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$180

3 BR / 3 BA / Sleeps 6

FAN-tastic Getaway - Florida Keys vacation rentals
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$180

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FAN-tastic Getaway

3 BR / 3 BA / Sleeps 6 | Quick view

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FAN-tastic GETAWAY: Formerly owned by actress and fan dancer, Sally Rand.60" Smart TV and surround sound in living room; Dade County pine walls, wine cellar and every conceivable culinary tool in kitchen.1st floor master suite with Smart TV, WIFI, and bathroom ensuite with indoor shower and outdoor private shower…
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Grill
  • Television
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$150

3 BR / 3 BA / Sleeps 8

1 Reviews

$150

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Fisherman's Dream - Ocean Front House with Dock

3 BR / 3 BA / Sleeps 8 | Quick view
“ Very Good ” 1 Reviews

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Reviews

(1)

Welcome to our slice of paradise! Come and relax at our beautiful 3-bedroom home in the Florida Keys. Our home is located in Tavernier, the Sport Fishing Capital of the World. It is a private, gated home directly on the water with a small pier & fishing/boat dock. Our two-story home has master bedroom with a king bed …
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Right on the water

Left on Nov 23, 2014 for a stay in July 2014

This property is very comfortable. Clean and well kept. I loved sitting outside overlooking the waterway. You can even bring your boat!

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$400

4 BR / 3 BA / Sleeps 12

Ocean Front Split Level Keys House - Florida Keys vacation rentals
1 / 29

$400

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Ocean Front Split Level Keys House

4 BR / 3 BA / Sleeps 12 | Quick view

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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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$127

2 BR / 2 BA / Sleeps 4

2 Reviews

$127

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Angela Cottage: A hideaway in Old Town

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

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Reviews

(2)

30 DAY MINIMUM RENTAL This cute cottage just off of Frances Street is a great hideaway, still in Old Town, but a good central location to get to the Historic seaport or new town. The light & airy combined living/dining area with its soft color toned furnishings, hardwood floors & many windows create a relaxing Key …
  • Internet Access
  • A/C or climate control
  • Deck
  • Grill
  • Linens Provided
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

Outstanding

Left on Jun 26, 2009 for a stay in March 2009

I have rented the Angla Cottage for the past three seasons. The house is very comfortable with space for guests in a separate portion of thje house. Swimming pool is great, and outdoor dining area is outstanding for any meal. The kitchen is new and all the necessary pots and pans are present.

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$133

3 BR / 2 BA / Sleeps 6

1 / 25

$133

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"SEMINARY ST HIDEAWAY" 3 Bd 2 Bth Home w/ Private Pool

3 BR / 2 BA / Sleeps 6 | Quick view

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***Due to licensing restrictions, this home requires a minimum stay of 28 nights*** This newly renovated 3 bedroom "home away from home" sits right smack in the middle of the Key West island and is a short distance to everywhere you will want to go during your vacation! Located on Seminary St, in a quiet …
  • Internet Access
  • A/C or climate control
  • Grill
  • Linens Provided
  • Satellite or cable TV
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$1,048

6 BR / 6 BA / Sleeps 22

1 / 33

$1,048

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"PAPA'S HIDEAWAY - NIGHTLY GROUP UNIT" Guesthouse - Sleeps up to 22!

6 BR / 6 BA / Sleeps 22 | Quick view

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Papa's Hideaway is a Guesthouse property comprised of Garden of Eden , Torrents of Spring , Sun Also Rises , For Whom the Bell Tolls , Islands in the Stream Minimum Stay: Please contact Key West Vacation Rentals regarding minimum stays and special rates. Minimum stay requirements apply on weekends (at least…
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Fitness Room
  • Grill
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$70

2 BR / 2 BA / Sleeps 6

1 / 32

$70

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A Little Slice of Paradise

2 BR / 2 BA / Sleeps 6 | Quick view

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A LITTLE SLICE OF PARADISE (monthly rental): Secluded community, steps from the golf course, minutes from the beach, airport and some of the locals' favorite restaurants. 2 bedrooms, 1 full bath upstairs; open floor plan downstairs with sleeper sofa for guests, half bath, and screened porch. WIFI, HDTVs, fully-…
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Television
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$275

2 BR / 2 BA / Sleeps 6

1 / 15

$275

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Keys Waterfront Vista

2 BR / 2 BA / Sleeps 6 | Quick view

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Waterfront 2 bedroom stilt home with 2 full baths with tubs, large great room, fully stocked kitchen, cable, wifi, interenet, washer/ dryer, central a/c. `house is located on a clean, swimmable deepwater flow through canal with a 60 ft cement dock. Ladder for easy exit. Property large enough to handle a boat and …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly - ask

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$83

1 BR / 1 BA / Sleeps 6

1 / 17

$83

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Providence Suite - Monthly Rental

1 BR / 1 BA / Sleeps 6 | Quick view

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***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Nestled in tropical, flowering gardens, the Providence Suite is perfectly located, 1/2 block from Duval Street Downstairs is the living room with Queen sleeper sofa, dining room and fully equipped kitchen. Outdoor table and…
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Deck
  • Fitness Room
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$100

2 BR / 2 BA / Sleeps 4

2 Reviews

$100

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157 Ojibway Ave - 28 NIGHT MINIMUM

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

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Reviews

(2)

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

Details

Reviews

(2)

Very nice and relaxing...

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

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

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$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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$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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$350

3 BR / 3 BA / Sleeps 8

2 Reviews

$350

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Bay Harbour Waterfront Condo

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

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Reviews

(2)

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

Details

Reviews

(2)

Great Vacation!

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

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

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$208

2 BR / 2 BA / Sleeps 4

2 Reviews

$208

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75130 Overseas Highway

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

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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
  • Smoking allowed - ask
  • Suitable for children - ask
  • 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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$150

3 BR / 3 BA / Sleeps 8

1 / 25

$150

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Higgs Beach Hacienda - 3 Bed 2.5 Bath Monthly Rental Near Beach. Huge Yard!

3 BR / 3 BA / Sleeps 8 | Quick view

Details

Tucked into a quiet residential neighborhood, this renovated home is the perfect getaway for a family or group of friends looking to experience the Key West island life! This 3 bedroom home is on Patricia St, just a block from the scenic biking bath that runs along the Atlantic side of the island; very close (less …
  • Internet Access
  • A/C or climate control
  • Linens Provided
  • Dishwasher
  • Microwave
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$598

4 BR / 5 BA / Sleeps 10

1 / 35

$598

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"SIMONTON COURT COTTAGES" 4 Units in 1! Sleeps up to 10 Only 1 Block To Duval

4 BR / 5 BA / Sleeps 10 | Quick view

Details

"Simonton Court Cottages" consists of the 4 nightly units "Audubon House," "Truman Efficiency," "Monroe Efficiency," and "Mallory Efficiency." In total, this group rental sleeps 8 - 10 comfortably. Perfect for cost-conscious, larger, groups who are looking for great a location. Take advantage of this fantastic …
  • A/C or climate control
  • Microwave
  • Refrigerator
  • Toaster
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$117

2 BR / 2 BA / Sleeps 6

1 / 17

$117

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Amazing Grace

2 BR / 2 BA / Sleeps 6 | Quick view

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***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Amazing Grace is nestled in the middle of the island on Seidenberg Avenue that dead ends into Salt Run Canal that divides Key West in half. With 2 bedrooms, 2 bathrooms, off street parking and a hot tub you may find that you …
  • Dishwasher
  • Microwave
  • Refrigerator
  • Toaster
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$838

6 BR / 5 BA / Sleeps 16

1 / 25

$838

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ESCAPE 2 PARADISE - 2 Beautiful 3-Story Homes w/ Pvt Pools. Steps From Duval

6 BR / 5 BA / Sleeps 16 | Quick view

Details

Located in the luxury townhome complex "Echo Gardens," "Escape 2 Paradise" consists of two homes, units #3 and #4 - A Key Escape and Absolutely Paradise - which are right next door to each other. Equipped with two private pools, two private parking spaces, and enough room to sleep 16 people, "Escape 2 Paradise" truly…
  • Internet Access
  • A/C or climate control
  • Patio
  • Grill
  • Stereo or CD player
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$167

2 BR / 2 BA / Sleeps 6

8 Reviews

$167

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"CASA 625" Monthly Rental w/ Private Pool. Beautiful Interior

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

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Reviews

(8)

***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** The superb location at the top of Solares Hill, three blocks to the Historic Seaport and Duval Street, one block to the Public Library; Casa 625 will amaze you with the detailing, decorating and attention to detail! Sit on the …
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Fitness Room
  • Grill
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(8)

Always love 625

Left on Jan 27, 2011 for a stay in November 2010

This is a nice property I have stayed at multiple times. If it were my house, I would enhance it by making the master suite upstairs private (not wide open to the rest of the house) and I would put a TV in the master that's a reasonablt size (there was a 17" or so TV in a beautiful MBR!). Put the small TV downstairs in the BR there and get a new flatscreen that fits the property and the MBR.

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$200

2 BR / 2 BA / Sleeps 4

1 / 12

$200

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30 night Minimum Stay Heart of Historic downtown 2 bedroom 2 1/2 Bathroom

2 BR / 2 BA / Sleeps 4 | Quick view

Details

This unit offers the perfect way to visit Key West, park your car and walk everywhere. Sunset celebration is only steps away. This town home is complete luxury with viking appliances, custom kitchen cabinets, granite counter tops, beautifully furnished, and Westin Hotel heavenly beds. The amenities include one …
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Linens Provided
  • Dishwasher
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$167

3 BR / 3 BA / Sleeps 6

4 Reviews

$167

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"TOBAGO GRANDE" Monthly Rental Home w/ Private Pool Just 1 Block To Duval

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

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Reviews

(4)

***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Tobago House is just steps from restaurants, night life, Hemingway's House, and the 'Southernmost Point' of the United States. This home offers an open, airy floor plan with old style pine walls and floors, cathedral ceilings …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Patio
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(4)

Perfect in Every Way!

Left on Nov 14, 2013 for a stay in October 2013

I stayed at Tobago house for the month of October and loved it! This was my 2nd stay - my best friend rented the house for 6 weeks in the spring of 2012 - and it was even better than I remembered. The house is well appointed with all the things one needs to set up house for a few days or for several weeks.

The location is prime and provides easy access to Duval street and all the shops and …

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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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$329

3 BR / 3 BA / Sleeps 6

6 Reviews

$329

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138 Bayview Isle

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

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Reviews

(6)

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

Details

Reviews

(6)

Perfect location

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

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

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$100

1 BR / 1 BA / Sleeps 4

1 / 9

$100

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VO-122

1 BR / 1 BA / Sleeps 4 | Quick view

Details

This clean and very well maintained canal front vaction home features 1Bd/1Ba with master bedroom king size bed with access to the full size bathroom. Living room features a futon sleeper with 32' flat screen television with DVD player. 35'concrete seawall features dock posts, cleats, swim ladder.ships.concrete …
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask

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    $388

    2 BR / 3 BA / Sleeps 6

    1 / 34

    $388

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    "HAVANA HIDEAWAY" - Beautiful Home w/ Pvt Pool Just Steps To Duval

    2 BR / 3 BA / Sleeps 6 | Quick view

    Details

    The Beach Boys on one of their many trips to Key West (they are Mojito buds with Jimmy Buffett) stayed at our vacation rental called Havana Hideaway, where they wrote the song Kokomo - according to a very reliable source at the Pink Cab Company. This vacation rental is a modern two-story, built in the best conch …
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

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    $227

    3 BR / 3 BA / Sleeps 6

    2 Reviews

    $227

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    "VILLA AZUL" Luxurious Monthly Home w/ Pvt Pool, Deck & Gorgeous Interior.

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

    Details

    Reviews

    (2)

    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** You will certainly enjoy this wonderful historic home with recent renovations, perfectly placed pool, and plenty of outdoor living space located at 1116 Curry Lane. This home is situated in the heart of Old Town, just 4 blocks …
    • Internet Access
    • A/C or climate control
    • Deck
    • Fitness Room
    • Grill
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (2)

    Beautiful and comfortable home

    Left on Jan 27, 2011 for a stay in December 2008

    Villa azul is a wonderfully decorated and appointed home in the historic Old Town section of Key West. The home and grounds were beautiful, serene, private and cozy. It is hard to imagine that this property would not exceed anyone's expectations.

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    $378

    3 BR / 3 BA / Sleeps 8

    6 Reviews

    $378

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    "ALMOST SOUTHERNMOST TOO" - Private Pool - Half Block To Duval St! Sleeps 8

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

    Details

    Reviews

    (6)

    Part of ALMOST SOUTHERNMOST RETREAT Almost Southernmost Too in the 400 block of Truman Avenue is the perfect location, located between Duval Street and Whitehead St. Just around the corner from Hemingway's House and the Historic Lighthouse Museum, Almost Southernmost Too is a perfect example of shotgun architecture …
    • Internet Access
    • A/C or climate control
    • Balcony or terrace
    • Fitness Room
    • Grill
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (6)

    Fantastic, wonderful experience.

    Left on Nov 23, 2011 for a stay in November 2011

    Great location, in the center of KeyWest. Parked the car and walked,biked,trollied everywhere. Beautiful color scheme, every room was vibrant with a South Florida palat. Fantastic new kitchen and pool. Spent many hours on the pool patio with a 6-toe cat from the Hemmingway house. Just an all around wonderful experience. We will return to this house again in 2013...Thanks for making this a …

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    $429

    5 BR / 4 BA / Sleeps 10

    8 Reviews

    $429

    Inquire

    140 Atlantic Lane

    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. …
    • 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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    $183

    2 BR / 2 BA / Sleeps 6

    1 / 20

    $183

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    A Low Key Paradise

    2 BR / 2 BA / Sleeps 6 | Quick view

    Details

    Located on a quiet residential street in the beautiful Key West neighborhood of Casa Marina, A Low Key Paradise has a beautiful open layout, with views of the large private patio and pool visible as soon as you enter. Guests can walk to nearby Higgs beach, and Higgs beach dog park— perfect for your family member …
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Outdoor Dining Area
    • A/C or climate control
    • Pet friendly
    • Suitable for children
    • Suitable for the elderly
    • Wheelchair accessible - ask

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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

    Details

    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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    $1,184

    12 BR / 8 BA / Sleeps 30

    2 Reviews

    $1,184

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    Twelve Bedrooms! Up to 30 peoplePools-Docks-Kayaks

    12 BR / 8 BA / Sleeps 30 | Quick view
    “ Excellent ” 2 Reviews

    Details

    Reviews

    (2)

    WHAT IS UNIQUE ABOUT THIS VACATION RENTAL? This rental offers a great option for multi-family vacationing by providing three 4-bedroom homes side-by-side. This gives you 3 kitchens, 3 pools, 3 deep water docks, 3 gas grills, parking for 8 vehicles and 6 kayaks! These properties are non-smoking and two of the three …
    • Waterfront
    • Ocean or water views
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Pet friendly
    • Suitable for children
    • Suitable for the elderly

    Details

    Reviews

    (2)

    50th Wedding anniversary Celebration

    Left on Dec 29, 2013 for a stay in June 2013

    27 of us rented 3 houses(Gulf Shore Suites)in Marathon for my parents' 50th wedding anniversary. We really enjoyed the waterfront property with the option to swim in the ocean or pools. We loved the kayaks and outdoor dining with grills, too. The docks were wonderful for fishing in your own backyard; we enjoyed several dinners that were freshly caught! The houses were roomy and afforded us plenty…

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    $190

    3 BR / 3 BA / Sleeps 6

    1 Reviews

    $190

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    "CLUB CLARK" Gorgeous 3 Bd 3 Bth Home w/ Pvt Pool. Close to Dante's!

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

    Details

    Reviews

    (1)

    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** The main dwelling includes a beautiful, newly-renovated kitchen, a master bedroom with en-suite, a second bedroom with twin beds (which can be made into a king upon request), a full guest bathroom including a tub and full …
    • Internet Access
    • A/C or climate control
    • Patio
    • Grill
    • Linens Provided
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (1)

    Club Clark

    Left on Apr 10, 2014 for a stay in March 2014

    The place was really nice and the staff was very easy to work with. It was a very good vacation and would definitely like to stay there again.

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    $87

    2 BR / 2 BA / Sleeps 4

    7 Reviews

    $87

    Inquire

    Key Lime Pie

    2 BR / 2 BA / Sleeps 4 | Quick view
    “ Very Good ” 7 Reviews

    Details

    Reviews

    (7)

    KEY LIME PIE: One block from the Historic Seaport and close enough to bike to all the sites and attractions of Old Town.Refurbished with updated kitchen cabinets, countertops, and appliances. On the first floor you will find the living room, kitchen, master bedroom and bathroom. On the second floor is the guest …
    • Hot Tub/Jacuzzi
    • A/C or climate control
    • Parking
    • Grill
    • Television
    • Pet friendly
    • Smoking allowed - ask
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (7)

    Cute & Clean

    Left on Nov 06, 2008 for a stay in March 2008

    House is very nice, well kept and supplied, cozy. Good location by Key West Bight waterfront
    Second year we stayed and there were changes in the neighborhhod. Several vacant and unkempt properties, lots of traffic in the alley, several vagrants had to be shooed away from the house. Not returning to this property in 09. A little pricey for the size also.

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    $217

    5 BR / 3 BA / Sleeps 18

    1 / 24

    $217

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    "BAY HARBOR VIEW" - Waterfront Monthly Rental w/ Spectacular Views

    5 BR / 3 BA / Sleeps 18 | Quick view

    Details

    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** a passport tucked away off of mile marker 15. While relaxing in the 20x12 free form lagoon pool, the surrounding scenery makes you feel like you are on your own deserted island. Around the back of the home, the large …
    • Waterfront
    • Internet Access
    • A/C or climate control
    • Patio
    • Fitness Room
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

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    $329

    3 BR / 3 BA / Sleeps 6

    6 Reviews

    $329

    Inquire

    137 Leserra Lane

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

    Details

    Reviews

    (6)

    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 …
    • Ocean or water views
    • Internet Access
    • A/C or climate control
    • Grill
    • Dishwasher
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (6)

    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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    $267

    3 BR / 3 BA / Sleeps 7

    6 Reviews

    $267

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    Your Keys Escape - Luxurious 3bd/3bth Villa

    3 BR / 3 BA / Sleeps 7 | Quick view
    “ Excellent ” 6 Reviews

    Details

    Reviews

    (6)

    Come to the Florida Keys and enjoy living in luxury at 'Blue Heaven'. There are blue skies, crystal clear blue water, calm tropical breezes at 'Blue Heaven' every day. This beautiful new three bedroom, three bath villa has 2,000 square feet on 2 levels with under cover parking. It is located in the new gated community…
    • Waterfront
    • Ocean or water views
    • Hot Tub/Jacuzzi
    • Internet Access
    • Housekeeping Optional
    • Pet friendly
    • Suitable for children
    • Suitable for the elderly - ask

    Details

    Reviews

    (6)

    Great place to spend your vacation

    Left on Sep 29, 2013 for a stay in September 2013

    My husband and I had an amazing time in Marathon with our friends. The home was such a beautiful place and perfectly clean. The beds were so comfortable and the kitchen was well stocked with all the amenities we needed for our stay. The home was equipped with linens, towels, a cooler, and much more! We enjoyed relaxing upstairs in the lounge area with the views of the Gulf during the beautiful…

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    $245

    3 BR / 2 BA / Sleeps 9

    3 Reviews

    $245

    Book

    Tropical House at relaxing paradise !!!

    3 BR / 2 BA / Sleeps 9 | Quick view
    “ Excellent ” 3 Reviews

    Details

    Reviews

    (3)

    Beautiful 2 story 3 bedroom 2 baths home. Located in Key Largo at MM 103 on the bayside and close to John Pennekamp Park, local shopping, fine restaurants, diving, charter fishing or just swimming with the dolphins! This home has an open water view overlooking the beautiful Florida Keys bay, Relax in this tropical …
    • Waterfront
    • Ocean or water views
    • Internet Access
    • Washing Machine
    • Clothes Dryer
    • Pet friendly
    • Suitable for children
    • Suitable for the elderly

    Details

    Reviews

    (3)

    A very clean, cozy and tastefully decorated house with a balcony overlooking a canal

    Left on Feb 05, 2014 for a stay in January 2014

    We stayed at the property for 4 nights. It accommodated us (5 adults and 4 kids) nicely - there were three bedrooms, all rooms being decorated very tastefully. Kind size beds in two bedrooms, a large bunk bed in one bedroom and a sofa in the living room. The kitchen was also nice and there was almost everything we needed. Only one thing - there were not enough cups for all of us so we had to buy …

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    $157

    3 BR / 3 BA / Sleeps 8

    1 / 26

    $157

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    "BEACH CLUB BREEZE" Monthly Rental - Two Story Home w/ Sun Deck & BBQ Grill

    3 BR / 3 BA / Sleeps 8 | Quick view

    Details

    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** This well-manicured, "home away from home" is two stories of wonderful! It has 3 bedrooms, 3 baths and has a colorful, comfortable style. The traditional white picket fence greets you when you arrive. Though, it's only a …
    • Internet Access
    • A/C or climate control
    • Patio
    • Fitness Room
    • Grill
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

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    $615

    5 BR / 6 BA / Sleeps 10

    1 Reviews

    $615

    Book

    OCEAN FRONT VILLA: Great Heron House

    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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    $468

    4 BR / 2 BA / Sleeps 12

    1 Reviews

    $468

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    "SEAPORT SUITE" - Great Party House w/ Hot Tub! 1 Min Walk to Sloppy Joe's

    4 BR / 2 BA / Sleeps 12 | Quick view
    “ Poor ” 1 Reviews

    Details

    Reviews

    (1)

    Seaport Suite is available for daily or weekly vacation rentals and located on the second floor of 219 Simonton in Old Town Key West. The location is as close to perfect as you can get, being one block off Duval Street and within walking distance to every single thing you could possibly want to do. With four bedrooms …
    • Hot Tub/Jacuzzi
    • Internet Access
    • A/C or climate control
    • Balcony or terrace
    • Parking
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (1)

    Seaport Suite not the place to stay

    Left on Dec 02, 2014 for a stay in November 2014

    Rental agents were very helpful can't complain about them or the maintenance staff. The property was not in the best shape. washer dryer didn''t work , had to have it replaced. One bathroom did not drain properly so when showering you could also take a bath. Ants all over the kitchen and bathrooms. Not impressed for the price I paid.

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    $188

    1 BR / 1 BA / Sleeps 4

    23 Reviews

    $188

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    "VERDE SUITE" - Quiet & Affordable 'Old Town' Cottage - Shared Pool

    1 BR / 1 BA / Sleeps 4 | Quick view
    “ Excellent ” 23 Reviews

    Details

    Reviews

    (23)

    The location is ideal in that it is just two blocks from the action of Duval street, yet has the tranquility and peacefulness to nap on the outside deck. This immaculately clean and comfortable air conditioned suite features beautiful vaulted ceilings and pastel colored walls as well as a top of the line flat screen …
    • Shared outdoor pool (unheated)
    • Internet Access
    • A/C or climate control
    • Patio
    • Fitness Room
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (23)

    Verde Suite relaxation

    Left on Jun 25, 2009 for a stay in April 2009

    Glorius week in a great little suite with almost everything you would want. The only thing missing was the availability of authorized parking although there are parking spaces adjacent to the complex that remained vacant the entire week
    Everything else ranks high. Cleanliness, secluded, close to everything in Old Town.

    Would I do it again? In a heartbeat....as a matter of fact I am planning a …

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    $408

    3 BR / 2 BA / Sleeps 10

    13 Reviews

    $408

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    "POOLSIDE PARADISE" Amazing Home 1/2 Block to Duval w/ Pool and Pvt Parking

    3 BR / 2 BA / Sleeps 10 | Quick view
    “ Excellent ” 13 Reviews

    Details

    Reviews

    (13)

    POOLSIDE PARADISE is made up of POOLSIDE RETREAT and POOLSIDE SUITE With 3 bedrooms (K, 2 Q, plus 2 Q sleeper), 2 full baths and 2 full kitchens, this historic home is perfect for up to 10 persons. The front portion features a King bedroom, a Queen bedroom and a Queen sleeper sofa in the living room. The bath with …
    • Internet Access
    • A/C or climate control
    • Deck
    • Fitness Room
    • Grill
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (13)

    Enjoyed our Stay

    Left on Oct 14, 2011 for a stay in September 2011

    The place was perfect for our group. My husband and I traveled with my parents and another couple. It worked out great because the parents stayed with us and our friends had their own little apartment which gave us all our privacy if needed. The location was pretty nice as well. We were one block off Duval. Even though we were down on the end closest to SouthernMost everything was within …

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    $268

    2 BR / 2 BA / Sleeps 6

    1 Reviews

    $268

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    SOUTHERN CROSS @ TROPICAL VILLAGE - Beautifully Updated Home w/ Shared Pool.

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

    Details

    Reviews

    (1)

    Part of TROPICAL VILLAGE Southern Cross: Sitting next to the lily pond with fountain or lounging in the shade of your own Royal Poinciana tree, Southern Cross is the perfect place to relax in paradise. This one and a half story vacation cottage is surrounded by exotic gardens, and situated in the Tropical Village …
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (1)

    Tropical Perfection

    Left on Oct 07, 2014 for a stay in October 2014

    The property was clean, the kitchen was equipped with all the necessities, great private porch and shared pool. Location is great - just a couple blocks from Duval and a 15 minute walk to the Mallory Square. Higgs Beach was a close, great market nearby, and a CVS, you really couldn't have asked for a better location! The trip was epic, relaxing and wild from start to finish. I can't wait to come …

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    $300

    3 BR / 2 BA / Sleeps 8

    1 / 23

    $300

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    Oceanside Key West's Best Luxury Penthouse Condo

    3 BR / 2 BA / Sleeps 8 | Quick view

    Details

    WOW Oceanside Voted #1 Key West's Best Luxury Penthouse Marina/Condo/Pool Direct Oceanfront 1490 Sq Ft Condo, 3 Bedrooms, 2 Baths, (Sleeps 6) Oceanside Marina is one of the newest and one of the most prestigious communities offering breath taking water views and large, open units. The amenities are rounded out …
    • Waterfront
    • Ocean or water views
    • Wireless Internet
    • Housekeeping Optional
    • Washing Machine
    • Pet friendly
    • Suitable for children
    • Suitable for the elderly - elevator access
    • Wheelchair accessible

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    $268

    2 BR / 2 BA / Sleeps 6

    1 / 31

    $268

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    THE COTTAGE @ TROPICAL VILLAGE - Spacious Home w/ Shared Pool. Close To Beach

    2 BR / 2 BA / Sleeps 6 | Quick view

    Details

    Part of TROPICAL VILLAGE Tropical Village Cottage - is a two bedroom, two bath vacation cottage that overlooks a large shared seasonally heated pool, sun-deck and pool-side grilling station. With all the amenities of contemporary living set in island style and decor. Tropical Village Cottage is your ticket to a …
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

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    $118

    2 BR / 1 BA / Sleeps 6

    1 Reviews

    $118

    Inquire

    VO-116

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

    Details

    Reviews

    (1)

    Freshly redecorated canal front home. Living room has a 32' flat screen TV with DVD, two sleeper sofas . Master bedroom has full size bed, mirror closet and a vanity with drawers. Guest bedroom has twin trundel bed with mirror closet and slider doors to patio and canal. Spacious open kitchen area with many …
    • Internet Access
    • Grill
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask

    Details

    Reviews

    (1)

    Nice queit place to stay

    Left on Nov 23, 2013 for a stay in October 2013

    Two bedrooms, living room, full kitchen and bathroom was enough to accommodate five people. Place is quiet, but not very close to public beaches. For the end of October there are many vacant units, so it looks really peaceful. Good resting area on backyard. Internet is not provided, cell phone connection and Internet on phone are poor at house but well enough outside.

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    $110

    2 BR / 2 BA / Sleeps 8

    1 Reviews

    $110

    Book

    Laid Back and Waterfront (Monthly Rental)

    2 BR / 2 BA / Sleeps 8 | Quick view
    “ Excellent ” 1 Reviews

    Details

    Reviews

    (1)

    Minimum rental is 30 days. Our 2/2 modern comfortable house has plenty of dock space (over 100 ft.) and is very close to our community boat ramp. Do you like back-country (shallow water and remote) or deep sea fishing, scuba diving or snorkeling, sailing, nature-watching, canoeing or just relaxing? Then Key …
    • Waterfront
    • Internet Access
    • Housekeeping Optional
    • Washing Machine
    • Clothes Dryer
    • Pet friendly
    • Smoking allowed - ask
    • Suitable for children
    • Suitable for the elderly

    Details

    Reviews

    (1)

    The best time ever in Key Largo....

    Left on Apr 09, 2014 for a stay in March 2014

    I rent a house in Key Largo every year, and this canal side paradise is the best I've ever had. The house is spacious, comfortable and clean. The location is convenient to the places I like to patronize. The huge yard and dock are bright and comfortable, with lots of fish and manatees in the canal. The neighborhood is quiet, especially at night. There is a modern and well equipped kitchen. The …

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    $100

    1 BR / 1 BA / Sleeps 4

    1 / 23

    $100

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    "FRANGIPANI OASIS" Beautifully Decorated Featured Home w/ Pvt Pool

    1 BR / 1 BA / Sleeps 4 | Quick view

    Details

    ***Due to licensing restrictions, this home requires a minimum stay of 28 nights*** This inviting HGTV Featured Home (Bang for Your Buck, 2010) surrounds you with luxury, comfort and history. Originally a Cuban Cigar Maker’s Cottage (circa 1920’s), this vacation home has been updated with no expense spared. …
    • Internet Access
    • A/C or climate control
    • Deck
    • Grill
    • Linens Provided
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

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    $888

    5 BR / 4 BA / Sleeps 12

    1 / 32

    $888

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    "ABBEY ROAD" Great for Big Parties! - 4 Luxury Units - 4 Private Hot Tubs

    5 BR / 4 BA / Sleeps 12 | Quick view

    Details

    Abbey Road - Gated Compound, Sleeps up to 12! Lennon's Lodge (Sleeps 6 with 8 person hot tub), McCartney's Manor (Sleeps 2 with 2 person hot tub), Starr's Suite (Sleeps 2 with 2 person hot tub) and Harrison's Hideaway (Sleeps 2 with 2 person hot tub) and will accommodate up to 12 persons for the ultimate in …
    • Hot Tub/Jacuzzi
    • Internet Access
    • A/C or climate control
    • Balcony or terrace
    • Grill
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    PreviousNext property

    $408

    3 BR / 2 BA / Sleeps 10

    2 Reviews

    $408

    Book

    "TOON HALL @ TROPICAL VILLAGE" - Great For Large Groups. Close to ATL Ocean!

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

    Details

    Reviews

    (2)

    Part of TROPICAL VILLAGE Toon Hall: World-class comfort, lush tropical surroundings and unmatched privacy characterize the former winter home of Pulitzer Prize winning cartoonist, author and artist, Jeff MacNelly. Designed to accommodate a large family or group, this three bedroom home has two full baths plus the …
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

    Details

    Reviews

    (2)

    Best vacation ever!

    Left on Jul 01, 2014 for a stay in June 2014

    We took our family of 6 to Toon Hall and were greeted by 2 Cadillac SUV's at the airport to check us in and take us to our home. Toon Hall was very spacious and comfortable, perfectly situated blocks from the beach and Duvall Street. We were able to chill and grill at home by our pool or walk into town for a night of fun.We also loved the privacy and security the fenced yard offered.

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