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$70

2 BR / 2 BA / Sleeps 4

Bogey's Retreat - Florida Keys vacation rentals
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$70

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Bogey's Retreat

2 BR / 2 BA / Sleeps 4 | Quick view

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BOGEY'S RETREAT: Ideal for a golfer, it is located at Key West Golf Club. 2 pools nearby. $50 security deposit for Association gym card use. Stainless kitchen appliances, new beds and furnishings. HDTVs, DVD/Blu-Ray, Bose sound and WIFI.Rear bedroom looks at the golf course, front bedroom has French doors …
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Grill
  • Television
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$70

2 BR / 2 BA / Sleeps 6

2 Reviews

$70

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Wind Swept

2 BR / 2 BA / Sleeps 6 | Quick view
“ Very Good ” 2 Reviews

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Reviews

(2)

WIND SWEPT: Imagine yourself nestled within a serene, lushly landscaped picturesque community with walkways meandering around the only Caribbean golf course in the United States.This lovely 2 bedroom 1.5 bath townhome is freshly painted and newly furnished. Enter the open and airy living space which includes kitchen…
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Grill
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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(2)

Wind Swept

Left on Dec 12, 2013 for a stay in October 2013

The house was great Loved being on the golf course very quite area great pool Security was very nice and helpful The staff: At home was great Libby is the best

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$145

2 BR / 2 BA / Sleeps 6

11 Reviews

$145

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Ocean Pointe Two Bedroom Ocean Views

2 BR / 2 BA / Sleeps 6 | Quick view
“ Very Good ” 11 Reviews

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Reviews

(11)

Beautiful, newly remodeled 2 bedroom, 2 bathroom condo in sunny Tavernier Key (North Florida Keys), with a king bed in the master bedroom and 2 twin beds in the second bedroom, featuring flat screen TVs, a private balcony with chairs, cable TV, and complementary amenities. Ocean Pointe Suites at Key Largo is an all-…
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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Reviews

(11)

Typical Florida Keys experience

Left on Jan 01, 2014 for a stay in December 2013

The Florida Keys are laid back and most of the structures look like something out of a Popeye movie. Ocean Point Suites is no better and no worse than the competition. Finding the reservation desk is a bit confusing, but the receptionist was friendly and helpful.

We had two apartments, both pleasant enough, both with a view of the sea (and some swamp) and dozens of cats running around behind …

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$310

3 BR / 2 BA / Sleeps 7

17 Reviews

$310

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Duval Courtyard

3 BR / 2 BA / Sleeps 7 | Quick view
“ Excellent ” 17 Reviews

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Reviews

(17)

DUVAL COURTYARD - 3 bedroom 2 bath townhome has plenty of space, a fabulous location and all the amenities you could wish for. The main living area flows from kitchen to dining area to French doors that open to a balcony where you can sit and people watch. Master bedroom has bath ensuite along with its own balcony…
  • Shared outdoor pool (unheated)
  • A/C or climate control
  • Balcony or terrace
  • Parking
  • DVD Player
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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(17)

Christmas in Paradise

Left on Nov 06, 2008 for a stay in December 2006

A wonderful Christmas experience. No snow, no cold, just a relaxing time. Condo was roomy and aesthetically lovely. Loved the balcony overlooking the courtyard. Convenient location to everything in Old Town. Used the kitchen quite abit. Mini washer and dryer not great but a minor complaint. Would easily stay here again.

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$580

3 BR / 3 BA / Sleeps 6

Tucked away near the Southernmost Point, Louisa's Hideaway is it! - Florida Keys vacation rentals
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$580

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Tucked away near the Southernmost Point, Louisa's Hideaway is it!

3 BR / 3 BA / Sleeps 6 | Quick view

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Tucked away near the upper end of Duval Street you'll find this stylish, newly renovated three bedroom, three bath home. Thoughtful details are luxuriously appointed to suit the vacation guest looking for privacy and high design. Walk up the brick drive and enter the gate to the palm tree lined path that leads to …
  • Internet Access
  • A/C or climate control
  • Patio
  • Parking
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$270

2 BR / 1 BA / Sleeps 4

Pete's East Cottage: Cypress east cottage steps from Duval - Florida Keys vacation rentals
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$270

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Pete's East Cottage: Cypress east cottage steps from Duval

2 BR / 1 BA / Sleeps 4 | Quick view

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This property has it all! The styling of the original shot gun homes of Key West restored with a beautiful natural cypress exterior combines with the clean lines of a contemporary home. Each Twin opens to it's own semi-private deck and lounge area with steps into a large kidney shaped pool with waterfall. Inside the …
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Patio
  • Linens Provided
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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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

2 BR / 1 BA / Sleeps 4 | Quick view

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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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$750

4 BR / 4 BA / Sleeps 8

27 Reviews

$750

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Southard Street Queen Conch - A Historic compound with large sunny pool

4 BR / 4 BA / Sleeps 8 | Quick view
“ Excellent ” 27 Reviews

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Reviews

(27)

On a lovely tree-lined residential street in the heart of the historic Old Town district, this quiet, historic compound offers three separate vacation suites sharing a lush, large, sunny pool or combines for a wonderful four bedroom retreat. Downstairs enjoys a large, open floor plan with living and dining room, …
  • Internet Access
  • A/C or climate control
  • Deck
  • Parking
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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Reviews

(27)

What a lovely property

Left on Jun 18, 2009 for a stay in May 2008

This is a great home in a great location. All of the rooms are wonderfully furnished and clean. The backporch and sun deck are truly amazing and relaxing. I especially enjoyed the privacy of the pool and backyard for relaxing and resting. I would stay here again over and over again.

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$171

2 BR / 0 BA / Sleeps 6

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$171

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WI-27321

2 BR / Sleeps 6 | Quick view

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Brand new home with high end features just two canals from open water. Large seawall with dock posts, fish cleaning table and swim ladder. Upstairs relax or dine on huge screened deck overlooking canal with dining furniture and two lounge chairs. Two sets of double glass sliders lead into main inside area. Living …
  • Internet Access
  • Dishwasher
  • Microwave
  • Satellite or cable TV
  • Ceiling Fans
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$400

4 BR / 5 BA / Sleeps 8

2 Reviews

$400

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74920 Overseas Hwy

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

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Reviews

(2)

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

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Reviews

(2)

The Best

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

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

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$290

2 BR / 2 BA / Sleeps 6

9 Reviews

$290

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Beach Club #112 - Unique Oceanfront living

2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 9 Reviews

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Reviews

(9)

Unique oceanfront living only 65 feet from the Atlantic! The Key West Beach Club is a quiet, peaceful residential building that sits directly on the water. The breathtaking view can be seen as soon as you enter the unit. This comfortable 2 bedroom unit features a huge oceanfront balcony accessed from both the …
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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Reviews

(9)

Fabulous view

Left on Jun 19, 2009 for a stay in May 2009

This unit was just lovely, the view off the terrace was amazing. We had the pool (one of 2) to ourselves everyday. We never heard any of our neighbors. Although the beach was not manicured, the unit was very close to 2 beaches, if you want to sit in the sand.
We could see cruise ships and parasailing right off the pation. I can't say enough, it was GREAT.

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$66

1 BR / 1 BA / Sleeps 4

1 Reviews

$66

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Artist cottage with hot tub

1 BR / 1 BA / Sleeps 4 | Quick view
“ Poor ” 1 Reviews

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Reviews

(1)

The artist cottage is mainly used as a residence for visiting artist that are in town doing shows at my gallery. The cottage is very quiet and secluded with lots of privacy,situated amongst 100 year old trees and lush tropical foliage. The cottage was built in 1913 and is a true piece of old key west. The property is…
  • Hot Tub/Jacuzzi
  • Internet Access
  • Housekeeping Optional
  • Outdoor Dining Area
  • A/C or climate control
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Wonderful little cottage, not so wonderful owner

Left on Apr 07, 2014 for a stay in June 2013

First, let me say that I intended not to review this property simply because I didn't want to leave a negative review but today I got a letter in the mail that made me change my mind.The cottage was great, clean,neat,location great, and a great place for our little dogs, who were welcome. First there was no washing machine which didn't seem a problem because David assured us that our laundry …

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$100

2 BR / 3 BA / Sleeps 4

1 / 1

$100

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Executive Bay Club Unit G-5 - 28 NIGHT MINIMUM

2 BR / 3 BA / Sleeps 4 | Quick view

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Click here to view this photo slideshow on a mobile device.
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$367

2 BR / 2 BA / Sleeps 4

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$367

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Steam Plant - Luxurious 2/2 Condo w/ Amazing Views & Private Hot Tub

2 BR / 2 BA / Sleeps 4 | Quick view

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Key West regulars know that one of the best parts of downtown is actually a few blocks of the main street at the Historic Key West Seaport. The Seaport is a big part of the heart of Key West where dingy captains, commercial fisherman, sports anglers, pleasure seeking vessels, and those that admire it all come together…
  • Hot Tub/Jacuzzi
  • Internet Access
  • Balcony or terrace
  • Parking
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$1,000

5 BR / 4 BA / Sleeps 10

19 Reviews

$1,000

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DREAMING ON DUVAL- Luxury 5 Bed & Private Pool- As seen on HGTV House Hunters

5 BR / 4 BA / Sleeps 10 | Quick view
“ Excellent ” 19 Reviews

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Reviews

(19)

Luxury on Duval Street in historic Key West? Luxury is not what most people visiting Key West associate with Duval Street until you look at Dreaming On Duval! There are very few private homes on Duval, let alone a single family vacation rental that is steps away from everything Key West has to offer and accommodates …
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Deck
  • Parking
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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Reviews

(19)

Fabulous...

Left on May 24, 2010 for a stay in May 2010

Dreaming in Duval is a beautiful, spacious home. The home is very well equipt,and accomodated 10 people easily.
The location was perfect, we could walk to everything.
Dean and Paul were both great and very helpful.
One of our best vacations ever, we are already planning a return trip.

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$400

2 BR / 2 BA / Sleeps 8

1 / 6

$400

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Hyatt Sunset Harbor Key West, FL

2 BR / 2 BA / Sleeps 8 | Quick view

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Please note. This is a timeshare rental and I have only 1 week allotted to me. Please do not request any dates other than available week of March 8th through the 15th. This Hyatt property is a 2 floor--2 Bedroom Caribbean furnished condo type unit situated right in the heart of Key West facing the famous sunset. …
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Balcony or terrace
  • Parking
  • Grill
  • Suitable for children
  • Suitable for the elderly - elevator access
  • Wheelchair accessible - ask

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$467

5 BR / 5 BA / Sleeps 14

1 / 40

$467

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"SHARK KEY CHATEAU" Incredible 3-Story Mansion w/ Private Beach, Pool, & Spa

5 BR / 5 BA / Sleeps 14 | Quick view

Details

***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Shark Key Chateau is 'Grande' to say the least. With unspoiled views from every angle, to playful colors, and unrivaled decor and design, this home is a Chateau unlike any other. Shark Key Chateau is designed in true keys …
  • Private Beach
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$217

4 BR / 3 BA / Sleeps 12

1 Reviews

$217

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1108 Heron Rd - 28 Night Minimum

4 BR / 3 BA / Sleeps 12 | Quick view
“ Very Good ” 1 Reviews

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Reviews

(1)

Located in Key Largo at mile marker 95, oceanside, this pool home will really seal the deal. Just remodeled, and offering stunning Atlantic views, the home is ideal for a family seeking a combination of camaraderie and privacy. Divided into separate units on its two floors, each with its own kitchen, the home's decor …
  • Waterfront
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

We had a relaxing and complete vacation stay.

Left on Aug 05, 2013 for a stay in June 2013

The house was decorated and remodeled beautifully. The pool was a nice addition. All amenities were at the house.

I will be staying here again and again provided that it is available.

Brought my boat and there was ample space and area for fish cleaning, as well as, a couple of beers under the palms when done.

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$150

3 BR / 2 BA / Sleeps 6

1 / 1

$150

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127 Tequesta - 28 Night Minimum

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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$107

3 BR / 2 BA / Sleeps 8

1 / 11

$107

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Boaters Paradise in Ramrod Key

3 BR / 2 BA / Sleeps 8 | Quick view

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10 minutes to the OCEAN - DEEP WATER CANAL READY FOR LOBSTER SEASON!!!!! 3 bedroom 2 bath Stilt house on a canal. Nice screened in porch (mosquito proofed) to relax in the evening. 10 minutes to the Ocean!! Just 25 minutes to Key West. Walking distance to Looe Key Reef Resort and Tikki Bar or to Boondocks. 2 …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Pet friendly - ask
  • Suitable for children

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$600

4 BR / 0 BA / Sleeps 8

1 Reviews

$600

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76190 Overseas Highway - Casa Dorado

4 BR / Sleeps 8 | Quick view
“ Very Good ” 1 Reviews

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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 - ask
  • 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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$300

4 BR / 4 BA / Sleeps 10

8 Reviews

$300

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4 Bedroom with guest quarters! 612 Mariners Club

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

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Reviews

(8)

3-7 night minimum stay requirement varies by time of year. Three-story townhouse with over 2600 sq of living space...room for the whole family! Ground floor 1-bedroom (king bed) with kitchenette, open floor plan sitting area with queen sleeper sofa and a private full bath...perfect for grandma or the nanny. An …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(8)

A very comfortable place for a three generation holiday.

Left on May 29, 2012 for a stay in December 2011

The townhouse was good for all nine of us and we did not trip over each other. The kitchen was big enough for 3 or 4 to work in so meals got done in a hurry with several people helping. The swimming pool was great with its white sandy beach There were plenty of things to do close enough to keep us all happy. We had a great time and my expectations had been lower. So the only hitch was getting …

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$232

3 BR / 3 BA / Sleeps 6

1 / 21

$232

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Blackbeard's Treasure - MONTHLY Rental (30 night min.)

3 BR / 3 BA / Sleeps 6 | Quick view

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Save 3% off published rates if you pay by cash/check. To say this townhouse condominium is worth the amassed treasure of Blackbeard, one of the most notorious and wealthy pirates in seafaring history, is a major understatement. The 1950's era art deco Steamplant at water's edge has been quintessentially transformed …
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Suitable for the elderly - ask

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$600

3 BR / 3 BA / Sleeps 6

9 Reviews

$600

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Kemp House

3 BR / 3 BA / Sleeps 6 | Quick view
“ Excellent ” 9 Reviews

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Reviews

(9)

This Civil War Era home sits in Key West's most desirable Historic Seaport District, less than a block from the Gulf of Mexico. Did Abraham Lincoln sleep here? Probably not. But anyone staying today in this classic revival valued in the millions will find not only history but every creature comfort and contemporary …
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for the elderly - ask

Details

Reviews

(9)

very lovely

Left on Feb 09, 2009 for a stay in November 2008

Beautiful house. Near everything. Comfortable and well kept.

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$429

5 BR / 4 BA / Sleeps 10

8 Reviews

$429

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140 Atlantic Lane

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

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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. …
  • Ocean or water views
  • A/C or climate control
  • Grill
  • Dishwasher
  • Microwave
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children - ask
  • 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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$129

2 BR / 2 BA / Sleeps 4

2 Reviews

$129

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Moon Bay B-407

2 BR / 2 BA / Sleeps 4 | Quick view
“ Average ” 2 Reviews

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Reviews

(2)

A pleasantly decorated condo located at mm 104. This unit has 2 bedrooms and 1.5 bathrooms, plus its own deeded boat slip. This condo in conveniently located close to the main land, but far enough away from the mainland to enjoy a Keysy vacation. This is a perfect condo for fishermen, divers, or just a Key's getaway. …
  • Ocean or water views
  • Internet Access
  • A/C or climate control
  • Grill
  • Dishwasher
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

pics look nice

Left on Apr 05, 2013 for a stay in March 2013

If it wasn't for Freewheeler vacation rentals helping us out I would have requested a full refund. The unit was not cleaned, the mattresses were stained, the towels were insufficient and looked like they should be used for washing a floor not for personal use. To add to this the sheets have holes in them and the bedspreads have not been cleaned for a long time. On the good note there were no …

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$250

3 BR / 2 BA / Sleeps 10

1 Reviews

$250

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Key Largo Paradise!!!

3 BR / 2 BA / Sleeps 10 | Quick view
“ Excellent ” 1 Reviews

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Reviews

(1)

Beautiful 3 story 3 bedroom 2 baths home. Locate in key largo at MM 101 is on a canal which opens up to beautiful Tarpon Basin Bay with access to the Atlantic Ocean. Minutes from beautiful Penny Camp National Underwater Park. Close to local shopping, fine restaurants or just swimming with the dolphins! Come to the …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(1)

nice place

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

We enjoy staying at this place.

Very big place, very clean.

I got my deposit back.

I will visit again

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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

4 BR / 4 BA / Sleeps 8 | Quick view

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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
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$126

2 BR / 2 BA / Sleeps 4

8 Reviews

$126

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Ocean Pointe 5402

2 BR / 2 BA / Sleeps 4 | Quick view
“ Very Good ” 8 Reviews

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Reviews

(8)

Sweet little home away from home. This 2 bedroom 2 bath condo hosts beautiful views of the Atlantic Ocean. Sit on your back patio and watch over the marina or for those early risers watch an unforgettable sunrise from your 4th floor balcony. If you are looking to get out on the water the condo offers dockage.. or if …
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Washing Machine
  • A/C or climate control
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(8)

Lots of fun in the sun and great memories!

Left on Jul 22, 2010 for a stay in June 2010

The place was cute but the kitchen needs better cleaning all the cabinets were sticky and there was a roach in the pantry. But the view was grat and we loved the convinience of the dock.

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$250

2 BR / 2 BA / Sleeps 5

4 Reviews

$250

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Beautiful sunsets,Luxurious home on the bay

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

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Reviews

(4)

This is a brand new furnished vacation rental on the point with the best sunset views. Rates have been reduced during this introduction period. This home has 2 bedrooms and 1 and a 1/2 bath. It has a 700 sq ft addition of kitchen and family room with direct views of the sunset. New leather furniture and two bedroom …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(4)

Convenient for large families

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

We spent a very nice long weekend at this house. It is very comfortable for large families, and the living room area is great for children. The open kitchen space is very convenient for cooking lovers and the house is fully equipped. The owner was very helpful. I would only complain about cleanliness. It was not the cleanest house I have ever seen. Otherwise I loved it!

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$299

4 BR / 4 BA / Sleeps 10

9 Reviews

$299

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Exquisite 4 bedroom, 4 bath! 607 Mariners Club

4 BR / 4 BA / Sleeps 10 | Quick view
“ Excellent ” 9 Reviews

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Reviews

(9)

3-7 night minimum stay requirement varies by time of year. Three-story townhouse with over 2600 sq of living space...room for the whole family! Ground floor 1-bedroom (king bed) with kitchenette, open floor plan sitting area with queen sleeper sofa and a private full bath...perfect for nana or the kids! An interior …
  • Waterfront
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(9)

vacation

Left on Apr 06, 2012 for a stay in March 2012

Everything was wonderful. My only complaint was the downstairs apartment didn't even have a coffee table and the bedroom floor was full of "dust bunnies". Other than that the resort was beautiful and the condo was great.

Thank you for all your help with the rental. Debbie and annie were just terrific.

Lee Okon

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$185

3 BR / 3 BA / Sleeps 6

1 Reviews

$185

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Moon Bay Condo, Boat Slip & Aw-Inspiring Sunsets

3 BR / 3 BA / Sleeps 6 | Quick view
“ Very Good ” 1 Reviews

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Reviews

(1)

Welcome to your home away from home! “Bel Cielo” is a beautiful two-story condo in the quaint community of Moon Bay, located at mile marker 104 in Key Largo. (Moon Bay was recently featured on HGTV's Beach Front Bargain Hunt!) Featuring 1,146 square feet of living space with handsome furnishings, Bel Cielo is not …
  • Waterfront
  • Ocean or water views
  • Sauna
  • Internet Access
  • Washing Machine
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(1)

Great Place

Left on Aug 11, 2014 for a stay in August 2014

Bel Cielo is nicely furnished and well maintained. An abundance of bath and beach towels is included and the kitchen is fully equipped. The owner responded promptly to questions we had about the property during the booking process and when we stayed there. The grounds throughout the Moon Bay condo complex are well maintained and it is conveniently located directly on the Overseas Highway. …

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$250

2 BR / 2 BA / Sleeps 6

34 Reviews

$250

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Duval Square

2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 34 Reviews

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Reviews

(34)

The rooftop community of Duval Square is a prime perch from which to launch the best tropical vacation ever. The townhomes cluster on the second story above their namesake square. Winding pathways bordered by swaying palm and colorful plantings arranged in terracotta pots define the layout. Best of all, the small …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Suitable for the elderly - ask

Details

Reviews

(34)

Barbecue

Left on Aug 14, 2008 for a stay in February 2008

The vacation week was good, except for the use of the barbecue. When we had stayed there before we had used the barbecue every other night (and gone out for dinner the other nights). We have a 6 yr. old and the deal we made with him was the above (as you know 6 yr. olds couldn't care less about eating out) and prefer barbecues and staying in. (ours does anyway). This February we were told that we…

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$929

4 BR / 4 BA / Sleeps 10

13 Reviews

$929

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75731 Overseas Highway

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

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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 - ask
  • 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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$299

3 BR / 3 BA / Sleeps 8

7 Reviews

$299

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Opulence in an island setting ~ 809 Mariners Club

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

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Reviews

(7)

Distinctive and luxury living is redefined in this exceptional, 2600 sq ft. two-story townhouse. Even as you approach the threshold it becomes immediately apparent this is not your ordinary vacation accommodation. The custom entry door leads invitingly into the foyer lighted with dazzling crystal sconces which …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(7)

Excellent!

Left on Nov 19, 2013 for a stay in November 2013

Beautiful condo and exceptionally clean. Everything seemed new in the unit. Check in was easy and not for from the property. Only thing the condo lacked was a wine cork... :)

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$450

3 BR / 2 BA / Sleeps 6

8 Reviews

$450

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3 Bedroom Oceanfront Condo Key West

3 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 8 Reviews

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Reviews

(8)

Large 3 Bedroom, 2 Bath OCEANFRONT condo. Breathtaking views of the Atlantic from every room. Tropical landscaped property with large heated pool and Jacuzzi. Just steps to Smathers Beach which has swimming, jet skis, parasailing, etc. Fully appointed condo with all the amenities of home at your fingertips. Sorry …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Suitable for children

Details

Reviews

(8)

Beautiful oceanfront condo

Left on Jan 11, 2014 for a stay in January 2014

We just rented this unit - it was wonderful!!! Beautiful kitchen,
recently remolded. Large family room. Bedrooms nice sizes. Unit
has a complete wrap around deck with ocean views. About 3 minute walk to Smathers beach. Really nice pool & 15 person hot tub. If you are
a beach person this unit is for you!! Only negative - not that close
to the down town area(5 minute car ride) - however unit …

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$275

3 BR / 3 BA / Sleeps 7

1 / 22

$275

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Exciting marina-front living! 113 Mariners Club

3 BR / 3 BA / Sleeps 7 | Quick view

Details

Pristine villa overlooking world-class marina... The excitement of marina-front living can be found right here at Mariners Club Key Largo. Overlooking the marina waterfront in this upscale gated community lies Villa 113. This unique, ground floor location was designed to accentuate the experience of dockside life …
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

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$215

1 BR / 1 BA / Sleeps 2

10 Reviews

$215

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Campbell Suite

1 BR / 1 BA / Sleeps 2 | Quick view
“ Excellent ” 10 Reviews

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Reviews

(10)

Having spent a long weekend in this one bedroom, one and a half bath apartment, one previous guest described it as a "cozy condo hideaway in the heart of historic Key West." The historic significance is close to home. It starts with the white stucco building that houses this suite and other vacation condos. The three-…
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control

Details

Reviews

(10)

The best condo!

Left on Dec 15, 2011 for a stay in November 2011

The condo was as cute as can be. Decorated beautifully, clean, and in a perfect location. It was a great vacation.

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$77

2 BR / 2 BA / Sleeps 4

1 / 14

$77

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THE PALMS 402

2 BR / 2 BA / Sleeps 4 | Quick view

Details

Minimum Rental: 1 Month Pure pleasure will be yours in this beautifully remodeled and immaculate condo. You'll love the uncluttered and modern décor along with the recent renovations. Enjoy the picturesque views of Alligator Reef and the Atlantic Ocean from this 4th floor balcony. Watch the fishing boats …
  • 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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$217

3 BR / 2 BA / Sleeps 6

1 Reviews

$217

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MY PARADISE

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

Details

Reviews

(1)

Minimum Rental: 1 Month Oceanfront - Beach - Protected Dock and located in the Fishing Capital of the World - Islamorada. Realize your dreams - a beach home located on a swimmable beach and a place to dock your boat. This home is indeed a rare find in The Florida Keys. From the moment you arrive, you'll know …
  • Ocean or water views
  • Internet Access
  • Balcony or terrace
  • Parking
  • Grill
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(1)

My Paradise from architect's perspective

Left on Jan 23, 2013 for a stay in April 2012

My wife and I spend a month at My Paradise and, as an architect, there are certain aspects that bear mention. First, if the weather is mild, you can open the wall of folding glass doors and unite the main interior room (dining, den and kitchen) with the oversize teak deck. The deck itself is a marvel. A covered sitting area gets you out of the sun, with six teak sun loungers for warming up and …

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$167

2 BR / 2 BA / Sleeps 4

1 / 24

$167

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OCEAN HARBOUR K4

2 BR / 2 BA / Sleeps 4 | Quick view

Details

Minimum Rental: 1 Month New on the rental market. This is your opportunity to secure your winter getaway at a luxurious oceanfront condo in one of Islamorada's most prestigious condominium communities. Ocean front dockage is available for boats up to 28' in length (separate rental); heated free-form swimming pool, …
  • 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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$132

3 BR / 2 BA / Sleeps 6

1 / 24

$132

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BAYSIDE BREEZE

3 BR / 2 BA / Sleeps 6 | Quick view

Details

MINIMUM STAY: 30 DAYS NEW HOME (2013) Spend the fall or winter in the Florida Keys! You will love this wonderful 2013 built stilt home. Features include an open living area with gourmet kitchen, stainless steel appliances, including a wine refrigerator and granite counters. The oversized center island in …
  • Internet Access
  • Balcony or terrace
  • Parking
  • Grill
  • Refrigerator
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$67

2 BR / 2 BA / Sleeps 6

1 / 16

$67

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BOATER'S DELIGHT

2 BR / 2 BA / Sleeps 6 | Quick view

Details

Minimum Rental: 1 Year Beautifully furnished, this almost new single family stilt home sits on an ocean side canal front lot. Bring your boat and your swim suit! This 2 bedroom, 2 bath home has everything you need, including a laundry room with a clothes washer and dryer and a fully equipped kitchen. Enjoy your …
  • Hot Tub/Jacuzzi
  • Patio
  • Parking
  • Grill
  • Refrigerator
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$240

4 BR / 3 BA / Sleeps 10

1 / 20

$240

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EMERALD COVE

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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$110

2 BR / 2 BA / Sleeps 4

1 / 20

$110

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BEACON REEF 314

2 BR / 2 BA / Sleeps 4 | Quick view

Details

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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$165

1 BR / 2 BA / Sleeps 4

1 / 17

$165

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LARGO KAI - GROUND LEVEL

1 BR / 2 BA / Sleeps 4 | Quick view

Details

MINIMUM STAY: 1 MONTH Only 1 - 4 people? Want something spacious but don't need a mansion? This is it!! Rent only the ground level portion of this magnificent home. This home offers gorgeous ocean views, private boat basin and a covered tiki with a hammock. You will quickly transform into 'island time' when…
  • Patio
  • Fitness Room
  • Parking
  • Grill
  • Refrigerator
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$150

2 BR / 2 BA / Sleeps 4

1 / 25

$150

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BEBA'S REEF HOUSE

2 BR / 2 BA / Sleeps 4 | Quick view

Details

Minimum Stay 1 Month. "Beba's Reef House" will capture your imagination the moment you enter the home and rise to the main living level through the reef painted on the walls of the stair well and the photos of fish captured by the owner during numerous dives here in the Keys. This is a charming 2 bedroom, 2 bath home …
  • Internet Access
  • Balcony or terrace
  • Parking
  • Grill
  • Satellite or cable TV
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$283

4 BR / 3 BA / Sleeps 10

1 Reviews

$283

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CONCH BAR SOUTH

4 BR / 3 BA / Sleeps 10 | Quick view
“ Very Good ” 1 Reviews

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Reviews

(1)

MINIMUM STAY: 29 DAYS NEW RENTAL OPPORTUNITY! This magnificent home is located at the mouth of a wide canal in Plantation Key and offers phenomenal open water views. The furnishings are new and provide a comfortable and extremely inviting living environment. This 4 bedroom 3 bath single family home (3/2 up; 1/1…
  • Shared outdoor pool (unheated)
  • Internet Access
  • Balcony or terrace
  • Parking
  • Grill
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(1)

Great property but poor experience with realtor

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

We rented for the month of November with 9 people in our party. The property and home are beautiful but we unfortunately did not have a very good experience withKeys Holiday rental department. One of the main reasons we rented the house was the use of the boat davits but two weeks before our arrival I was informed the davits were being removed. I was left with no choice but to buy additional …

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$300

3 BR / 3 BA / Sleeps 6

5 Reviews

$300

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Indigo Reef Villa 54

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

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Reviews

(5)

This spacious three bedroom, two and a half bath Villa will make you feel right at home. Each bedroom has it’s own television, with a 60” flat screen TV in the living room. The Villa has direct sunset views looking out to the Gulf of Mexico, which can be enjoyed from the porch or upper balcony. The kitchen…
  • Central heating
  • Balcony or terrace
  • Fitness Room
  • Books
  • Linens Provided
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(5)

Paradise in the Fl Keys

Left on Mar 13, 2014 for a stay in February 2014

We had an amazing stay at Indigo Reef Resort. The unit was beautiful, clean and well maintained! We had a total of 4 adults in our party and we all had plenty of room in the townhome. We really enjoyed spending time on the deck watching the breathtaking sunsets. The location was perfect for our party and we had lots to do in the area. Thanks again John!

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$135

2 BR / 1 BA / Sleeps 4

1 Reviews

$135

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MOON BAY A410

2 BR / 1 BA / Sleeps 4 | Quick view
“ Very Good ” 1 Reviews

Details

Reviews

(1)

MINIMUM STAY: 7 NIGHTS. This 4th floor end unit in one of Key Largo's finest bay front condominium complexes offers a beautiful view of the Florida Bay and lots of natural light. You'll love the updated kitchen with granite counters, new cabinetry and appliances. New linens and fresh paint add to the desirability…
  • Shared outdoor pool (unheated)
  • Internet Access
  • Parking
  • Grill
  • Refrigerator
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(1)

Great winter getaway!

Left on Mar 20, 2014 for a stay in January 2014

We had a wonderful 2 month stay at Moon Bay. The condo was very comfortable and in a great location. We thoroughly enjoyed relaxing by the pool and sitting out on the bay. No problems at all. The Key Holiday staff made check-in and check-out very easy. Hope to be able to return some time in the future.

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