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$92

3 BR / 2 BA / Sleeps 8

7 Reviews

$92

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Family Friendly Executive Bay**Discounts Available**

Islamorada house
3 BR / 2 BA / Sleeps 8 | Quick view
“ Excellent ” 7 Reviews

Details

Reviews

(7)

Beautiful three bedroom bay side townhouse with private beach access in sunny Islamorada (near Key Largo). Welcome to our little slice of paradise! Come and relax at our beautiful townhome in the Florida Keys. The Executive Bay Club is located in Islamorada, the Sport Fishing Capital of the World. It is a private, …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(7)

Wonderful

Left on Jul 20, 2013 for a stay in June 2013

This rental by far was one of the best rentals we have stayed at. The location and the house were perfect! The house is very large and everything you can imagine has been supplied. The pool, community center, tennis courts and complex in general were beautiful and well maintained. Really good experience!

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$99

2 BR / 2 BA / Sleeps 8

2 Reviews

$99

Inquire

Newly Renovated Townhouse in Beautiful Executive Bay **Discounts Available**

Islamorada condo
2 BR / 2 BA / Sleeps 8 | Quick view
“ Excellent ” 2 Reviews

Details

Reviews

(2)

Beautiful two bedroom townhouse on the Bay side with private beach access in sunny Islamorada (near Key Largo). Welcome to our little slice of paradise! Come and relax at our beautiful, newly renovated townhome in the Florida Keys. The Executive Bay Club is located in Islamorada, the Sport Fishing Capital of the World…
  • Shared outdoor pool (unheated)
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

Great condo, perfect location!

Left on Jan 02, 2015 for a stay in December 2014

I have two small children and the condo was perfect and comfortable for the entire family. It was nicely remodeled. The pool and dock area were very nice. Security was visible and very friendly. The location was close to everything. The property management service was excellent. We had a wonderful family vacation and will definitely be returning next year!

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$215

3 BR / 2 BA / Sleeps 7

2 Reviews

$215

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Gorgeous Keys Water Front Home with Private Dock and Ramp

Islamorada house
3 BR / 2 BA / Sleeps 7 | Quick view
“ Excellent ” 2 Reviews

Details

Reviews

(2)

Water Front home, located Oceanside in Lower Matecumbe key, Islamorada mile marker 73, (The Sport Fishing Capital of the World). 15' wood dock and 12’ wide ramp, so bring your own boat and enjoy the sun!! Easy canal access to the ocean. Maximum boat size is 27'. Only 1 boat allowed. There is a covered fish cleaning …
  • Ocean or water views
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

Great Getaway!

Left on Dec 09, 2014 for a stay in June 2014

This property was great! It was nicely stocked, very comfortable beds. I loved being on the water! Excellent place to stay! I will return again next summer.

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$400

3 BR / 3 BA / Sleeps 8

1 Reviews

$400

Inquire

Oasis (28 Day Minimum Only)

Islamorada house
3 BR / 3 BA / Sleeps 8 | Quick view
“ Excellent ” 1 Reviews

Details

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

Details

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…

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$663

5 BR / 6 BA / Sleeps 10

Pineapple Plantation (28 Day Minimum) - Islamorada vacation rentals
1 / 15

$663

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Pineapple Plantation (28 Day Minimum)

Islamorada house
5 BR / 6 BA / Sleeps 10 | Quick view

Details

****This house cannot rent for less than 28 days, per County Ordinance**** Breathtaking Sunset's, Breathtaking Home. Pineapple Plantation is an unbelievable gated, New Bay Front home. It is perfectly located a Mile Marker 89, Islamorada. Boasting 5 Bedroom Suite's, Gourmet kitchen with an ocean view, Dining Room that…
  • Waterfront
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask

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$358

4 BR / 3 BA / Sleeps 8

4 Reviews

$358

Inquire

76004 Overseas Highway

Islamorada house
4 BR / 3 BA / Sleeps 8 | Quick view
“ Excellent ” 4 Reviews

Details

Reviews

(4)

Enjoy spectacular sunsets while drinking margaritas on the observation deck of this stunning home nestled back behind swaying palm trees. Large sandy beach and great dock. Interior photos available! Mile Marker 76, Bayside. Home has 2 bedrooms & 2 bathrooms upstairs, and a separate 2 bedroom, 2 bathroom apartment …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(4)

A Week in a Tropical Paradise.

Left on Aug 03, 2010 for a stay in July 2010

We had a fantastic time. Incredible home on the water with boat dock. Plenty of room and privacy. Accommodations were five star. We highly recommend it.

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$429

0 BR / 0 BA / Sleeps 4

1 / 27

$429

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75691 Overseas Hwy

Islamorada house
0 BR / Sleeps 4 | Quick view

Details

With the weather getting hotter, the water is once again the place to be in South Florida. Fortunately, you'll barely have to venture out your back door to take a soak while vacationing at this quaint oceanfront conch house. Located on Islamorada's Lower Matecumbe Key, near mile marker 76, this traditional one-story …
  • Waterfront
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$500

4 BR / 3 BA / Sleeps 8

9 Reviews

$500

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Private Beachfront Paradise

Matecumbe Key house
4 BR / 3 BA / Sleeps 8 | Quick view
“ Excellent ” 9 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 …

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$380

3 BR / 3 BA / Sleeps 6

3 Reviews

$380

Inquire

75333 Overseas Hwy

Matecumbe Key house
3 BR / 3 BA / Sleeps 6 | Quick view
“ Excellent ” 3 Reviews

Details

Reviews

(3)

Exceptional oceanfront home equipped with a sandy beach and forever views! Exquisite design and rich appointments compliment this oceanfront home in Lower Matecumbe, (mile marker 75, South Islamorada). You will enjoy private terraces from each bedroom overlooking picturesque sunrises and panoramic views of the open …
  • Internet Access
  • Microwave
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(3)

Heaven on Earth

Left on Jan 30, 2013 for a stay in December 2012

My husband and I rented this home for the week of Christmas. We also invited our respective parents. This is the most peaceful home in Islamorada. Centrally located to the upper and lower keys.

There home is well appointed with everything you need except for the groceries and tolietries that you will need. All appliances work well and the home is in excellent condition.

Freewheeler realty…

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$250

3 BR / 3 BA / Sleeps 8

1 / 9

$250

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Three story home 100 feet deep water dock big pool

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

Details

Please contact us if you have any policy questions since we do not agree with this website forcing us to choose policies they dictate. We have our own polices so please ignore what's posted in the policies section on this website. Also please visit our website at www.KeysRentalHouse.com Beautiful three story luxury …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Suitable for children
  • Suitable for the elderly

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$117

2 BR / 3 BA / Sleeps 4

2 Reviews

$117

Inquire

75190 Overseas Hwy - 28 NIGHT MINIMUM!!!!!!!

Matecumbe Key house
2 BR / 3 BA / Sleeps 4 | Quick view
“ Excellent ” 2 Reviews

Details

Reviews

(2)

Great home with an even better view ... come and stay for a month and enjoy the Incredible endless views from the patio. Home is located in the perfect spot for snorkeling, fishing, and diving, and has a protected & private boat basin! Come once and you will see why so many people come back year after year to …
  • Ocean or water views
  • Internet Access
  • A/C or climate control
  • Grill
  • Dishwasher
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

Relaxing

Left on Aug 18, 2011 for a stay in July 2011

The location was great.Mad Dog's & Ziggy's was fabulous! Love shopping at Morada Bay Gallery. The kitchen was ill equipped, who ever heard of a house in the Keys w/o a blender??? Nasty grill. The beach at the house was great. The gate to the house was locked and we were not supplied the key and had to wait for 45 minutes for someone to bring us one.

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$100

2 BR / 2 BA / Sleeps 4

2 Reviews

$100

Inquire

157 Ojibway Ave - 28 NIGHT MINIMUM

Islamorada house
2 BR / 2 BA / Sleeps 4 | Quick view
“ Very Good ” 2 Reviews

Details

Reviews

(2)

This 2Bed/2Bath stilt home is located at mile marker 89 at the very end of Indian Waterways subdivision. Located on a canal with approximately 30' of dockage, you'll have almost immediate access to the Florida Bay and just a 7 minute boat ride to Tavernier Creek, which takes right over to the Atlantic Ocean. The yard …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

Very nice and relaxing...

Left on Feb 23, 2011 for a stay in January 2011

Very nice...my 3rd time renting the house...no problems...excellent service...great location...I would recommend to others...hope to be back soon...

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$150

3 BR / 2 BA / Sleeps 6

1 / 1

$150

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127 Tequesta - 28 Night Minimum

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

Details

N/A
  • Waterfront
  • Ocean or water views
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$150

3 BR / 3 BA / Sleeps 6

4 Reviews

$150

Inquire

200 Plantation Shores Drive

Islamorada house
3 BR / 3 BA / Sleeps 6 | Quick view
“ Excellent ” 4 Reviews

Details

Reviews

(4)

A very charming and immaculate 3 bedroom home in Plantation Key. This home has excellent protected deep water dockage. Ocean views from balcony. Easy bay access via Tavernier Creek. Close to resturants and store. CLICK HERE to view photos on a mobile device. Additional amenities include: dock/boat-slip, coffee maker…
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Grill
  • Dishwasher
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(4)

Islamorada Getaway

Left on Sep 06, 2012 for a stay in July 2012

The service from Freewheeler Vacations, Inc was above & beyond! Our family rented the Islamorada home for the month of July 2012. The ocean breezes were fantastic! There were only two things I wish would have been better. One, the quality of the cookware and second, the aC cooling of the downstairs bedroom. If these items were to be updated/corrected then this truly would be a perfect vacation …

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$600

4 BR / 3 BA / Sleeps 8

1 Reviews

$600

Inquire

Latitude

Islamorada house
4 BR / 3 BA / Sleeps 8 | Quick view
“ Excellent ” 1 Reviews

Details

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

Details

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 …

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$250

3 BR / 1 BA / Sleeps 6

1 Reviews

$250

Inquire

The Cottage (28 DAY MINIMUM)

Islamorada house
3 BR / 1 BA / Sleeps 6 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

****DUE TO A COUNTY ORDINANCE THIS PROPERTY CANNOT RENT FOR LESS THAN 28 DAYS**** You fall in love with The Cottage at first sight. Built in 1935, this once Red Cross building serves as a true historical reflection of the Florida Keys. Both bedrooms overlook the ocean, which is a mere 30 feet from the wrap around …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

COTTAGE @ SCHOONER BAY - ABSOLUTE SOLITUDE AND SUPERB LOCATION

Left on Dec 02, 2013 for a stay in November 2013

We were so lucky to have visited this home during November. We had the whole private gated compound to ourselves and even though we only leased the Cottage, the owners were so gracious to allow us total use of the pool at the Palm house next door. I cannot say enough good things about our entire experience here. It was quiet, our main bedroom was literally 30 feet from the water, it was …

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$125

1 BR / 1 BA / Sleeps 3

6 Reviews

$125

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

Islamorada villa
1 BR / 1 BA / Sleeps 3 | Quick view
“ Excellent ” 6 Reviews

Details

Reviews

(6)

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

Details

Reviews

(6)

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 …

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$110

2 BR / 1 BA / Sleeps 4

1 / 17

$110

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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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$107

2 BR / 2 BA / Sleeps 4

1 / 20

$107

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114 Plantation Ave - 28 NIGHT MINIMUM!!!

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

Details

This charming 2 bedroom and 2 bathroom home is located at the 90 mile marker. This home is centrally located to shopping, restaurants, and grocery store. This home offers deep water dockage and easy access to the Atlantic Ocean via Tavernier Creek. Great outdoor space whether you are sitting on the porch or sitting …
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$400

3 BR / 3 BA / Sleeps 5

6 Reviews

$400

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You will never want to leave

Matecumbe Key house
3 BR / 3 BA / Sleeps 5 | Quick view
“ Excellent ” 6 Reviews

Details

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 …

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$495

3 BR / 2 BA / Sleeps 7

1 / 13

$495

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Sunny Haven Islamorada

Islamorada house
3 BR / 2 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. Relax by the pool or relax in the garden or relax under the shade of the pergola by the …
  • Wireless Internet
  • A/C or climate control
  • Central heating
  • Balcony or terrace
  • Parking

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$100

2 BR / 2 BA / Sleeps 4

2 Reviews

$100

Inquire

122 Leoni Dr - 28 night Minimum!!!

Islamorada house
2 BR / 2 BA / Sleeps 4 | Quick view
“ Very Good ” 2 Reviews

Details

Reviews

(2)

Modest home in great subdivision. Excellent, deep dockage on a wide canal with easy ocean and bay access via Snake Creek. Cool tropical breezes can be enjoyed on the screened in porch. Minimum Stay for this home is 28 night minimum. Wirelss internet. Click Here for Map! CLICK HERE to view photos on a mobile device…
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

Very good service from Freewheeler

Left on Jun 22, 2010 for a stay in May 2010

Only thing missed was internet access. Otherwise a good stay.

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$83

2 BR / 2 BA / Sleeps 4

1 / 19

$83

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135 Gulfview Dr - 28 Night Minimum!!!!

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

Details

This delightful 2 bedroom, 2 bathroom home is located in Port Antigua (south Islamorada) at the 74 mile marker. While not located directly on the bay, you'll still be able enjoy the homeowners park that has a beach and beautiful sunsets. The home comes equipped with Wi-Fi internet. Click here to view photos on a …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$215

3 BR / 2 BA / Sleeps 6

16 Reviews

$215

Inquire

Windy Cove Townhomes

Islamorada condo
3 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 16 Reviews

Details

Reviews

(16)

Please send us an inquiry or call us for availability. We have a couple of units. Located on Windley Key this gated 5 unit complex has the best of the Keys with a private pool, sandy beachy area, and fishing pier with flats boat dockage (drawing 24" or less) located directly on the ocean. Amazing views!. We …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • A/C or climate control
  • Central heating
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(16)

Absolutely awesome

Left on Jun 21, 2010 for a stay in June 2010

Windy Cove was a wonderful place.
The view was amazing. The location was perfect. We will be staying here again!

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$715

4 BR / 3 BA / Sleeps 10

1 / 38

$715

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82754 Overseas Highway

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

Details

OSPREY BAY VILLA! Wonderful bayfront home in the heart of Islamorada in the fabulous Florida Keys for rent by the week or monthly. Offering 5 bedrooms and 3 full baths on 2 living levels overlooking the Florida Bay with its incredible sunset views. Sleeps 10 people comfortably. Spacious fully equiped kitchen with the …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fireplace
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$800

4 BR / 4 BA / Sleeps 8

2 Reviews

$800

Inquire

Oceanfront Luxury Islamorada Estate - 4 bed/pool

Islamorada house
4 BR / 4 BA / Sleeps 8 | Quick view
“ Excellent ” 2 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 …

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$100

2 BR / 2 BA / Sleeps 4

1 / 7

$100

Inquire

Executive Bay Club

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

Details

Please send us an inquiry or call us for availability. Prices vary on the units. 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 fishing/boat dock. Next …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$329

3 BR / 3 BA / Sleeps 6

6 Reviews

$329

Inquire

138 Bayview Isle

Islamorada house
3 BR / 3 BA / Sleeps 6 | Quick view
“ Very Good ” 6 Reviews

Details

Reviews

(6)

Modern canal home with views of Snake Creek. The property is completely fenced in. Third level master suite with private master balcony. Well furnished with all the extras. Easy ocean or bay access and dockage up to 50 feet. Open floor plan with regulation pool table and screened in porch. This home's entertainment …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(6)

Perfect location

Left on May 27, 2011 for a stay in May 2011

Other then having to Clean-up the bug's it was great.

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$100

2 BR / 2 BA / Sleeps 4

2 Reviews

$100

Inquire

Summer Sea Condominium Complex

Islamorada condo
2 BR / 2 BA / Sleeps 4 | Quick view
“ Excellent ” 2 Reviews

Details

Reviews

(2)

Summer Seas is located directly on the Florida Bay is the perfect sunny getaway! The complex is centrally located at mm 88. There is also on-site community laundry, a pool, hot tub, and clubhouse. Islamorada, the "Village of Islands," is widely known as the sportfishing capital of the world. Its islands …
  • Waterfront
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • A/C or climate control
  • Parking
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

Heaven in Islamorada, Florida

Left on Aug 23, 2011 for a stay in July 2011

Rented a 2/2 condo for the month of July 2011.
Great location, nice amenities,clean,wonderful view, friendly staff and condo owners.
Excellent price.
I will definitely do this again soon.

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$300

2 BR / 2 BA / Sleeps 6

3 Reviews

$300

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Islamorada Florida Keys Beautiful 2B 2B Townhouse

Islamorada villa
2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 3 Reviews

Details

Reviews

(3)

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 …
  • Waterfront
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Suitable for children

Details

Reviews

(3)

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 …

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$143

2 BR / 0 BA / Sleeps 4

3 Reviews

$143

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Sea Gulls Condominium Complex

Islamorada condo
2 BR / Sleeps 4 | Quick view
“ Excellent ” 3 Reviews

Details

Reviews

(3)

Please send us an inquiry or call us for availability. Prices vary on the units. Sea Gulls Condominiums, on the shores of the Atlantic Ocean provides vacationers the splendor of the Atlantic waters with luxury living at an affordable price. This perfect family vacation destination offers something to do in, under, …
  • Waterfront
  • Ocean or water views
  • Sauna
  • Internet Access
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(3)

Adequate

Left on May 24, 2012 for a stay in April 2012

The condo provided plenty of space for two couples. The complex is quiet. The pool is nice and the meditation beach(tiny) was relaxing. The condo itself was very dated. The beds were comfortable. The living room furniture was stained. The entire condo had an odor but tolerable. Possibly it had not been used for some time, not sure. Smelled musky. The balcony is large and was enjoyable for…

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$117

3 BR / 2 BA / Sleeps 6

1 / 1

$117

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258 Mohawk St - 28 Night Minimum!!!!!!!

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

Details

Looking for an extended stay in the Upper Keys that won't bust the bank? If so, you need not search any farther than this cozy, modern home on Islamorada's Plantation Key. Located in the popular Indian Waterways neighborhood, this three-bedroom/two-bath house is a great value at just $3,500 per month. The residence …
  • Waterfront
  • Internet Access
  • A/C or climate control
  • Porch
  • Grill
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$315

2 BR / 3 BA / Sleeps 4

1 / 1

$315

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Angler's Reef | 130 Anglers Way

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

Details

Add some Caribbean spice to your next visit to the Florida Keys. This two-bedroom/two-and-half bath villa sits within Angler's Reef, a charming community of detached town homes that take their inspiration from the architecture of the British West Indies. Located at mile marker 85, on Windley Key, it's the perfect …
  • Ocean or water views
  • Internet Access
  • Clothes Dryer
  • A/C or climate control
  • Central heating
  • Suitable for children
  • Suitable for the elderly - ask

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$300

2 BR / 3 BA / Sleeps 5

22 Reviews

$300

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Luxurious Anglers Reef with Boat Slip, Pool, Ocean

Islamorada house
2 BR / 3 BA / Sleeps 5 | Quick view
“ Excellent ” 22 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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$200

2 BR / 1 BA / Sleeps 4

2 Reviews

$200

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83261 Old Highway

Islamorada house
2 BR / 1 BA / Sleeps 4 | Quick view
“ Excellent ” 2 Reviews

Details

Reviews

(2)

A quaint bungalow on a not-so-quaint piece of oceanfront land right in the Heart of Islamorada! This home has two bedrooms, two bathrooms, and a lot of Keysy charm. During your stay, you will enjoy such amenities as a fishing dock with Chickee hut (1ft draft), cable television, a kayak, and a white picket fence …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

House with privats beach and fishing pier

Left on Mar 27, 2014 for a stay in March 2014

Great house; really stocked well. Huge property with a grass yard in the front, side and about half grass and sandy beach in the back. Saw a shark, stingrays, spuffer fish and baracuda from the fishing pier. Also a great location; close to everything. May be better for a couple since there is only 1 bathroom; a little tight for a family of four. Really my only complaint is they should put down…

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$2,000

0 BR / 1 BA / Sleeps 4

6 Reviews

$2,000

Inquire

Studio condo in Islamorada

Islamorada condo
0 BR / 1 BA / Sleeps 4 | Quick view
“ Very Good ” 6 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 …

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$858

5 BR / 6 BA / Sleeps 10

1 / 22

$858

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Southern Comfort

Islamorada house
5 BR / 6 BA / Sleeps 10 | Quick view

Details

Village Permit # VR-204 You can not rent this property for less than one week. Sit back, relax, a light breeze, gaze the blue waters of the Atlantic Ocean….and be lost. Southern Comfort is the perfect vacation home in the Florida Keys, located at MM 77. This very private Estate sits on 3+ acres offering 5 bedrooms…
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly

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$643

4 BR / 3 BA / Sleeps 8

1 / 34

$643

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50 Schooner Bay Rd - Aguazul

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

Details

How about sipping coffee and watching the sun come up as you fish off the end of your very own 300 foot pier? Sounds good, right? Well, that's just one reason to stage your upcoming vacation at this lovely, hacienda-style home on a quaint and private oceanfront street in Islamorada. CLICK HERE to view photos on a …
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$236

3 BR / 2 BA / Sleeps 6

2 Reviews

$236

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155 Azalea Street

Islamorada house
3 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 2 Reviews

Details

Reviews

(2)

Plantation Key canal home. Nice new home with screened porch and pool table! Delightfully furnished for a comfortable stay. Excellent outdoor entertaining space, great for soaking in the hot tub, gazing at fish in the canal, having cocktails under the Chickee, or for the kids to run around and play. Great dockage with…
  • Waterfront
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Porch
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

Loved the place and location!!

Left on Aug 11, 2013 for a stay in July 2013

We completely enjoyed our stay. Plenty of room for 6 ppl to sleep. Nice sized kitchen and dining area. We stayed with two young children and they loved it. Great location for both gulf access and on land access to grocery, dining and all. We can't wait to go back.

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$200

3 BR / 2 BA / Sleeps 8

1 Reviews

$200

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Beautiful Captain's Cove

Islamorada villa
3 BR / 2 BA / Sleeps 8 | Quick view
“ Excellent ” 1 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!

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$208

2 BR / 2 BA / Sleeps 4

2 Reviews

$208

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75130 Overseas Highway

Matecumbe Key house
2 BR / 2 BA / Sleeps 4 | Quick view
“ Excellent ” 2 Reviews

Details

Reviews

(2)

Great house in Lower Matecumbe (south side of Islamorada) at the 75 mile marker on the bayside. This house has fabulous sunset views in a nice quiet part of town. There is a small beach area in the back with palm trees giving you a little more privacy. A screened in porch with tables and chairs makes for a great …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Television
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

The view and location was excellent.

Left on May 06, 2011 for a stay in April 2011

The house had most of the amenities I would expect at a beach location. You can't beat the sunsets over the bay!
We snorkeled at Key Largo and took a day trip into key West, so the location was perfect. The area had the best restaurants. We tried them all.
Only complaints were: no outdoor grill, no wine glasses, sheets kept pulling off the bed and rusted beach chairs.

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$400

4 BR / 5 BA / Sleeps 8

2 Reviews

$400

Inquire

74920 Overseas Hwy

Islamorada house
4 BR / 5 BA / Sleeps 8 | Quick view
“ Excellent ” 2 Reviews

Details

Reviews

(2)

One of a kind bay front estate! This is an absolutely gorgeous estate home offering a gated entrance paved brick driveway, 3,500 sf, 3 bedrooms, 3.5 bathrooms upstars and a bonus 1 bedroom, 1 bathroom apartment downstairs. Enjoy ocean & lagoon views, deep water protected dockage, 2 Great rooms, private master suite, …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • A/C or climate control
  • Telephone
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

The Best

Left on May 29, 2012 for a stay in April 2012

Everything about this property was exactly as represented by Freewheeler. It was spotless and completely ready for our group despite last minute changes to the schedule. We will certainly consider this property and Freewheeler for our future visits to the Keys.

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$350

3 BR / 3 BA / Sleeps 8

3 Reviews

$350

Inquire

Enjoy stunning views of the sunrise from this beautiful Keys condo

Islamorada condo
3 BR / 3 BA / Sleeps 8 | Quick view
“ Excellent ” 3 Reviews

Details

Reviews

(3)

Revel in the beauty of the morning sunrise as you relax on your own, private lanai while sipping your morning coffee, or enjoy a meal al fresco to the sound of the waves and gulls. This piece of paradise is sure to become your favorite home away from home. This beautifully furnished and spacious condo offers all the …
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(3)

Great Vacation!

Left on Dec 22, 2014 for a stay in October 2014

We have stayed at Bay Harbor several times in this condo and love it. The condo feels like home and has everything you would ever need during your stay The complex is very well maintained and the pool area is great for relaxing, the slip for your boat is also a plus. Everything from the great fishing, snorkeling and great restaurants, there is something for everyone in the family. This will …

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$929

4 BR / 4 BA / Sleeps 10

13 Reviews

$929

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75731 Overseas Highway

Matecumbe Key house
4 BR / 4 BA / Sleeps 10 | Quick view
“ Excellent ” 13 Reviews

Details

Reviews

(13)

Islamorada is the Spiritual Center of the Keys, the Sportfishing Capital of the World, and home to the largest fleet of charter boats in the Keys. Fish deep water or the back bay. Snorkeling and SCUBA sites abound. Restaurants, art galleries, and other shopping are plentiful in Islamorada. Pass through a private …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • A/C or climate control
  • Grill
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(13)

Paradise!!!

Left on Jul 14, 2010 for a stay in May 2010

Michelle Sorell was a great help and everything was just perfect. I hated to leave. the property is well maintained and Randy was also nice with all our grandboys that came in to visit while we were there. Thanks again for making our vacation so wonderful.

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$286

3 BR / 3 BA / Sleeps 6

4 Reviews

$286

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130 Bayview Isle Dr

Islamorada house
3 BR / 3 BA / Sleeps 6 | Quick view
“ Excellent ” 4 Reviews

Details

Reviews

(4)

Great neighborhood located on Snake Creek. 2 bedroom/2 bath upstairs with a bunkroom and bath downstairs. An outdoor hot tub and sundeck complement the excellent deep water dockage and easy bay or ocean access. There is room for about a 36 foot boat or less. Mile Marker 86, Bayside. VACATION RENTAL LICENSE: VR-069 …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(4)

I loved this place!

Left on Nov 02, 2010 for a stay in October 2010

Both the home and the location in Islamorada were perfect! I spent a week at 130 Bayview Isle and it was exactly what I hoped it to be. It was incredibly quiet and felt like home. If the home is for rent next year, I will absolutely rent it again. Awesome place!

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$175

4 BR / 4 BA / Sleeps 8

1 / 36

$175

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164 Plantation Shores Drive - 28 NIGHT MINIMUM

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

Details

This is a very spacious and very well-maintained 4 bedroom, 3 bathroom home toward the mouth of the canal on a quiet street in Plantation Key (Tavernier). You and your group will enjoy stunning views from the main level, master suite, & rooftop sundeck. There is approximately 20ft concrete dockage. The home sits on a …
  • Ocean or water views
  • Internet Access
  • A/C or climate control
  • Grill
  • Dishwasher
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$758

5 BR / 3 BA / Sleeps 10

17 Reviews

$758

Inquire

87445 Old Hwy

Islamorada house
5 BR / 3 BA / Sleeps 10 | Quick view
“ Excellent ” 17 Reviews

Details

Reviews

(17)

This oceanfront home will surely get you in a Keys state of mind. Featuring five bedrooms, a pool, and an expansive private beach, its ideal for anything from a reunion of extended family or friends, to a small wedding, to a relaxing family vacation. The 4,300 square foot house will capture your attention at the …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • A/C or climate control
  • Garage
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(17)

Great Location, house needs some nimor work

Left on Apr 07, 2011 for a stay in March 2011

Nice house, dirty carpets, screens on doors need repair, with minor cleaning and repairs this house could be great

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$300

3 BR / 2 BA / Sleeps 6

2 Reviews

$300

Inquire

107 San Remo

Islamorada house
3 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 2 Reviews

Details

Reviews

(2)

Affordable Venetian Shores canal home at the Mile Marker 86, Bay-side. Nice decor, recently updated with a private downstairs apartment. Two bedroom/one bath upstairs and a one bedroom/one bath apartment downstairs (with a complete kitchen and living room). Easy ocean or bay access via Snake Creek. CLICK HERE to view …
  • Waterfront
  • Ocean or water views
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

Experience of a lifetime!

Left on Feb 09, 2014 for a stay in November 2013

Love the location, house was extremely well equipped, comfortable, Very accommodating to a wide range of taste and activities!

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$286

3 BR / 2 BA / Sleeps 6

6 Reviews

$286

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76300 Overseas Highway

Islamorada house
3 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 6 Reviews

Details

Reviews

(6)

Enjoy this Bayfront home with a spectacular sunset view, fenced yard and tile throughout the house. Also has great dockage and clean swimming area. Secured wi-fi, local telephone, & cable television (basic) included. VACATION RENTAL LICENSE: VR-039 CLICK HERE to view photos on a mobile device. Additional …
  • Waterfront
  • Internet Access
  • Porch
  • Grill
  • Dishwasher
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(6)

Great views and convenient to the entire Keys chain

Left on Feb 09, 2011 for a stay in December 2010

Great location, fantastic views, great access to the Bay and atlantic. Older home but clean and well maintained. Nicely situated in the Keys for access to Key West to Key Largo. Home had only basic cable and the dish washer did not work but overall would recommend the home. If your looking for luxury, this is not your place but if you want to just experience the keys and all they offer it's …

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$429

5 BR / 4 BA / Sleeps 10

8 Reviews

$429

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140 Atlantic Lane

Islamorada house
5 BR / 4 BA / Sleeps 10 | Quick view
“ Excellent ” 8 Reviews

Details

Reviews

(8)

Amazing ocean views can be enjoyed from this beautiful stilt home with seperate mother-in-law cottage. You'll fall in love with this little piece of Heaven. Enjoy fishing, diving, and catching lobster with all the comforts of home. Best ocean views in town! Interior photos are available! Mile Marker 76.5, Oceanside. …
  • Waterfront
  • Ocean or water views
  • A/C or climate control
  • Grill
  • Dishwasher
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(8)

Summer vacation 2010

Left on Sep 13, 2010 for a stay in August 2010

Overall nice place, kitchen items were not very organized, and place could use a deep cleaning

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