a mini kitchen with blender, coffee maker, microwave, refrigerator and toaster oven. A/C, heat, TV and WiFi. Includes a full breakfast. LOCATED IN A QUIET, SECLUDED, TROPICAL SETTING YET MINUTES TO FISHING, DIVING, …
    • Wireless Internet
    • A/C or climate control
    • Central heating
    • Patio
    • Garden
    • Pet friendly
    • Smoking allowed - ask
    • Suitable for children
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask
    1 / 24

    $279

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    LUXURY KEYS HOME IN PARADISE-106 ANGLERS REEF

    Islamorada villa
    2 BR / 3 BA / Sleeps 6 | Quick view

    Details

    This beautiful villa has all new furnishings and is located in the exclusive oceanfront gated community of Angler's Reef in Islamorada at Mile Marker 84. Angler's reef is a luxury retreat resort framed by mangroves and the clear waters of the Atlantic ocean with 52 colonial detached villas set along quaint streets …
    • Waterfront
    • Ocean or water views
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Suitable for children
    • Suitable for the elderly
    1 / 25

    $243

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    Anglers Reef Islamorada Florida Sleeps 6

    Islamorada house
    2 BR / 3 BA / Sleeps 6 | Quick view

    Details

    2 bedrooms, 2 full bathrooms, 1 half bathroom, sleeps 6 This magnificent oceanfront home is at Mile Marker 85 in exclusive Angler's Reef - 52 homes . Quaint streets & walking paths wind through this village-styled retreat. Enjoy a drink in the lushly landscaped pool area overlooking the ocean or on the 500' of …
    • Waterfront
    • Ocean or water views
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Pet friendly - ask
    • Suitable for children
    • Suitable for the elderly

    $180

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    Islamorada Waterfront Paradise 1

    Matecumbe Key studio
    1 BR / 1 BA / Sleeps 2 | Quick view
    Excellent7 Reviews

    Details

    Reviews

    (7)

    This is a very popular rental, so book your preferred week well in advance of peak season! I reply to EVERY inquiry. If you do not receive a reply, please contact me again! Email me for additional pictures of this wonderful hideaway. EVERY RENTER IS PROVIDED WITH A COMPLIMENTARY BOTTLE OF WINE. Dive right into …
    • Waterfront
    • Ocean or water views
    • Wireless Internet
    • Outdoor Dining Area
    • A/C or climate control
    • Suitable for children - ask

    Details

    Reviews

    (7)

    Great vacation location

    Left on Mar 03, 2014 for a stay in February 2014

    We had a lovely time staying here. The highlights were the large back yard on the water with the chiki hut and the many other places to relax on the dock. And we even saw a manatee! Having the bicycles to explore the neighborhood and the double kayak to get out on the water was a bonus. The room itself was spotless and very well set up. And fishing off the dock was so much fun! Loved having the …

    $200

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    Beautiful Captain's Cove

    Islamorada villa
    3 BR / 2 BA / Sleeps 8 | Quick view
    Excellent1 Reviews

    Details

    Reviews

    (1)

    Relax and enjoy a peaceful getaway in beautiful Islamorada, Florida. This unique home is nestled on a bay overlooking the ocean. We are located on Lower Matecumbe Key just a few miles south of the hustle and bustle of downtown Islamorada. This is a spacious three bedroom with vaulted ceilings, a loft in the master …
    • Waterfront
    • Ocean or water views
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Pet friendly - ask
    • Suitable for children
    • Suitable for the elderly - ask

    Details

    Reviews

    (1)

    Great property!

    Left on Nov 18, 2014 for a stay in November 2014

    We stayed at Captains Cove again for our annual fishing weekend. Cindy, the new owner, has made several updates to the house, deck and dock which enhanced the property since our 2013 visit. It is clean, comfortable and well furnished. We thoroughly enjoyed ourselves and the location couldn't be better! Thank you Cindy for being so responsive! We will be back again soon!

    $472

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    Private Beachfront Paradise

    Matecumbe Key house
    4 BR / 3 BA / Sleeps 8 | Quick view
    Excellent9 Reviews

    Details

    Reviews

    (9)

    Beautiful two story home ......four bedroom three baths.....on your private white sandy Beachfront property with large pool facing the ocean. First floor is independent with a very large one bedroom, bar with wine cooler full bath, living, dinning and new kitchen. The covered patio is huge at 60X15. The second floor…
    • Waterfront
    • Ocean or water views
    • Hot Tub/Jacuzzi
    • Sauna
    • Internet Access
    • Pet friendly - ask
    • Suitable for children
    • Suitable for the elderly
    • Wheelchair accessible

    Details

    Reviews

    (9)

    Great House and Great Property Owner

    Left on Dec 06, 2013 for a stay in November 2013

    My family and I had the pleasure of staying at this home during Thanksgiving week. Not only did the house beat our expectations, but the communication with the owner was also fantastic. She was so helpful with every inquiry we had and went well above what we expected to make sure our time in Islamorada was as well as it could be.

    The house itself was extremely clean, beautiful and very …

    $122

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    Florida Keys Bayside Retreat

    Islamorada condo
    1 BR / 1 BA / Sleeps 4 | Quick view
    Excellent18 Reviews

    Details

    Reviews

    (18)

    Get away from it all in our tranquil waterfront condo at Summer Sea in beautiful Islamorada. Fully equipped, with newly updated kitchen and bathroom, flat screen television, and stunning views of Florida Bay from our patio. Located right in the heart of all the Keys has to offer - beautiful sunsets, beaches, boating…
    • Waterfront
    • Ocean or water views
    • Sauna
    • Internet Access
    • Washing Machine
    • Suitable for children
    • Suitable for the elderly - elevator access

    Details

    Reviews

    (18)

    great girlfriends getaway

    Left on Feb 25, 2011 for a stay in April 2010

    A very comfortable clean condo with great views of the pool and bay. Neat restuarants and shopping near by,
    We can't wait to go back!

    $300

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    Luxurious Anglers Reef with Boat Slip, Pool, Ocean

    Islamorada house
    2 BR / 3 BA / Sleeps 5 | Quick view
    Excellent22 Reviews

    Details

    Reviews

    (22)

    House, 2 Bedrooms + Convertible Bed(s), 2.5 Baths (Sleeps 5) Islamorada home set in OceanFront gated community with swimming pool and private boat dock This charming home has 2 Bedrooms, 2.5 Bathrooms, A/C, Granite work tops, modern stainless steel appliances. Open porches and balconies, rich hard wood floors, …
    • Waterfront
    • Ocean or water views
    • Internet Access
    • Housekeeping Optional
    • Washing Machine
    • Suitable for children
    • Suitable for the elderly - ask

    Details

    Reviews

    (22)

    Beautiful luxury and an absolute great stay in Keys! No hesitati

    Left on Oct 18, 2012 for a stay in October 2012

    This beautiful condo in Islamorada is pristine clean, has all the updates needed and is centrally and perfectly located if staying in the Keys! Jo (the owner) made us feel like family, gave us wonderful recommendations of who to take us snorkeling, diving, kayak rental, where to eat and even went out of her way to purchase a charcoal grill so we could cook out if we wanted to stay "home". I was …

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    $165

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    FLORIDA KEYS 2 BEDROOM COTTAGE IN ISLAMORADA

    Islamorada cottage
    2 BR / 3 BA / Sleeps 4 | Quick view

    Details

    Enjoy spectacular water views from the private petite beach, large TIKI hut, boat dock and marina, You'll be just steps away from the ocean, Enjoy spectacular water views and amazing sunsets, just steps away from Founder's park with private beach, private kiddie pool,and play area plus large Olympic pool, boat ramp, …
    • Wireless Internet
    • A/C or climate control
    • Balcony or terrace
    • Parking
    • Grill
      1 / 32

      $1,750

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      Luxury Waterfront Tropical Sunset Paradise

      Islamorada house
      4 BR / 5 BA / Sleeps 10 | Quick view

      Details

      Enjoy the most beautiful sunsets on earth from this gorgeous 4bedroom,5bathroom tropical paradise. Comes complete with Bayfront pool and lounge area that will leave you breathless. Pool table, cabana, outdoor kitchen, snorkel in the backyard!!!! Seven Flat Screens and entire house wired for sound. Boat and Captain …
      • Waterfront
      • Ocean or water views
      • Internet Access
      • Washing Machine
      • Clothes Dryer
      • Pet friendly
      • Suitable for children
      • Suitable for the elderly
      • Wheelchair accessible
      1 / 21

      $428

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      Elegant Bay Harbour Condo with 50 Foot Boat Slip

      Islamorada condo
      3 BR / 3 BA / Sleeps 6 | Quick view

      Details

      Lower Matecumbe Key condo description Welcome to paradise! This beautiful three bedroom, two and a half bath end unit condominium sleeps 6 people. Master bedroom has a king bed with direct access to the water front balcony. Second bedroom has a queen bed and the third has two twin beds. Brand new flat screen HD TVs in…
      • Waterfront
      • Ocean or water views
      • Hot Tub/Jacuzzi
      • Internet Access
      • Washing Machine
      • Suitable for children
      • Suitable for the elderly - elevator access
      • Wheelchair accessible

      $800

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      Oceanfront Luxury Islamorada Estate - 4 bed/pool

      Islamorada house
      4 BR / 4 BA / Sleeps 8 | Quick view
      Excellent2 Reviews

      Details

      Reviews

      (2)

      * 7 Day Rental minimum - Saturday to Saturday * Please check the calendar prior to inquiry Sleeps 8 adults plus up to 4 children under 6 allowed (fire code regs…
      • Waterfront
      • Ocean or water views
      • Internet Access
      • Housekeeping Optional
      • Washing Machine
      • Pet friendly
      • Suitable for children
      • Suitable for the elderly
      • Wheelchair accessible - ask

      Details

      Reviews

      (2)

      Stepping into a real life postcard - loved this home

      Left on Feb 20, 2013 for a stay in August 2012

      After an amazing stay I am absolutely compelled to write
      and let others know about this gem in paradise. I wasn't
      sure what to expect, knowing it was a true historic landmark,
      but my family and I could not have been more thrilled.
      The history associated with the house is fascinating and
      my husband and I found ourselves wanting to know even
      more of the background associated with this …

      1 / 12

      $495

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      Sunny Haven Islamorada

      Islamorada house
      3 BR / 3 BA / Sleeps 7 | Quick view

      Details

      Beautiful 3 bedroom / 2 bath in the heart of Islamorada. With a pool. A short walk to Chica Lodge and Moorings Village and all the best restaurants in the Keys like Morada Bay. Located in the best location of the Florida Keys. The house has many different places to relax, lounge and forget all the anxieties of our …
      • Wireless Internet
      • Washing Machine
      • Clothes Dryer
      • Outdoor Dining Area
      • A/C or climate control
      • Suitable for children

      $258

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      Islamorada Luxury Waterfront Condo with Boat Slip

      Islamorada condo
      2 BR / 3 BA / Sleeps 6 | Quick view
      Excellent3 Reviews

      Details

      Reviews

      (3)

      Escape to Islamorada in the Florida Keys and enjoy the breathtaking gulf and ocean views from your top floor balcony in this decorator furnished, two bedroom luxurious condo. This unit located in the complex of Bay Harbour offers a private 50' boat slip, heated swimming pool, hot tub, club house, fitness center, …
      • Waterfront
      • Ocean or water views
      • Hot Tub/Jacuzzi
      • Internet Access
      • Washing Machine
      • Suitable for children
      • Suitable for the elderly - elevator access
      • Wheelchair accessible

      Details

      Reviews

      (3)

      Wonderful stay at Bay Harbour

      Left on Jan 24, 2014 for a stay in January 2014

      This condo exceeded our expectations. It was truly a home away from home. It has all the amenities you will need to have a great vacation. The kitchen is fully furnished, the condo is spacious, and the little extras like bikes, tennis rackets, and baseball gloves are an added bonus.

      Our family was happy to see a manatee and calf in the water right outside the condo!

      Pool was very …

      $250

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      Oceanfrontparadise: 509

      Islamorada condo
      2 BR / 2 BA / Sleeps 4 | Quick view
      Excellent1 Reviews

      Details

      Reviews

      (1)

      Welcome to beautiful Islamorada located in the Florida Keys. Islamorada is known as the "Sport Fishing Capital of the World". Our ocean contains the world's most sought-after gamefish including tuna, dolphin, Marlin, permit, tarpon and bonefish. In addition to fishing, Islamorada is a favorite of divers too. Our …
      • Waterfront
      • Internet Access
      • Housekeeping Optional
      • Washing Machine
      • Clothes Dryer
      • Smoking allowed - ask
      • Suitable for children
      • Suitable for the elderly
      • Wheelchair accessible

      Details

      Reviews

      (1)

      We had fun

      Left on Nov 16, 2014 for a stay in November 2014

      my husband and 2 friends stayed in this unit for 4 days and 3 nights. they found the condo to be clean, plenty of space and conveniently located.

      they would definitely stay here again!!

      $500

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      Venetian Tropics 3 bedroom pool home on canal or d

      Islamorada house
      3 BR / 3 BA / Sleeps 8 | Quick view
      Excellent23 Reviews

      Details

      Reviews

      (23)

      Private heated pool vacation home located on deep canal with immediate access to ocean and bay. Mile Marker 86 in prestigious Venetian Shores. Pet friendly Vacation Rental License. No VR-001 106 San Remo Drive, Islamorada, Florida, 33036 Please email VenetianTropics@aol.com for the application. Weekly vacation rental…
      • Waterfront
      • Ocean or water views
      • Internet Access
      • Washing Machine
      • Clothes Dryer
      • Pet friendly
      • Suitable for children
      • Suitable for the elderly - ask

      Details

      Reviews

      (23)

      Favorite trip ever

      Left on Mar 01, 2011 for a stay in April 2007

      This was the best vacation we ever had, and it had much to do with this rental ! We drove from Maryland and pulled our boat. It was great being able to put it in the water and have it right behind where we stayed. The home was beautiful, clean and well equipped for vacationing !!! The kids loved the pool !!! We will Definetly be back !!!

      $159

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      Sues Promise - New on the Market

      Matecumbe Key villa
      1 BR / 1 BA / Sleeps 4 | Quick view
      Excellent19 Reviews

      Details

      Reviews

      (19)

      Two villas conveniently located at MM 75.5 with bay or garden views you are just minutes from boat ramps, great restaurants, beaches, shopping, fishing, snorkeling etc. Key West is only 75 miles away- an easy day trip! Private beach and boat basin. Bring your boat. Fish, swim, kayak or snorkel from the dock. Queen …
      • Waterfront
      • Ocean or water views
      • Wireless Internet
      • Washing Machine
      • Clothes Dryer
      • Suitable for children
      • Suitable for the elderly - ask

      Details

      Reviews

      (19)

      Wonderful paradise get away

      Left on Apr 07, 2012 for a stay in July 2011

      Are family of four stayed last summer. We enjoyed the comfort of the rental, the beauty of the dock and gardin, the kindness of Charles the owner and the ideal location in the Keys. It's just a perfect vacation spot for anyone who loves nature.

      $185

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      Islamorada 2-bedroom Condo

      Islamorada condo
      2 BR / 2 BA / Sleeps 6 | Quick view
      Very Good4 Reviews

      Details

      Reviews

      (4)

      If you’ve been to Islamorada you know it as the sportfishing capital of the world, a place where you’ll find every water-related activity imaginable, with fine restaurants to crab shacks serving local fare, and plenty of nightlife for both the young and young at heart. If you’ve never been here, a tropical …
      • Waterfront
      • Ocean or water views
      • Internet Access
      • Housekeeping Optional
      • Washing Machine
      • Suitable for children
      • Suitable for the elderly
      • Wheelchair accessible

      Details

      Reviews

      (4)

      Fantastic Views

      Left on Jun 06, 2012 for a stay in February 2011

      This 6th floor unit has all you need for a relaxing vacation. Close proximity to local attractions and fantastic Seafood Restaurants. The Hospital is one mile from the condo and has an excellent rehab and emergency. The complex has a private heated poool, work out room and sauna. The grounds are cleaned every morning and the manager responds to needs promptly. We will again stay here in …

      1 / 9

      $143

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      Oceanview Islamorada Florida Keys

      Islamorada apartment
      2 BR / 4 BA / Sleeps 4 | Quick view

      Details

      This oceanfront condo in Islamorada Florida (Keys) is located at mile marker 90. It is the best ocean view from everyroom and is on the 4th floor. IT IS A ONE WEEK MINIMUM AND 4 PERSON MAXIMUM BY LICENSE. ..It has all tiled floors, newly painted, new AC, and has all the conveniences of home. There is a full kitchen…
      • Wireless Internet
      • A/C or climate control
      • Central heating
      • Balcony or terrace
      • Parking
      • Suitable for children
      • Suitable for the elderly - elevator access
      • Wheelchair accessible
      1 / 20

      $250

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      Oceanfrontparadise: 209

      Islamorada condo
      2 BR / 2 BA / Sleeps 4 | Quick view

      Details

      Welcome to beautiful Islamorada located in the Florida Keys. Islamorada is known as the "Sport Fishing Capital of the World". Our ocean contains the world's most sought-after gamefish including tuna, dolphin, Marlin, permit, tarpon and bonefish. In addition to fishing, Islamorada is a favorite of divers too. Our …
      • Balcony or terrace
      • Linens Provided
      • Towels Provided
      • Freezer
      • Microwave
      • Pet friendly - ask
      • Smoking allowed - ask
      • Suitable for children - ask
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask

      $429

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      The Perfect Getaway

      Islamorada house
      4 BR / 3 BA / Sleeps 10 | Quick view
      Very Good2 Reviews

      Details

      Reviews

      (2)

      This pretty, four-bedroom, three-bath house is conveniently located in the heart of Islamorada, the fishing capital of the world. Situated in a pretty upscale neighborhood of all waterfront homes, the house is equipped with all the comforts of home. It is additional tidy and modernly furnished. Upstairs there are …
      • Hot Tub/Jacuzzi
      • Internet Access
      • Washing Machine
      • A/C or climate control
      • Patio
      • Suitable for children
      • Suitable for the elderly - ask

      Details

      Reviews

      (2)

      House had everything we needed for a Keys vacation!

      Left on Jul 14, 2013 for a stay in July 2013

      The Perfect Getaway is an appropriate name for this house; it had everything needed for a perfect vacation getaway in the Keys. The pool and hot tub were great to cool off from the afternoon sun. The dock was large enough to fit our kayak, wave runner and 21' boat. The house was clean and had all the amenities/accessories needed for a house stay.

      $1,500

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      Ocean-Front Caribbean Home.

      Islamorada house
      3 BR / 3 BA / Sleeps 10 | Quick view
      Excellent1 Reviews

      Details

      Reviews

      (1)

      The Royal Palm, South - Ocean Front Home Catch Bonefish and Tarpon from Our 450-Foot Fishing Pier. Inspired by owner Phil Sena —with nothing compromised— this luxurious Caribbean home is on the ocean's edge with 180 degrees of unobstructed ocean views and sunrises. Complete …
      • Smoking allowed
      • Suitable for children - ask
      • Suitable for the elderly
      • Wheelchair accessible

      Details

      Reviews

      (1)

      This Place Is Very Special.

      Left on Apr 24, 2015 for a stay in April 2015

      Rolled out of bed early every day this week with my boys and family friends for my favorite commute: 50 yard walk to a private boat slip at the resort.

      We rented a boat locally this year to do some fishing with our boys, hoping to get something on the grill. Three hours later, our boys had caught Mahi Mahi, Tuna, Wahoo, and even a surprise Sailfish. A lifetime memory for all. Meanwhile, the …

      1 / 14

      $397

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      Islamorada getaway home with private boat dock.

      Islamorada house
      2 BR / 3 BA / Sleeps 5 | Quick view

      Details

      This property is a single family home with a boat dock included in the price. Not a condo. Note: we only offer 7 day minimum stays with 4PM Saturday check ins and 10 AM checkouts. Maximum number of guests is 5. No pets, No smoking and maximum guests is strictly enforced by onsite security. Rates start at $2,775 per…
      • Wireless Internet
      • Washing Machine
      • Clothes Dryer
      • A/C or climate control
      • Central heating
      • Suitable for children
      1 / 10

      $167

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      One of the best views in Islamorada

      Islamorada condo
      2 BR / 2 BA / Sleeps 4 | Quick view

      Details

      Imagine waking to the beauty of a sunrise brimming over the aqua seas. Linger in your master suite and watch the ocean shift through a prism of aqua, blues and emerald greens. Gentle breezes waft through this two bedroom, two bath condo with comfortable appointments and an elegant sea glass tiled kitchen. …
      • Waterfront
      • Ocean or water views
      • Hot Tub/Jacuzzi
      • Sauna
      • Internet Access
      • Suitable for children - ask
      • Suitable for the elderly
      • Wheelchair accessible - ask

      $63

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      THE PALMS 417

      Islamorada condo
      1 BR / 2 BA / Sleeps 4 | Quick view
      Excellent1 Reviews

      Details

      Reviews

      (1)

      Minimum Rental: 1 Month Everything in this unit is exquisite - furnishings, linens, updated kitchen, appliances, and bathrooms. Great views of Florida Bay and our fabulous Keys sunsets. This complex is conveniently located just steps from a full service marina and 2 highly acclaimed restaurants. Watch the sun …
      • Ocean or water views
      • Shared outdoor pool (unheated)
      • Hot Tub/Jacuzzi
      • Balcony or terrace
      • Fitness Room
      • Suitable for children - ask
      • Suitable for the elderly - ask

      Details

      Reviews

      (1)

      Paradise on the ocean

      Left on Apr 15, 2014 for a stay in March 2014

      We rented Palm 417 for the month of March 2014. The condo has been very nicely updated and although not direct ocean front view; it does have partial view of the ocean side and a good view of the bay side with amazing sunsets. People in surrounding condos were very friendly; and one condo owner gave us some lovely smoked fish. Some road noise but we soon got used to it as the condo and location …

      $149

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      SUNSHINE PLACE

      Islamorada villa
      1 BR / 1 BA / Sleeps 3 | Quick view
      Excellent3 Reviews

      Details

      Reviews

      (3)

      Minimum Rental: 7 Nights You can have it all – privacy and convenience. The owners of this wonderful property called Sunshine Place are willing to share a portion of their piece of Paradise with you. The ground level living area of this home is perfect for one or two people who treasure the tropical atmosphere …
      • Internet Access
      • Patio
      • Parking
      • Grill
      • Refrigerator
      • Pet friendly
      • Suitable for children - ask
      • Suitable for the elderly - ask

      Details

      Reviews

      (3)

      Awesome place!

      Left on Jul 08, 2013 for a stay in July 2013

      My wife and I just returned from a weeklong stay at this property. I have to say this is far and away the nicest 1 bedroom rental and as far as I'm concerned a hidden jewel in Islamorada. It is the bottom floor of a 2 story home that has been converted to a rental unit. The upper unit is the occasional getaway of the owner and not available to rent at this time. The property entrance is gated and…

      $107

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      Islamorada Tropical Escape! Clean, Affordable & Li

      Islamorada condo
      2 BR / 2 BA / Sleeps 6 | Quick view
      Excellent11 Reviews

      Details

      Reviews

      (11)

      Escape from the world in this beautiful island paradise.Plenty of room to spread out in a two bedroom condo. Relax by the heated pool overlooking the turqoise bay; fish from the dock, snorkel in the protected cove. Kids can play in the game room or playground. Enjoy the clear, turquoise waters, breathtaking views, …
      • Waterfront
      • Ocean or water views
      • Internet Access
      • Washing Machine
      • Clothes Dryer
      • Suitable for children
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask

      Details

      Reviews

      (11)

      Great vacation!

      Left on Jan 17, 2012 for a stay in January 2012

      The condo was very convienient, well equipped, comfortable and clean. With a four year old and a five month old, we had plenty of room, pack and play available, and some Disney/Sprout for the rainy afternoon was great! Had lots to do in the area and had a great time!

      $640

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      Islamorada Oceanfront Executive Rental

      Islamorada house
      5 BR / 4 BA / Sleeps 9 | Quick view
      Excellent4 Reviews

      Details

      Reviews

      (4)

      Millionaire's Row! Beautiful home with private heated swimming pool directly on the ocean in Islamorada. This home offers excellent views of the ocean from many rooms. 5 bedroom, 4 bath owners home is beautifully furnished with ocean views from patio, living room (upper and lower), and dining room and ready to move …
      • Waterfront
      • Ocean or water views
      • Internet Access
      • Washing Machine
      • Clothes Dryer
      • Suitable for children
      • Suitable for the elderly - ask

      Details

      Reviews

      (4)

      location

      Left on Feb 08, 2012 for a stay in May 2011

      This is a very comfortable home in the best location in the keys. Great pool and fantastic pier with good fishing.Plenty of good restaraunts and bars nearby. Very good service from rental agency, any problems (minor) we have had have been taken care of promplty. We have rented this home for 6 years in a row and going back in May.

      $158

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      FYC -updated condo - excellent location -Marina

      Islamorada condo
      2 BR / 2 BA / Sleeps 6 | Quick view
      Excellent1 Reviews

      Details

      Reviews

      (1)

      This magnificent two bedroom, two bath Condo, sleeps six comfortably. Newly decorated & tastefully furnished with wood floors throughout. Fully-equipped kitchen with new appliances. Flat Screen TV with Digital sound, DVD, stereo and CD player. WIFI included !!! Outside patio and laundry just steps away.. We have …
      • Waterfront
      • Ocean or water views
      • Internet Access
      • Washing Machine
      • Clothes Dryer
      • Suitable for children
      • Suitable for the elderly

      Details

      Reviews

      (1)

      Beautiful, comfortable condo

      Left on Jan 06, 2014 for a stay in December 2013

      I traveled with my partner and another couple. We enjoyed the comfortable roomy accomodations. Loved the convenience of cooking meals. The grounds are beautiful. We enjoyed the pool that is newly refreshed. Easy access to the beach area to watch New Year's fireworks was great. The owner was available by phone to answer any questions we had. We plan on renting again.

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      $67

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      THE PALMS 309

      Islamorada house
      2 BR / 2 BA / Sleeps 5 | Quick view

      Details

      MINIMUM STAY: 29 DAYS Exceptional condo with panoramic views of the Atlantic Ocean. This condo is in one of the most popular condo complexes in Islamorada - The Palms of Islamorada. Comfortably furnished and ready for your arrival this unit offers an updated kitchen with Corian counters, updated cabinetry and a …
      • Shared outdoor pool (unheated)
      • Hot Tub/Jacuzzi
      • Internet Access
      • Balcony or terrace
      • Fitness Room
      • Suitable for children - ask
      • Suitable for the elderly - ask

      $115

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      Bay Front Condo, Marina & Dockage in Islamorada,FL

      Islamorada condo
      3 BR / 2 BA / Sleeps 6 | Quick view
      Excellent9 Reviews

      Details

      Reviews

      (9)

      Escape to paradise in the fabulous Florida Keys at Futura Yacht Club. This rental property is a private gated community with a 65 slip deep water marina. This tropical waterfront community offers world class fishing and diving, 2 lighted tennis courts, heated pool, private beach, basketball and dockage for your boat…
      • Waterfront
      • Ocean or water views
      • Internet Access
      • Outdoor Dining Area
      • A/C or climate control
      • Smoking allowed - ask
      • Suitable for children
      • Suitable for the elderly
      • Wheelchair accessible

      Details

      Reviews

      (9)

      Great Stay

      Left on Nov 08, 2011 for a stay in September 2011

      The condo was very clean and updated! Glenn was very helpful with our stay. We even went fishing on the Reel Sharp and caught a ton of Dolphin! Us college girls will be coming again for Sailfishing season!

      $500

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      SANCTUARY IN PARADISE

      Islamorada house
      4 BR / 4 BA / Sleeps 10 | Quick view
      Excellent3 Reviews

      Details

      Reviews

      (3)

      WWW.SCHOONERHAMMOCK.COM This unique property offers : -master suite -apartment -cottage -3 full kitchens On Atlantic Ocean. Simple, sweet, and serene sanctuary. Please contact Andy Cancela 828 808 1693 We love The Lord and look forward to sharing our home with you.
      • Waterfront
      • Ocean or water views
      • Hot Tub/Jacuzzi
      • Internet Access
      • Housekeeping Optional
      • Pet friendly
      • Suitable for children
      • Suitable for the elderly

      Details

      Reviews

      (3)

      Amazing Experience and even more Amazing Hosts

      Left on Aug 20, 2014 for a stay in May 2014

      This was the best family vacation! The home was beautiful and comfortable. Definitely something you would call home away from home.The property was perfect for each person in our family to find bliss. Just minutes away from grocery stores, bate shops and restaurants. Fishing (plenty of mangroves and tarpon) and snorkeling right off the dock, laziness in the hammocks, a relaxing hot tub and plenty…

      1 / 9

      $163

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      Islamorada, Florida Keys (Beacon Reef MM87)

      Islamorada condo
      2 BR / 2 BA / Sleeps 4 | Quick view

      Details

      Available: November: 4950 January through May: $5000 single month, three or more months $4900.each month PLEASE DO NOT SUBMIT A REQUEST FOR A PERIOD LESS THAN ONE FULL MONTH KINDLY NOTE: MONTHLY RENTAL. To maintain the beauty of Beacon Reef, rental contracts must be for no less than a month. This helps keep…
      • Waterfront
      • Ocean or water views
      • Hot Tub/Jacuzzi
      • Housekeeping Optional
      • Washing Machine
      • Pet friendly - ask
      • Suitable for children
      • Suitable for the elderly - elevator access
      • Wheelchair accessible - ask

      $2,000

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      Studio condo in Islamorada

      Islamorada condo
      1 BA / Sleeps 4 | Quick view
      Very Good6 Reviews

      Details

      Reviews

      (6)

      This is a tastefully decorated, fully air-conditioned studio unit with a full bathroom, completely tiled. It offers a queen-sized Murphy bed that can be easily stowed away during the day. On the fully screened and enclosed balcony you will find a glass-top table with two chairs, ceiling fan, TV, single-sized sleeper …
      • Sauna
      • Internet Access
      • Washing Machine
      • Clothes Dryer
      • A/C or climate control
      • Suitable for children
      • Suitable for the elderly
      • Wheelchair accessible

      Details

      Reviews

      (6)

      magic

      Left on Mar 17, 2011 for a stay in January 2011

      spent 3 weeks in condo islamorada , we rented from victoria furdui , from start to finish everything was terriffic we had a ball , loved every second of our holiday . only problem was we could not bring sunshine back to ireland.
      the condo was very clean , neat , no problems at all . the location is very good easy to get to sea side and shopping in miami . highly recommend this place . jim julie …

      $3,000

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      2-bed,1.5-bath Condos On The Bay, Islamorada

      Islamorada condo
      2 BR / 2 BA / Sleeps 4 | Quick view
      Average3 Reviews

      Details

      Reviews

      (3)

      Complex Amenities - MM 88.5 - Building has five floors - Large swimming pool & children's pool - Exercise room with sauna - Laundry room on each floor - Billiard and Ping-Pong room - Adult party lounge - Cookout facilities - Direct access to Florida Bay and then ocean - Minutes from Islamorada, “sport fishing …
      • Waterfront
      • Ocean or water views
      • Sauna
      • Washing Machine
      • Clothes Dryer
      • Suitable for children
      • Suitable for the elderly
      • Wheelchair accessible

      Details

      Reviews

      (3)

      Beautiful Vacation Spot- Great for families!

      Left on Apr 18, 2013 for a stay in April 2013

      The condo in Islamorada was clean, updated, and nicely furnished, perfect for our family of 4. The kitchen is updated with granite counters & stainless steel appliances. The view from the living area in the condo is simply gorgeous-crystal clear water. There is a cozy little deck for drinking coffee in the morning and watching sunsets in the evening. The master bedroom has a king size bed, …

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      $250

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      Angler's Reef Coastal Conch Style Vacation Home

      Islamorada cottage
      2 BR / 3 BA / Sleeps 6 | Quick view

      Details

      This Coastal Conch Style Cottage has been recently updated to accommodate vacation renters and their families. The cottage has all new furnishings and accessories that offers a "home away from home" feel. The Coastal style conch cottage is located in the gated community, ocean front resort development of Angler's Reef…
      • Suitable for children
      • Suitable for the elderly
      1 / 17

      $120

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      75651 Overseas Hwy Islamorada Fla Keys Oceanfront

      Matecumbe Key condo
      2 BR / 1 BA / Sleeps 4 | Quick view

      Details

      Directly on your private oceanfront beach. Ocean views from every room of your two bedroom one bath Keys style duplex villa. You will experience the true 'old Keys' charm of bird watching on the wraparound deck to fishing on the beach...or perhaps just relaxing on the sand. With over a half acre of tropical landscape…
      • Private Beach
      • Ocean or water views
      • Internet Access
      • Housekeeping Optional
      • Washing Machine
      • Pet friendly - ask
      • Smoking allowed - ask
      • Suitable for children - ask
      • Suitable for the elderly - ask
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