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$99

2 BR / 2 BA / Sleeps 8

3 Reviews

$99

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

Islamorada condo
2 BR / 2 BA / Sleeps 8 | Quick view
Excellent3 Reviews

Details

Reviews

(3)

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

(3)

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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$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
Excellent7 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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$149

1 BR / 1 BA / Sleeps 3

3 Reviews

$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…

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$215

3 BR / 2 BA / Sleeps 7

3 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
Very Good3 Reviews

Details

Reviews

(3)

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

(3)

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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$133

3 BR / 2 BA / Sleeps 7

TURTLE TIME - Islamorada vacation rentals
1 / 16

$133

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TURTLE TIME

Islamorada house
3 BR / 2 BA / Sleeps 7 | Quick view

Details

Minimum Rental: 1 Month Charming vacation home located in the beautiful neighborhood of Port Antigua. You will love this home! There is a wonderful open concept floor plan with 3 nicely proportioned bedrooms. Sliding doors open from the dining area into the sunroom overlooking the canal. You'll find this …
  • Internet Access
  • Balcony or terrace
  • Parking
  • Grill
  • Refrigerator
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$63

1 BR / 2 BA / Sleeps 4

1 Reviews

$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 …

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$100

2 BR / 1 BA / Sleeps 4

1 / 1

$100

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241 Tollgate Blvd - 28 NIGHT MINIMUM!!!!!!!!!!!!!!

Islamorada house
2 BR / 1 BA / Sleeps 4 | Quick view

Details

"Cute & Keysy" perfectly describe this Conch home! Located in the Tollgate Shores subdivision of Lower Matecumbe (south Islamorada), this delightfully quaint home has lots of character, charm, and is well-maintained. You'll enjoy sea breezes and the smell of salty air coming through the windows of the sunroom, or …
  • 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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$358

4 BR / 3 BA / Sleeps 8

4 Reviews

$358

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76004 Overseas Highway

Islamorada house
4 BR / 3 BA / Sleeps 8 | Quick view
Excellent4 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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$800

4 BR / 4 BA / Sleeps 8

2 Reviews

$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 …

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$929

4 BR / 4 BA / Sleeps 10

13 Reviews

$929

Inquire

75731 Overseas Highway

Matecumbe Key house
4 BR / 4 BA / Sleeps 10 | Quick view
Excellent13 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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$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
Excellent3 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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$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
Excellent1 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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$179

2 BR / 2 BA / Sleeps 6

4 Reviews

$179

Inquire

BROCK HAUS ON THE GULF

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

Details

Reviews

(4)

Minimum Rental: 7 Nights (Saturday to Saturday) BROCKHAUS ON THE GULF is an end unit townhouse on the water's edge with water views on 3 sides! The main living area faces the Florida Bay, one side faces the inlet leading to the marina basin and the back faces the marina. The panoramic open water views from this unit …
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Internet Access
  • Balcony or terrace
  • Parking
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(4)

Great week on Islamorada

Left on Aug 21, 2013 for a stay in August 2013

Just returned from a week at Brockhaus. This was our 4th time staying at this property (although the last time was in 2009) and everything felt very familiar and comfortable. The location is perfect,the views are spectacular, and the convenience of the boat slip right out the door is a huge plus! The 2 bedrooms are comfortable but the town home could use a bit of updating (it hasn't changed a bit…

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$135

1 BR / 1 BA / Sleeps 2

1 / 18

$135

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Hippie Home

Islamorada house
1 BR / 1 BA / Sleeps 2 | Quick view

Details

The Hippie Home was Built with Love in the Sunshine of the Spirit. Nestled in Islamorada, the Sportfishing Capital of the World. The Neighborhood is Quiet and Pet Friendly with a Private Beach and Tiki Hut. Close to Restaurants, Shopping, Recreation, Fishing Charters, Scuba Diving, and Snorkeling. Across the Street …
  • A/C or climate control
  • Balcony or terrace
  • Parking
  • Grill
  • Linens Provided

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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 Good2 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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$358

2 BR / 2 BA / Sleeps 6

4 Reviews

$358

Inquire

LITTLE BAY - Lower Duplex

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

Details

Reviews

(4)

Minimum Rental: 7 Nights Lower Duplex - This is one of three rental units on this fabulous property. The Little Bay property is a one acre lush tropical setting in a gated compound located directly on Florida Bay. The units are available for rent by the week, or month. Each unit sleeps up to 6 people - rent …
  • Ocean or water views
  • Internet Access
  • Patio
  • Parking
  • Grill
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(4)

Paradise!

Left on Jun 03, 2013 for a stay in May 2013

My family and I spent Memorial Day Weekend at this gorgeous property and it was like paradise! Not only was it beautiful inside and out it had a sophisticated charm and inviting ora from the moment you entered the property and opened the door! This place screams class while still giving you the feeling of total relaxation. The beds are amazing!!! The grounds are clean and beautiful and we even …

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$215

2 BR / 2 BA / Sleeps 4

16 Reviews

$215

Inquire

132 Columbus Drive

Islamorada house
2 BR / 2 BA / Sleeps 4 | Quick view
Excellent16 Reviews

Details

Reviews

(16)

This is a neat house! It sits right on the ocean with a large yard (by keys standards!). Very nicely landscaped (hibiscus, palm trees, tall pine trees, green grass)with statues from all over the world. Very private with a big gate. The house is decorated with pictures taken from all over the world and different keys …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(16)

Exactly what we were looking for

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

We were looking for a waterfront rental to give us more room than a reg hotel or bungalow. We were not looking for a pool and wanted something laid back. This was exactly what we were looking for and suited us, a fmily of 4 to the proverbial T. Not for a larger group/family or for folks looking for "Island Luxe".

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$208

2 BR / 2 BA / Sleeps 4

2 Reviews

$208

Inquire

75130 Overseas Highway

Matecumbe Key house
2 BR / 2 BA / Sleeps 4 | Quick view
Excellent2 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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$67

2 BR / 2 BA / Sleeps 4

1 / 14

$67

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THE PALMS 408

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

Details

Minimum Rental: 1 Month Comfortably furnished and ready for you. Conveniently located just steps from a full service marina and 2 highly acclaimed restaurants. Watch the sun rise over the ocean as fishing boats leave on their daily charters, or watch the spectacular sunsets over the bay. Exercise in the men's or…
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Patio
  • Fitness Room
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$663

5 BR / 6 BA / Sleeps 10

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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$472

4 BR / 3 BA / Sleeps 8

9 Reviews

$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 …

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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
Excellent4 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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$190

2 BR / 0 BA / Sleeps 4

1 Reviews

$190

Inquire

Futura Condos and Townhomes

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

Details

Reviews

(1)

Please send us an inquiry or call us for availability. We have condos and townhomes. Prices vary on the units. Your own tropical paradise overlooking the fabulous Florida Bay in Islamorada. Futura Yacht Club is a 70 unit community with a 53 slip marina and accommodations available for that tranquil tropical …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Most awesome vacation in Islamorda Florida!!

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

Futura - The price is right. The location is perfect. The townhouse is very comfortable, beautifuly decorated, with a most awesome view of Florida Bay. The marina, dock, and boat ramp are all at the same location and are well maintained. The pool, tennis courts, basketball, and volley ball court are an added bonus.
In addition, Freewheeler Realty has been providing our vacation services for over …

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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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$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
Excellent6 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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$150

3 BR / 2 BA / Sleeps 6

1 / 1

$150

Inquire

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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$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
Excellent6 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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$243

2 BR / 3 BA / Sleeps 6

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

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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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$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
Excellent1 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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$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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$175

3 BR / 3 BA / Sleeps 8

1 Reviews

$175

Inquire

BLUE WATER RETREAT

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

Details

Reviews

(1)

Minimum Rental: 1 Month Location, location, location! This home has it all - ocean side Lower Matecumbe location, totally remodeled in 2009. Relax by the cocktail pool or sunbathe in the private roof top sunning area. There are blue water ocean views from almost every room in this home. It is located on a canal …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Patio
  • Parking
  • Grill
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(1)

Blue Water = Everything that you want

Left on Jul 15, 2013 for a stay in July 2013

This place delivers.

You never really know what you are going to get from looking at a website and photos. I just stayed there July/2013 and this place is great, everything is new and clean. Most of all the house is on a peninsula that looks at the ocean from all sides and is just a few miles south of most of that main attractions in Islamorada giving the home a calm but close feel. Also working…

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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
Excellent1 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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$200

2 BR / 2 BA / Sleeps 10

1 / 11

$200

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Executive Bay Condo Islamorada Florida Keys

Islamorada condo
2 BR / 2 BA / Sleeps 10 | Quick view

Details

Make yourself at home in your own private paradise in the Fabulous Florida Keys! The exclusive Executive Bay Club is a gated community with 24 hour security situated waterfront on the Florida Bay in Islamorada, just an hour from the hussle and bustle of Miami, yet a world away. Enjoy five-star amenities such as a …
  • Wireless Internet
  • A/C or climate control
  • Central heating
  • Parking
  • Grill

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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
Excellent3 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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$183

4 BR / 3 BA / Sleeps 10

1 / 20

$183

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EMERALD COVE

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

Details

MINIMUM RENTAL: 28 NIGHTS (ONE MONTH) You'll love watching the fabulous sunsets over the tranquil waters in this semi-private lagoon setting. This is a three story single family home and offers two balconies overlooking the water and dock area. There's room to dock one 30' boat and a fish cleaning station conveniently…
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Balcony or terrace
  • Parking
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$70

2 BR / 2 BA / Sleeps 4

1 / 18

$70

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THE PALMS 214

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

Details

Minimum Rental: 1 Month Gorgeous 2 bedroom, 2 bath condo. This is a gated complex located directly on the Atlantic Ocean. This unit has unobstructed views of the ocean from the master suite and the balcony. Wake up every morning, open the curtains and view a panorama of the Atlantic Ocean directly in front of you…
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • Balcony or terrace
  • Suitable for children - ask
  • Suitable for the elderly - ask

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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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$472

3 BR / 3 BA / Sleeps 6

1 Reviews

$472

Inquire

Maison Matecumbe 304

Islamorada condo
3 BR / 3 BA / Sleeps 6 | Quick view
Excellent1 Reviews

Details

Reviews

(1)

This three bedroom, three bathroom condominium sits on a lushly landscaped property, offering the Florida Keys you've always imagined. Enjoy beautiful oceanfront vistas from one of two balconies. Take a dip in the spacious pool that sits right at the foot of the condo staircase. Or journey a few yards further to the …
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Porch
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Relaxing in Islamorada

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

Everything was beautiful. Very nice property. Private but very close to fishing charters.

Toaster did not work and upstairs a/C quit working the night before we left. Other than that the condo was great.

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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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$133

3 BR / 2 BA / Sleeps 6

1 Reviews

$133

Inquire

MATECUMBE JEWEL

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

Details

Reviews

(1)

Minimum Rental: 1 Month You will love jewel of a home! Located in Lower Matecumbe, this charming canal front home offers a swimming pool, dockage, direct access to the ocean, covered fish cleaning station, a screened lanai, inviting décor and comfortable accommodations. It is located on a dead-end street in a …
  • Internet Access
  • Patio
  • Parking
  • Grill
  • Refrigerator
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(1)

Our Lobster Trip to the Keys

Left on Aug 24, 2013 for a stay in August 2013

My family and I stayed at the Matecumbe Jewel in the month of august for Lobster season. The home shows even better than the photos, was clean, well furnished and kept. We could not have asked for better accomodations while on our first Lobstering vacation! The service by Keys Holiday Rental was a+++! We will certainly be back! Thanks again to everyone at Keys Rental and the owners of the …

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$600

4 BR / 4 BA / Sleeps 8

1 Reviews

$600

Inquire

76190 Overseas Highway - Casa Dorado

Islamorada house
4 BR / 4 BA / Sleeps 8 | Quick view
Very Good1 Reviews

Details

Reviews

(1)

Casa Dorado is a premier rental vacation home on Lower Matecumbe Key in Islamorada, Florida. Completely renovated in 2014, the spacious living and dining areas, four bedrooms, and three and a half bathrooms will make for a very comfortable stay during your visit to the Florida Keys. The house is located on the Florida…
  • 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

Details

Reviews

(1)

Casa Dorado delivers!

Left on Dec 26, 2014 for a stay in December 2014

The house is newly remodeled and in great condition. Very clean- which was a must for me! The views are wonderful. We thouroghly enjoyed the week we spent there (myself, my husband, our 24yr old daughter and her friend). It was a great location for biking, walking, kayaking and paddle boarding. The home has a pool, but we did not use it because it was not heated. We highly recommend Casa Dorado.

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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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$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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$715

3 BR / 4 BA / Sleeps 6

1 Reviews

$715

Inquire

The Palms

Islamorada house
3 BR / 4 BA / Sleeps 6 | Quick view
Average1 Reviews

Details

Reviews

(1)

VR-203 You can not rent this property for less than one week. Relax and rejuvenate at The Palms. Features are a plantation-style home and beautiful wrap around porch, 3 bedrooms/3.5 baths, a beach entry pool, and abundant coquina decking. The natural landscaping enhances the amazing grounds and ocean blue pool. Also …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Pretty nice place....the pool was a bummer.

Left on Apr 08, 2013 for a stay in March 2013

The site was beautiful. Nice sized house, clean, beautiful view, well kept grounds. Really nice covered porch all around the house where you could get out of the sun and enjoy the views and palm trees. There are houses on either side, but privacy was maintained.

The big let down was the pool. We rented the house exclusively for our kids to have free run of a private pool....but discovered …

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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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$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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$500

4 BR / 3 BA / Sleeps 8

4 Reviews

$500

Inquire

241 Bougainvillea St

Islamorada house
4 BR / 3 BA / Sleeps 8 | Quick view
Excellent4 Reviews

Details

Reviews

(4)

This home is located in a nice, quiet family neighborhood at the 90 mile marker (90 miles from Key West), Bayside. The house sits on the last canal of the neighborhood...very short boat ride to the bay (only a minute or so). Deep water dockage - 65' of dock space. There is an downstairs fully equipped bedroom/Game …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • A/C or climate control
  • Porch
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(4)

wonderful home, great vacation, will be back!

Left on Feb 10, 2011 for a stay in December 2010

This was a beautiful home. Will rent here again. This was our 8th year of vacationing in the Keys, and this house and it's location was the best yet!

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$643

4 BR / 3 BA / Sleeps 8

1 Reviews

$643

Inquire

Aguazul

Islamorada house
4 BR / 3 BA / Sleeps 8 | Quick view
Very Good1 Reviews

Details

Reviews

(1)

Village Permit #VR-09-82 You can not rent this property for less than one week. Ahhhh...Ocean Front...Pool...Dockage...It's all hear at Aguazul. Aguazul is located at Mile Marker 89, in beautiful Islamorada. This gorgeous four bedroom,three bath home will sleep 8 people very comfortably. Aguazul has everything you …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(1)

The perfect getaway

Left on Sep 26, 2011 for a stay in August 2011

My family had a fantastic vacation. This home is located really close to some great restaurants. It was so nice to sit back and relax all day while the kids played in the ocean and pool.

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