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$358

2 BR / 2 BA / Sleeps 6

1 Reviews

$358

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LITTLE BAY - Cottage

Islamorada villa – 12.5 mi away
2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

Minimum Rental: 7 Nights Cottage - This is one of three rental units on this property. The cottage is a ground level dwelling separate from two duplex units. It offers a unique floor plan with the main living area in the center of the house with kitchen, dining area, sitting area and a full bath. To the right is …
  • Ocean or water views
  • Internet Access
  • Parking
  • Grill
  • Refrigerator
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(1)

A place where memories are made.....

Left on May 28, 2013 for a stay in May 2013

The pictures really don't do this place justice, there are so many comforts that it feels more like a home. It is in a great location and since it is gated, it was safe enough for my 9 year old twins to go exploring on their own. It truly has something for everyone. We cooked, laid out, watched the sunset, even took a dip in the bay. It was really lovely. We will definitely be returning.

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$133

2 BR / 2 BA / Sleeps 4

BEACON REEF 211 - Long Key vacation rentals
1 / 18

$133

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BEACON REEF 211

Islamorada condo – 12.7 mi away
2 BR / 2 BA / Sleeps 4 | Quick view

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Minimum Rental: 1 Month This is a very special unit in a premier condominium complex located directly on the Atlantic Ocean and in the heart of Islamorada. This unit provides spectacular ocean views. It is one of the few units that offer spiral stairs to the ground level directly from your private balcony. The …
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • Patio
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$215

3 BR / 2 BA / Sleeps 6

17 Reviews

$215

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Conch Key: Private Single Family Fishing Compound

Conch Key house – 7.1 mi away
3 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 17 Reviews

Details

Reviews

(17)

LOW SUMMER AND FALL RATES $1500.-1600. PER WEEK including taxes and cleaning. It is a well kept secret that the best time for staying in the Keys is the Summer and Fall. Moderate temperatures- very warm sea waters- no waiting time at restaurants- Traffic, even in Key West is way down. We are a licensed 3 bedroom…
  • Waterfront
  • Ocean or water views
  • Wireless Internet
  • Housekeeping Optional
  • Washing Machine
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible - ask

Details

Reviews

(17)

Gorgeous home!

Left on Sep 27, 2010 for a stay in August 2010

What a gorgeous home! The owner was so accommodating when planning the trip. The home felt like a 5 star hotel.
Beautiful and still felt like home. Great location too!

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$167

3 BR / 2 BA / Sleeps 6

1 Reviews

$167

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108 West Plaza Del Sol - 28 Night Minimum

Long Key house
3 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 1 Reviews

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Reviews

(1)

Cozy, canalfront pool home at MM 74 in Islamorada's desirable Port Antigua (Lower Matecumbe Key) with quick Florida Bay access and a short ride to the Atlantic Ocean. The bed rooms are located in a separated, quiet part of the house, while the living, dining, and kitchen are open for enjoying each other's company. …
  • Waterfront
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Perfect!!!

Left on Aug 06, 2013 for a stay in July 2013

We spent a month at this house with the family. The location was perfect - especially if you have a boat. (If you do not, there are several companies nearby that will deliver one to you). Regardless, it's worth every dime just to sit on the balcony and watch the tarpon and manatees frolic in the waterway out back.

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$400

4 BR / 3 BA / Sleeps 10

Ocean Front Split Level Keys House **HURRY! Major last minute discounts in April & May!** - Long Key vacation rentals
1 / 29

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Beautiful four bedroom, Ocean Front home with private beach in sunny Islamorada (near Key Largo). Welcome to our little slice of paradise in the Florida Keys! Come and relax at our beautiful ocean front home with breathtaking, panoramic views of the Atlantic ocean. This spit level home is located in Islamorada; the …
  • Private Beach
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$295

2 BR / 2 BA / Sleeps 6

Call today to book for Memorial Day - Long Key vacation rentals
1 / 20

$295

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Call today to book for Memorial Day

Duck Key villa – 8.7 mi away
2 BR / 2 BA / Sleeps 6 | Quick view

Details

Fully renovated Hawks Cay Spa Villa with 2 bedrooms and 2.5 Bathrooms. The Villa has new furniture, stainless steel appliances, flat screen TV's and new wood floors. Come and relax in the accommodations our Villa has to offer. The Villa has an open room concept with the Kitchen open to the Living Room which opens to …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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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 – 3.3 mi away
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 …
  • 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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$715

4 BR / 3 BA / Sleeps 10

1 / 38

$715

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82754 Overseas Highway

Islamorada house – 12.1 mi away
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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$380

3 BR / 3 BA / Sleeps 6

3 Reviews

$380

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75333 Overseas Hwy

Matecumbe Key house – 4.9 mi away
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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$929

4 BR / 4 BA / Sleeps 10

13 Reviews

$929

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75731 Overseas Highway

Matecumbe Key house – 5.3 mi away
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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$183

4 BR / 3 BA / Sleeps 10

1 / 20

$183

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EMERALD COVE

Islamorada house – 3.3 mi away
4 BR / 3 BA / Sleeps 10 | Quick view

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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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$472

3 BR / 3 BA / Sleeps 6

1 Reviews

$472

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Maison Matecumbe 304

Islamorada condo – 10.3 mi away
3 BR / 3 BA / Sleeps 6 | Quick view
“ Excellent ” 1 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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$70

2 BR / 2 BA / Sleeps 6

1 / 16

$70

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THE PALMS 301

Islamorada condo – 12.5 mi away
2 BR / 2 BA / Sleeps 6 | Quick view

Details

Minimum Rental: 1 Month This exceptional condo has been impeccably maintained and is located in one of the finest condo complexes in Islamorada. It features an updated kitchen, remodeled baths and is comfortably furnished. This unit is ready for your arrival. Be sure to look at the Visual Tour to see just how …
  • 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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$70

2 BR / 2 BA / Sleeps 4

1 / 18

$70

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THE PALMS 214

Islamorada condo – 12.5 mi away
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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$358

2 BR / 2 BA / Sleeps 6

3 Reviews

$358

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LITTLE BAY - Upper Duplex

Islamorada villa – 12.5 mi away
2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 3 Reviews

Details

Reviews

(3)

Minimum Rental: 7 Nights Upper 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. This is one of 3 separate units for rent by the week or month. Each unit sleeps up to 6 people - …
  • Ocean or water views
  • Internet Access
  • Patio
  • Parking
  • Grill
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(3)

Iguanas, sunshine and the sea in your backyard.......

Left on Nov 05, 2012 for a stay in October 2012

We found Little Bay after our previously planned accomodation had been damaged in a fire so Andi & Katy at Keys Holiday Rentals literally saved us from camping on the beach! The apartment couldn't have been nicer, 2 bed, 2 bath with the second bedroom having twin beds so was perfect for the children (6 & 12). The apartment was well laid out with a HUGE deck overlooking the garden (iguanas!) and …

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$358

2 BR / 2 BA / Sleeps 6

4 Reviews

$358

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LITTLE BAY - Lower Duplex

Islamorada villa – 12.5 mi away
2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 4 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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$200

2 BR / 1 BA / Sleeps 4

2 Reviews

$200

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83261 Old Highway

Islamorada house – 12.8 mi away
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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$358

4 BR / 3 BA / Sleeps 8

4 Reviews

$358

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76004 Overseas Highway

Islamorada house – 5.6 mi away
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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$314

3 BR / 2 BA / Sleeps 6

6 Reviews

$314

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La Casa Habana: Beautiful 3 BR on Gulf w Pool

Grassy Key house – 11.9 mi away
3 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 6 Reviews

Details

Reviews

(6)

La Casa Habana is a 3 bedroom , 2 bath house overlooking the Gulf of Mexico on exclusive and private Morton St. on Grassy Key. This house has been extremely popular for over 10 years. It has everything you need for a great vacation-bikes, kayaks, snorkel gear, fishing gear, Cable TV and wifi internet for those rare …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Housekeeping Optional
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(6)

Great Vacation Home

Left on Mar 12, 2012 for a stay in March 2012

This is a beautifully decorated and comfortable house. It is clean, neat and well organized. The kitchen is well stocked for cooking anything. Everything is well maintained and we got everything we needed. The pool is really nice, and its heated. The hot tub is terrific. The views of the Gulf, especially at sunset ,or the early morning, are magical. This is a great spot for a getaway or a …

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$63

1 BR / 2 BA / Sleeps 4

1 Reviews

$63

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THE PALMS 417

Islamorada condo – 12.5 mi away
1 BR / 2 BA / Sleeps 4 | Quick view
“ Excellent ” 1 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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$286

3 BR / 3 BA / Sleeps 6

11 Reviews

$286

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Bay Harbour Complex

Long Key condo
3 BR / 3 BA / Sleeps 6 | Quick view
“ Excellent ” 11 Reviews

Details

Reviews

(11)

Please send us an inquiry or call us for availability. Prices vary on the units. Bay Harbour Condominiums, built in 2003, is a beautiful area with great condos located in Islamorada, mile marker 74, bay-side. Exterior amenities include deep-water boat slips in a protected harbor, lush tropical landscaping, …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Suitable for children
  • Suitable for the elderly - elevator access
  • Wheelchair accessible - ask

Details

Reviews

(11)

Excellent. Very nice unit

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

We thorough enjoyed our stat in this unit. It was spotless, had a nice view, and very convenient. We would definitely ask for the same unit next time.

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$429

3 BR / 3 BA / Sleeps 8

8 Reviews

$429

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Villa Pamela - Tropical Paradise

Grassy Key house – 11.5 mi away
3 BR / 3 BA / Sleeps 8 | Quick view
“ Excellent ” 8 Reviews

Details

Reviews

(8)

3 bedroom 'suites" villa on the Gulf of Mexico on exclusive and private Morton Street on beautiful Grassy Key, next to Marathon, the "heart of the Keys". Each private suite has its own bathroom-completely renovated in the fall of 2010, its own seating area and flatscreen TV. Beautifully landscaped grounds with private…
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(8)

Can not wait to go back!

Left on Feb 08, 2011 for a stay in November 2010

I stayed at Villa Pamela over 4 months ago and I still think about this vacation. The home was perfect, it had every ammenity you could ask for. The kitchen was stocked with everything you could possibly need, the outdoor areas provided plenty of entertainment and seating. The heated pool was great. Fishing of the dock was a blast. I would definitely rent this unit again.

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$333

3 BR / 3 BA / Sleeps 6

5 Reviews

$333

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Open water in Florida Keys with beautiful sunsets

Duck Key house – 9.4 mi away
3 BR / 3 BA / Sleeps 6 | Quick view
“ Excellent ” 5 Reviews

Details

Reviews

(5)

Private residence on Duck Key. 2 bedrooms and 2 baths upstairs with a seperate one bedroom one bath apartment downstairs. Apartment has own kitchen and family room. Private dock with heated pool. Ocean kayak and fishing rods included. Catch tarpon right off the dock. House extensively landscaped for total …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(5)

The best vacation ever

Left on Oct 31, 2010 for a stay in August 2010

This home is the perfect place to vacation. It has all the amenities you could ask for. Beautiful kitchens, comfortable living areas and wonderful sleeping accomodations. My children and I could not have asked for more. We spent our days swimming in the ocean and relaxing by the pool. The fishing was outstanding. We caught several large tarpon, sharks and baracudda. There are lights under the …

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$400

3 BR / 3 BA / Sleeps 5

6 Reviews

$400

Book

You will never want to leave

Matecumbe Key house – 3.5 mi away
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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$615

5 BR / 6 BA / Sleeps 10

1 Reviews

$615

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OCEAN FRONT VILLA: Great Heron House

Marathon villa – 7.6 mi away
5 BR / 6 BA / Sleeps 10 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

Great Heron House Ocean Front - Estate Luxury in ever detail and design with spectacular ocean views throughout. Private pool and spa. Spacious 5 bedroom 5.5 bath sleeps up to 10 guests. Sister property to the Grand Mangrove. Both accommodations reflect a meticulous attention to detail. Granite Countertops, Wolf and …
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(1)

Sunshine and Luxury

Left on Mar 12, 2014 for a stay in January 2014

We spent a wonderful week at the Great Heron House in January, 2014. It was an extended family vacation so there were four adults, one toddler, and one infant. The accommodations were perfect. A room, with en suite bathrooms, for everyone, a gourmet kitchen fully equipped, very cozy and comfortable living space with fantastic views of the water, and fantastic outdoor space including a gas …

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$215

2 BR / 2 BA / Sleeps 4

16 Reviews

$215

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132 Columbus Drive

Islamorada house – 6.2 mi away
2 BR / 2 BA / Sleeps 4 | Quick view
“ Excellent ” 16 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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$77

2 BR / 2 BA / Sleeps 4

1 / 22

$77

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SUNSET HAMMOCK 4B

Tavernier condo – 12.6 mi away
2 BR / 2 BA / Sleeps 4 | Quick view

Details

LONG TERM RENTAL Available 4-15-2015 - Completely Furnished. 12 months preferred will consider 6+ months. Luxurious 2 bedroom, 2 bath townhome in gated bayfront complex with pool, hot tub, and tennis courts. This wonderful townhome is nestled in a tropical hardwood hammock. Enjoy your time in the Keys in this …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • Balcony or terrace
  • Parking
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$329

3 BR / 3 BA / Sleeps 6

7 Reviews

$329

Inquire

137 Leserra Lane

Islamorada house – 6.0 mi away
3 BR / 3 BA / Sleeps 6 | Quick view
“ Excellent ” 7 Reviews

Details

Reviews

(7)

Beautiful designer appointed Oceanside canal home located at the Mile Marker 76.5 in Lower Matecumbe (South part of Islamorada). This home is the second one in on a point and has a great ocean view. Fully loaded kitchen with dishwasher, microwave, coffee maker, toaster, and blender. There are two flat panel TV's in …
  • 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

(7)

We had a very relaxing and fun-filled vacation

Left on Jul 15, 2010 for a stay in June 2010

The house is in a great location in Lower Matecumbe. Robbie's restaurant is only one mile away which we went to three times (twice by car, once by boat). We also went to anne's Beach twice with our dogs. The house is great for pets, the yard is fenced in and there is plenty of room for the dogs to run around.

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$225

4 BR / 3 BA / Sleeps 9

1 Reviews

$225

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Bliss in the Florida Keys

Long Key house
4 BR / 3 BA / Sleeps 9 | Quick view
“ Excellent ” 1 Reviews

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Reviews

(1)

Beautiful canal front, clean, home located on ocean side in Long Key. MM 68. 4 bedrooms 3 baths total: 3 bedroom, 2 bath upstairs, 1 bedroom/bath (studio) downstairs. Great fishing and diving moments away. This is our family's vacation hideaway. Never rented prior to December 2012. Direct TV w HBO, Regional Sports …
  • Waterfront
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(1)

Must stay! Gorgeous house with plenty of room.

Left on Jun 14, 2014 for a stay in June 2014

Currently staying here and couldn't be happier. Comfortably sleeping 9 people in our party (4 adults, 4 kids/teens and a baby). The kitchen is stocked very well. Gorgeous view of the ocean from the upper deck. Quiet neighborhood. Will definitely be back!

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$1,715

10 BR / 10 BA / Sleeps 20

13 Reviews

$1,715

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Alligator Reef Luxury Estate

Islamorada house – 14.2 mi away
10 BR / 10 BA / Sleeps 20 | Quick view
“ Excellent ” 13 Reviews

Details

Reviews

(13)

Got a large group that wants to "get away from it all"? Or do you need lots of space for a family reunion or wedding? This is the perfect solution! Terrific location, beautiful view, two private pools for you to enjoy... And since it's 4 separate homes, you aren't right on top of each other. Wide decks let you enjoy …
  • 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

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Reviews

(13)

Island Perfection

Left on Jul 01, 2010 for a stay in May 2010

Perfect house for a island getaway. Hammocks, wildlife, marinelife, pool, kayaks, near "the infamous islamorada sandbar", ping pong table, boat rentals nearby, the place couldn't be better for kicking back soaking up everything that makes the Florida Keys special.

Real friendly and easy to deal with reservation systems and staff. A++ all the way. We will use Freewheeler again and again.

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$286

3 BR / 2 BA / Sleeps 6

6 Reviews

$286

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76300 Overseas Highway

Islamorada house – 5.9 mi away
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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$500

4 BR / 3 BA / Sleeps 8

9 Reviews

$500

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Private Beachfront Paradise

Matecumbe Key house – 8.5 mi away
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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$77

2 BR / 2 BA / Sleeps 5

1 Reviews

$77

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THE PALMS 314

Islamorada condo – 12.5 mi away
2 BR / 2 BA / Sleeps 5 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

Minimum Rental: 1 Month Sensational oceanfront views are yours from both the master bedroom and the balcony of this beautifully appointed condo. Watch the fishing charter boats as they come and go from Bud and Mary's Marina. You'll be able to see cruise ships as they pass by Alligator Reef and Light House or …
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • Patio
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(1)

Wow, what a beautiful view

Left on Feb 13, 2015 for a stay in January 2015

This condo was clean, nicely furnished and had a view to die for. We really appreciated the washer and dryer in the unit, which most did not have. Also, being on the end we had "the window" in the master bedroom and in the daytime the view would take your breath. However, at night the lights from the parking lot would shine into our bedroom. Alas, with the flip of a switch an outside shutter …

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$125

0 BR / 1 BA / Sleeps 2

2 Reviews

$125

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Duplex with 2 Efficiencies located 50 yards from ocean $750 -$875/week, Unit 9

Grassy Key condo – 10.8 mi away
0 BR / 1 BA / Sleeps 2 | Quick view
“ Excellent ” 2 Reviews

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Reviews

(2)

Two charming efficiencies located 50 yards from the Atlantic Ocean. Both are fully furnished with well-equipped kitchens and are decorated with a Caribbean flair. In the private front yard, each unit has a gas-BBQ grill, a picnic table with large umbrella's for shade. Unit 9 has two single beds which can be …
  • Internet Access
  • Clothes Dryer
  • A/C or climate control
  • Patio
  • Parking
  • Suitable for the elderly

Details

Reviews

(2)

Quaint sweet little place

Left on Jun 12, 2014 for a stay in January 2014

We stayed for one week in January. We loved our one room efficiency with its beautiful art work and nice decor. The neighbors were great, the sunsets were awesome, the small private beach was delightful. We would love to come back again. The only thing we would add would be a small love seat. We had to bring in lawn chairs to watch tv. Other the that....we were happy campers. Thanks Hans

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$110

2 BR / 2 BA / Sleeps 4

1 / 20

$110

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BEACON REEF 314

Islamorada condo – 12.7 mi away
2 BR / 2 BA / Sleeps 4 | Quick view

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Minimum Rental: 1 Month Beacon Reef is one of the most desirable condominium complexes in the Upper Keys. Located in Islamorada it is convenient to everything - restaurants, fishing, diving, snorkeling, swim with the dolphin programs and much more. Picture yourself relaxing on your own private balcony …
  • 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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$175

3 BR / 3 BA / Sleeps 8

1 Reviews

$175

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BLUE WATER RETREAT

Islamorada house – 5.9 mi away
3 BR / 3 BA / Sleeps 8 | Quick view
“ Excellent ” 1 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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$83

2 BR / 2 BA / Sleeps 4

1 / 19

$83

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135 Gulfview Dr - 28 Night Minimum!!!!

Islamorada house – 4.0 mi away
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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$429

5 BR / 4 BA / Sleeps 10

8 Reviews

$429

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140 Atlantic Lane

Islamorada house – 6.0 mi away
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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$110

2 BR / 1 BA / Sleeps 4

1 / 17

$110

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75651 Overseas Hwy Islamorada Fla Keys Oceanfront

Matecumbe Key condo – 5.3 mi away
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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$123

3 BR / 2 BA / Sleeps 6

1 / 21

$123

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THE PALMS 316

Islamorada condo – 12.5 mi away
3 BR / 2 BA / Sleeps 6 | Quick view

Details

MINIMUM STAY: 29 DAYS Enjoy unobstructed and panoramic views of the Atlantic Ocean from your own private balcony! This 3 bedroom/2 bath condo unit features direct ocean views from the living room, balcony and two of the three bedrooms. Tropical furnishings create a warm and inviting atmosphere. You'll really…
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • Balcony or terrace
  • Fitness Room
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$63

2 BR / 2 BA / Sleeps 4

1 / 15

$63

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THE PALMS 506

Islamorada condo – 9.5 mi away
2 BR / 2 BA / Sleeps 4 | Quick view

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Description….. MINIMUM STAY: Minimum Rental: 1 Month 5th Floor unit at one of Islamorada's favorite condo complexes. This unit was recently sold and the new owners are beginning to update some of the dĂ©cor. You'll love the fantastic panoramic ocean views as you relax or dine on the balcony. There's …
  • 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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$107

2 BR / 2 BA / Sleeps 4

1 / 23

$107

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BEACON REEF 501

Islamorada condo – 12.7 mi away
2 BR / 2 BA / Sleeps 4 | Quick view

Details

MINIMUM STAY: ONE MONTH. Exceptional 5th floor (top floor) 2 bedroom 2 bath condo at Beacon Reef. Ocean views from the open air balcony. You'll be so glad you have chosen to spend your holiday here. The kitchen was remodeled in 2013 - granite counters, stainless steel appliances, and tray ceiling with …
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fitness Room
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$358

4 BR / 3 BA / Sleeps 8

1 / 12

$358

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Blue Harbour

Islamorada house – 14.7 mi away
4 BR / 3 BA / Sleeps 8 | Quick view

Details

Village Permit #VR-09-82 You can not rent this property for less than one week. Ahhhh...Ocean Front....Protected Dockage... Blue Harbor is located at Mile Marker 85, in beautiful Islamorada. This Ocean Front four bedroom,three bath home will sleep 8 people very comfortably. (One of the bedrooms is on the ground level…
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$599

3 BR / 2 BA / Sleeps 8

1 / 12

$599

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5004 Hawks Cay 3 BR / 3 BA Private Pool Duck Key

Duck Key villa – 8.8 mi away
3 BR / 2 BA / Sleeps 8 | Quick view

Details

This Villa is located within the Village at Hawks Cay on Sunset Village Drive. Enjoy Tranquil Settings in this 3 Bedroom / 3 Bath Villa with your own private pool just off the back deck. The Master Bedroom has a King Bed. The second bedroom has two queen beds and the third bedroom has one queen bed. Enjoy, …
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • A/C or climate control
  • Central heating
  • Suitable for children
  • Suitable for the elderly - ask

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$329

2 BR / 2 BA / Sleeps 6

15 Reviews

$329

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Gerry's Florida House

Marathon house – 12.3 mi away
2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 15 Reviews

Details

Reviews

(15)

RELAX Get away from the outside world at this lovely hide-away that includes two bedrooms, two bathrooms and a pull-out-sofa. There's a panoramic view of the Gulf of Mexico from every room in the house. We've made an effort to provide the things that will make your stay comfortable, fun and enjoyable. You'll love our …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(15)

just another day in paradise.

Left on Apr 07, 2011 for a stay in May 2010

You want for nothing in this house. peaceful, relaxing, fun, lots to do. the porch is the best place in the house, we never sit inside, you just want to spend the day enjoying the view. It's close to great places to eat and entertainment. We drive into Key West for the day only an hour away. We fish off the dock and snorkle. The beds are very comfortable. enjoy hot afternoons in the pool and …

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$243

1 BR / 1 BA / Sleeps 2

13 Reviews

$243

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Conch Key TreeTop Cottage with 23' Sailboat

Conch Key cottage – 7.1 mi away
1 BR / 1 BA / Sleeps 2 | Quick view
“ Excellent ” 13 Reviews

Details

Reviews

(13)

This one bedroom, one bath cottage is located high in the swaying coconut trees overlooking the water. The living room area has sliding glass doors that open onto a small deck area with a water view. The bedroom is tastefully furnished with an antique double bedroom set and the entire cottage is decorated in "Keys-…
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for the elderly - ask

Details

Reviews

(13)

Your very own sailboat and cottage on the water with sunset views in the fabulous Florida Keys!

Left on Dec 04, 2012 for a stay in November 2012

As a frequent visitor to the Florida Keys, this has been one of the best hideaways that we have discovered and love to come back to. It is rare to find such a nicely maintained sailboat dedicated to you along with your accommodations.

Conch Key is a unique fishing village on an charming island in the heart of the Florida Keys. Marathon is just 10 miles away where you'll find a multitude of …

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$147

2 BR / 2 BA / Sleeps 4

1 / 17

$147

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BEACON REEF 222

Islamorada condo – 12.7 mi away
2 BR / 2 BA / Sleeps 4 | Quick view

Details

Minimum Rental: 1 Month Extraordinary ocean front condo with panoramic views of the Atlantic Ocean. Relax on your own balcony or use the spiral stairs to access the sandy beach below. This condo is located in one of the most prestigious condo complexes in Islamorada. It offers 2 spacious bedrooms, 2 full baths…
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • Patio
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$600

4 BR / 3 BA / Sleeps 8

1 Reviews

$600

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Latitude

Islamorada house – 5.1 mi away
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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$1,279

5 BR / 7 BA / Sleeps 10

1 / 13

$1,279

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Kara-Pan

Islamorada house – 10.7 mi away
5 BR / 7 BA / Sleeps 10 | Quick view

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You can not rent this property for less than one week. The ultimate island experience awaits you at Kara-Pan I. This exquisite, private, two story, Plantation Style home is located on a pristine natural white sand beach with oceanviews that inspire relaxation. The 5 bedroom 7 bath home with a wrap around porch, is …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Housekeeping Optional
  • Suitable for children
  • Suitable for the elderly

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$208

2 BR / 2 BA / Sleeps 4

2 Reviews

$208

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75130 Overseas Highway

Matecumbe Key house – 4.8 mi away
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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