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$99

2 BR / 2 BA / Sleeps 8

1 Reviews

$99

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Newly Renovated Executive Bay Townhouse**Discounts Available**

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

Details

Reviews

(1)

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

Details

Reviews

(1)

Great condo, perfect location!

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

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

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$110

2 BR / 1 BA / Sleeps 4

75651 Overseas Hwy Islamorada Fla Keys Oceanfront - Florida Keys vacation rentals
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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$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

Details

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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$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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$270

2 BR / 1 BA / Sleeps 4

Pete's East Cottage: Cypress east cottage steps from Duval - Florida Keys vacation rentals
1 / 13

$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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$113

2 BR / 2 BA / Sleeps 4

South Street Cottage: Bright & sunny in the Casa Marina district - Florida Keys vacation rentals
1 / 11

$113

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South Street Cottage: Bright & sunny in the Casa Marina district

2 BR / 2 BA / Sleeps 4 | Quick view

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30 DAY MINIMUM RENTAL A bright and sunny pool home situated on a quiet street in the Casa Marina district of Key West. Guests can walk to the nearby beaches, artsy White Street, or enjoy the sunny pool and patio space that makes this house the perfect retreat. A large open kitchen, skylights, light tile floors and …
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Patio
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$179

2 BR / 3 BA / Sleeps 4

2 Reviews

$179

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Olivia Cottage: A charming Old Town house near Key West's historic cemetery

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

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Reviews

(2)

30 DAY MINIMUM RENTAL OLIVIA COTTAGE Recently featured in Coastal Living's "Guestbook" column, this charming Old Town house has recently been completely and tastefully renovated by its owners. Located just across the street from Key West's historic city cemetery, truly a tourist attraction in our town, the Oliva …
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Deck
  • Parking
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

Stepping Into a Picture

Left on Jul 21, 2011 for a stay in June 2011

I stayed in Olivia Cottage five weeks and loved every minute. After looking at pictures on the internet, I felt like I was stepping into the pictures. It's exactly as shown. The patio/pool area is just the most relaxing place. Everything I needed was provided and the staff at KW Vacation Rentals were most friendly and helpful. I had one problem with the smoke detectors and it was repaired quickly…

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$320

2 BR / 2 BA / Sleeps 4

36 Reviews

$320

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Catherine House: A charming Old Town Key West cottage

2 BR / 2 BA / Sleeps 4 | Quick view
“ Excellent ” 36 Reviews

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Reviews

(36)

This charming Key West style cottage is just a short walk to a selection of great restaurants, art galleries, and shopping. Catherine House is located only ½ block from the quieter end of Duval Street, and better yet, just three blocks to a beach (Duval & South Streets). The house can comfortably sleep four and …
  • Internet Access
  • A/C or climate control
  • Patio
  • Grill
  • Linens Provided
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(36)

Cozy spot in perfect location

Left on Jun 18, 2009 for a stay in March 2009

Catherine House is truely a shotgun house -- long and narrow -- but has been renovated into a cozy and lovely little two-bedroom. The beds are large and comfy, with two full baths perfect for two couples. The kitchen is basic, but open to the living area and more than sufficient for vacation meals. The pool is more like a tub, but is fine for toddlers and tired parents who want to dip their …

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$270

2 BR / 1 BA / Sleeps 4

1 Reviews

$270

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Pete's West Cottage steps from Duval

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

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Reviews

(1)

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

Details

Reviews

(1)

Nice but could use some sprucing up

Left on Oct 13, 2014 for a stay in October 2014

Nice place. Quiet location. I would have thought someone might clean the pool during our stay since the iguanas in the trees used it for their bathroom quite frequently

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$113

2 BR / 2 BA / Sleeps 6

1 / 17

$113

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Mango Menagerie: A treasury of island colors and Key West charm

2 BR / 2 BA / Sleeps 6 | Quick view

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30 DAY MINIMUM RENTAL Welcome to the Mango Menagerie - a treasury of island colors combined with Key West charm. Located in the heart of Old Town, this home is located just one block from the ever popular Cuban restaurant El Siboney and one block from the local's favorite Flaming Buoy restaurant. The property is …
  • Internet Access
  • A/C or climate control
  • Deck
  • Linens Provided
  • Dishwasher
  • 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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$290

2 BR / 2 BA / Sleeps 5

14 Reviews

$290

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Beach Club #204 - Unique Oceanfront living

2 BR / 2 BA / Sleeps 5 | Quick view
“ Excellent ” 14 Reviews

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Reviews

(14)

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 is one of the most elegant and colorful 2 bedroom units in the Key West Beach Club. It …
  • 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

Details

Reviews

(14)

Great Time

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

I just wish I had the money to buy a condo at The Beach Club. It's the second time I've stayed there and each time was perfect.

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$290

2 BR / 2 BA / Sleeps 6

18 Reviews

$290

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Beach Club #103 - Unique oceanfront living with breathtaking views

2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 18 Reviews

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Reviews

(18)

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 spacious 2 bedroom unit features a large 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

Details

Reviews

(18)

Great Location

Left on Jun 27, 2009 for a stay in April 2009

We are very satisfied with Rent Key West Vacations. The staff was very helpful. We stayed at Key West Beach Club. We were extremely pleased with the Condo we rented, very comfortable, beautiful views of the ocean, it was better than we expected. The kitchen was nicely equipped. We could have used a better vacuum and the washer & dryer combo was very noisy. The pool and grill area were …

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$260

2 BR / 3 BA / Sleeps 4

1 / 28

$260

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"THE FOREVER AFTER HOUSE" KW Golf Club Home on 18th Fairway w/ Pvt Pool, Spa

2 BR / 3 BA / Sleeps 4 | Quick view

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Luxury living on the 18th tee! Arguably the most beautiful home on the Key West golf course, meticulously created by Key West's premier interior designer. The best location to enjoy the peace and quiet with your special friends and family. BBQ on your spacious deck by the private pool. Ready access to the Key West…
  • 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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$320

2 BR / 2 BA / Sleeps 4

30 Reviews

$320

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Havana Lane: A classic conch cottage with rustic charm

2 BR / 2 BA / Sleeps 4 | Quick view
“ Excellent ” 30 Reviews

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Reviews

(30)

Thoughtfully restored, Havana Lane, hearkens back to a time when cigar makers lived in the neighborhood, gathering on porch stoops to pass on the latest news. Near the notorious Key West Cemetery this classic conch cottage, embodies the essence of rustic charm while offering modern amenities and style. Centrally …
  • Internet Access
  • A/C or climate control
  • Deck
  • Grill
  • Linens Provided
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(30)

Gorgeous surroundings, comfortable Key West home

Left on Jun 18, 2009 for a stay in April 2009

As soon as we unlocked the gate to the high wooden fence surrounding 1
Havana Lane, we knew we had picked a gem of a place to stay for Spring Break.
My husband and I came to Key West with our 15 year-old daughter and her
friend. The home was perfect for us four, and we enjoyed being there almost
as much as going out and about the island. We called the yard our "Secret
Garden." It was so lush…

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$143

2 BR / 2 BA / Sleeps 4

1 / 16

$143

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Tropical condo with spectacular ocean view

2 BR / 2 BA / Sleeps 4 | Quick view

Details

14 NIGHT MINIMUM STAY Each unit is fully furnished and has two bedrooms, two bathrooms, dining area, full kitchen, washer/dryer, central heat/airconditioning and a private patio or balcony. This unit has a great corner view of the ocean! The kitchen is equipped with stove, refrigerator, dishwasher, utensils, cookware…
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Fitness Room
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$290

2 BR / 2 BA / Sleeps 6

15 Reviews

$290

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Beach Club #104 - Unique oceanfront living with breathtaking views

2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 15 Reviews

Details

Reviews

(15)

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. The huge oceanfront balcony can be accessed from both the living/dining area and master …
  • 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

Details

Reviews

(15)

Good facility overall, but lots of rules for teeneagers

Left on Apr 16, 2011 for a stay in March 2011

Beach Club #104 is nicely and recently decorated. Everything was in good working order (TVs, washer/dryer, kitchen appliances). The cleaning service could have done a better job. There are a number of loose floor tiles which could be dangerous for older renters. The public areas are well kept, but there are some rather draconian rules -- the owners are not particularly friendly and I have to …

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$209

2 BR / 2 BA / Sleeps 5

11 Reviews

$209

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Best Location, 1/2 Block to Duval, Bimini Suite

2 BR / 2 BA / Sleeps 5 | Quick view
“ Excellent ” 11 Reviews

Details

Reviews

(11)

Located in the heart of Old Town, this split 2 Bedroom plan is just blocks from everything Key West has to offer. The famous Southernmost Point, Hemingway House, Lighthouse, Beaches and more. Just 1/2 block from Duval Street. Completely updated for your comfort and convience with new furnitire, bedding, decor and …
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for the elderly

Details

Reviews

(11)

location! location! location!

Left on Apr 24, 2014 for a stay in April 2014

The location was perfect for going out in Key west! I stayed with 3 other friends and there was plenty of space. The place was clean the bathrooms were nice. The only thing that was a bit of a pain was the parking. its just a driveway you share with the rest of the guests. So one night/ eve I was out and had to go back and move the car so another guest could leave. Aside form that the place was …

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$229

2 BR / 2 BA / Sleeps 8

5 Reviews

$229

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1/2 Block to Duval, World of its own -Nassau Suite

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

Details

Reviews

(5)

The Nassau Suite is one of the largest suites in The Bahama House. Featuring 2 King Bedrooms, 2 Bath and 2 Day-rooms with Futons. Quietly Tucked away in a world of it's own, yet literally only steps away from all that Key West has to offer. Whether your looking for a place to meditate or find an endless party, The …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for the elderly - ask

Details

Reviews

(5)

Wish I had found this place 15 years ago.

Left on Jan 06, 2014 for a stay in December 2013

Stayed in the Nassau the week of Christmas thru New Years. Came down with two other couples. The pictures do not do this place justice. Plenty of room for all. Having two bathrooms was also a plus. Very close to Duval street, and anywhere you really would want to go is in walking distance, minus the beach, but is a short/cheap taxi ride away. Our unit had 90% new furniture, and matresses. …

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$171

2 BR / 0 BA / Sleeps 6

1 / 21

$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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$270

2 BR / 1 BA / Sleeps 4

43 Reviews

$270

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Key Lime Calypso: A cottage in the heart of Bahama Village

2 BR / 1 BA / Sleeps 4 | Quick view
“ Very Good ” 43 Reviews

Details

Reviews

(43)

The best of Key West, in the middle of Historic Old Town and a half block from Duval Street and the gates to Bahama Village, a perfect location for visitors to our Island. Guests can stroll to Mallory Square, Fort Zachary Beach or the sunset piers which are all within easy walking distance of this two bedroom cottage…
  • Internet Access
  • A/C or climate control
  • Deck
  • Parking
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(43)

Lovely cottage and great location

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

The cottage was a great "get away from it", but yet was right in the heart of the main area Key West, just off Duval St. As the property was centrally located along Duval St, it was also quiet and peaceful. The private pool was great to have and the garden had a lovely sunny aspect, but there was enough shade to get out of the sun if you wanted too. The pool was welcome as the main beaches on the…

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$290

2 BR / 2 BA / Sleeps 6

15 Reviews

$290

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Beach Club #201 - Unique Oceanfront living

2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 15 Reviews

Details

Reviews

(15)

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 2 bedroom, 2 bath unit features a huge oceanfront balcony accessed from both the living/…
  • 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

Details

Reviews

(15)

Key West Wedding Vacation

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

We loved staying at the condo.. It fit 5 of us very comfortably. We were down for a wedding. The view was great, the securty made me feel safe. We used the pool almost daily and actually had a couple of friends over for a cookout by the pool. I would stay with Rent Key West Vacations again and would recommend it to a friend.

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$149

2 BR / 2 BA / Sleeps 4

1 / 1

$149

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Moon Bay Condo A-206

2 BR / 2 BA / Sleeps 4 | Quick view

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A beautifully decorated condo located at mm 104. This unit has 2 bedrooms and 1.5 baths and its own deeded boat slip. This condo in conveniently located close to the main land. This is a perfect condo for fishermen, divers, or just a Key's getaway. Amenities include heated pool, jacuzzi, tennis courts, sauna, and game…
  • Shared outdoor pool (unheated)
  • Sauna
  • Internet Access
  • A/C or climate control
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$270

2 BR / 2 BA / Sleeps 6

21 Reviews

$270

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Vista Fresco : Oceanside condominiums with resort-style amenities

2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 21 Reviews

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Reviews

(21)

Enjoy the resort-style amenities of 1800 Atlantic Condominiums while relaxing in a residential setting amongst neighbors. 1800 Atlantic sits on 400 feet of oceanfront property. An expansive pool and spa sits oceanside surrounded by a lushly landscaped garden of native Key West plants and trees. Plan a picnic or …
  • 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

Details

Reviews

(21)

The appart was fantastic but it was impossible to use the pool.

Left on Aug 12, 2009 for a stay in July 2009

If there wasn't any pool at this condo, we'd never rent it. Unfortunatly, the pool
was broken and it was impossible to use it. We arrived on thurdays and friday,
the pool was broke. We ask to know when it would be repare, they told us it
would be the next monday but when we left on thursday night, the pool was
still broke... This point realy desapoint us.

For the condo, everything was …

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$77

2 BR / 2 BA / Sleeps 4

1 / 21

$77

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Executive Bay Club A-1

2 BR / 2 BA / Sleeps 4 | Quick view

Details

N/A
  • Shared outdoor pool (unheated)
  • A/C or climate control
  • Dishwasher
  • Microwave
  • Toaster
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$258

2 BR / 3 BA / Sleeps 6

3 Reviews

$258

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Islamorada Luxury Waterfront Condo with Boat Slip

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

Details

Reviews

(3)

Escape to Islamorada in the Florida Keys and enjoy the breathtaking gulf and ocean views from your top floor balcony in this decorator furnished, two bedroom luxurious condo. This unit located in the complex of Bay Harbour offers a private 50' boat slip, heated swimming pool, hot tub, club house, fitness center, …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Suitable for children
  • Suitable for the elderly - elevator access
  • Wheelchair accessible

Details

Reviews

(3)

Wonderful stay at Bay Harbour

Left on Jan 24, 2014 for a stay in January 2014

This condo exceeded our expectations. It was truly a home away from home. It has all the amenities you will need to have a great vacation. The kitchen is fully furnished, the condo is spacious, and the little extras like bikes, tennis rackets, and baseball gloves are an added bonus.

Our family was happy to see a manatee and calf in the water right outside the condo!

Pool was very …

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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

Details

Reviews

(2)

This 2Bed/2Bath stilt home is located at mile marker 89 at the very end of Indian Waterways subdivision. Located on a canal with approximately 30' of dockage, you'll have almost immediate access to the Florida Bay and just a 7 minute boat ride to Tavernier Creek, which takes right over to the Atlantic Ocean. The yard …
  • 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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$190

2 BR / 3 BA / Sleeps 4

1 Reviews

$190

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Futura Townhome 731

2 BR / 3 BA / Sleeps 4 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

Enjoy the spectacular view of the Florida Bay from this beautiful townhome. There are tons of things to keep you and your family busy without having to leave the Futura Condo complex. There are tennis courts and a swimming pool located on the property. Make your self at home in our home away from home. Boat dockage …
  • Waterfront
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • A/C or climate control
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Most awesome vacation in Islamorda Florida!!

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

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

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$214

2 BR / 3 BA / Sleeps 6

1 / 24

$214

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LUXURY KEYS HOME IN PARADISE-106 ANGLERS REEF

2 BR / 3 BA / Sleeps 6 | Quick view

Details

This beautiful villa has all new furnishings and is located in the exclusive oceanfront gated community of Angler's Reef in Islamorada at Mile Marker 84. Angler's reef is a luxury retreat resort framed by mangroves and the clear waters of the Atlantic ocean with 52 colonial detached villas set along quaint streets …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Suitable for children
  • Suitable for the elderly

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$83

2 BR / 0 BA / Sleeps 4

1 / 19

$83

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135 Gulfview Dr

2 BR / Sleeps 4 | Quick view

Details

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

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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

Details

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

Details

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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$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

Details

Reviews

(2)

Great house in Lower Matecumbe (south side of Islamorada) at the 75 mile marker on the bayside. This house has fabulous sunset views in a nice quiet part of town. There is a small beach area in the back with palm trees giving you a little more privacy. A screened in porch with tables and chairs makes for a great …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Television
  • Pet friendly
  • 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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$171

2 BR / 2 BA / Sleeps 4

1 / 11

$171

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VO-198

2 BR / 2 BA / Sleeps 4 | Quick view

Details

Wrap around open water view with a huge 61' concrete dock/seawall, complete with cleats, padded aluminum dock posts,mooring whip holders,and hose. Covered deck with lounge furniture to dine out or enjoy an evening drink. Or eat inside on upscale dining set and still enjoy the million dollar ocean view. Kitchen is…
  • Internet Access
  • Grill
  • Satellite or cable TV
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$107

2 BR / 0 BA / Sleeps 4

1 / 20

$107

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114 Plantation Ave

2 BR / Sleeps 4 | Quick view

Details

This charming 2 bedroom, 2 bathroom home is located at the 90 mile marker. This home is centrally located to shopping, restaurants, and grocery store.
  • 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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$250

2 BR / 3 BA / Sleeps 6

1 / 7

$250

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Angler's Reef Coastal Conch Style Vacation Home

2 BR / 3 BA / Sleeps 6 | Quick view

Details

This Coastal Conch Style Cottage has been recently updated to accommodate vacation renters and their families. The cottage has all new furnishings and accessories that offers a "home away from home" feel. The Coastal style conch cottage is located in the gated community, ocean front resort development of Angler's Reef…
  • Suitable for children
  • Suitable for the elderly

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$100

2 BR / 2 BA / Sleeps 6

2 Reviews

$100

Inquire

Summer Sea #418 - 28 Night Minimum

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

Details

Reviews

(2)

This 2 bedroom, 2 bathroom condo located directly on the Florida Bay is the perfect sunny getaway! Situation with perfect views of the community pool, community marina, and open bay, you'll enjoy coffee in the morning while watching the boaters head out for their perfect catch and enjoy a sunset cocktail in the …
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • A/C or climate control
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

Heaven in Islamorada, Florida

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

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

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$117

2 BR / 2 BA / Sleeps 4

2 Reviews

$117

Inquire

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

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

Details

Reviews

(2)

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

Details

Reviews

(2)

Relaxing

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

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

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$230

2 BR / 2 BA / Sleeps 5

2 Reviews

$230

Inquire

Royal Palm

2 BR / 2 BA / Sleeps 5 | Quick view
“ Very Good ” 2 Reviews

Details

Reviews

(2)

There's no better way to experience "Island Time"-that slow shifting of hours that makes Key West such an ideal vacation spot-than staying at Royal Palm. Located in the prestigious Foundry building within the exclusive Truman Annex gated community, this two-bedroom, three-story brick townhouse offers privacy and …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Central heating
  • Suitable for the elderly - ask

Details

Reviews

(2)

Really Great Experience

Left on Mar 15, 2013 for a stay in February 2013

Had a great time. Historic Hideaways was very helpful. Our place was central to everything, very clean. Perfect for our needs.

Thank you.

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$400

2 BR / 2 BA / Sleeps 4

10 Reviews

$400

Inquire

Casa Camilla

2 BR / 2 BA / Sleeps 4 | Quick view
“ Excellent ” 10 Reviews

Details

Reviews

(10)

You'll know you've found island heaven--the term heaven meaning transcendence or going beyond the ordinary--when you enter Casa Camilla. This two-bedroom, two-bathroom home located in the lovely Meadows neighborhood of Old Key West is extraordinary inside and out. The outside rear half of the property is beautifully …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for the elderly - ask

Details

Reviews

(10)

absolutely gorgeous!

Left on Dec 07, 2011 for a stay in November 2011

The house is absolutely beautiful and in a great location; easy to get to Duval street. Very quiet neighborhood. The house had everything except internet access and a heated pool/jacuzzi.

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$213

2 BR / 2 BA / Sleeps 6

1 Reviews

$213

Inquire

VO-093

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

Details

Reviews

(1)

180 degree wrap around porch with patio furniture. 42' seawall with dock posts, cleats, fish cleaning table, swim ladder and outdoor shower. Panoramic view from front room with three sets of glass sliders. TV, DVD player, queen sleeper sofa. Kitchen island, side by side refrigerator with water dispenser. Master …
  • Internet Access
  • Grill
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(1)

Fabulous ocean views

Left on Mar 07, 2013 for a stay in February 2013

We absolutely loved every minute of our stay in Venture Out#93. The house was very clean and decorated in a wonderful tropical décor. We didn't want for anything...if anything, it was better than thought it would be. Being right on the water was spectacular, especially in the morning with the sunrise. We did not want to leave. Hard to complain about anything, but we were wondering where the …

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$147

2 BR / 2 BA / Sleeps 5

7 Reviews

$147

Inquire

Ocean Pointe 5202

2 BR / 2 BA / Sleeps 5 | Quick view
“ Excellent ” 7 Reviews

Details

Reviews

(7)

Enjoy your vacation in this recently remodeled 2 bedroom 2 bath Condo. Just off the living room and master bedroom, you can sit on your balcony that looks over the crystal clear waters of the Atlantic and the marina. There are lots of things to do in the complex from swimming in the pool, relaxing in the jacuzzi, …
  • Waterfront
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • A/C or climate control
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(7)

Comfortable apartement - Key Largo, Tavernier

Left on Jan 24, 2012 for a stay in December 2011

Very cosy place, Everything was there - condiments, kitchen paper, sponge for the dishes, towels, torches, books, games, etc. etc. Great view from the balcony. Good position within the Ocean Pointe suites, close to everywhere.

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$100

2 BR / 2 BA / Sleeps 6

2 Reviews

$100

Inquire

60 Waterways Dr - 28 Night Minimum

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

Details

Reviews

(2)

Q: What's better than vacationing in the Florida Keys? A: Vacationing in a charmingly cute canal-front home in the Florida Keys! And this home takes the cake for cute! Located at mile marker 101 on the bay-side in Key Largo, this home is equipped to make your month (or longer!) in the Keys one to remember. Home …
  • Waterfront
  • Internet Access
  • A/C or climate control
  • Porch
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(2)

Bonita y confortable

Left on Jan 18, 2014 for a stay in December 2013

Una casa muy cómoda y espaciosa, con vistas preciosas y en un barrio muy agradable. Tiene todas las comodidades. Dispone de dos canoas y muelle propio. En el canal hay manatíes; los niños han jugado mucho con ellos. Si se viene de vacaciones a Key Largo se necesita un coche de alquiler.

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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

Details

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

PreviousNext property

$195

2 BR / 2 BA / Sleeps 6

1 / 31

$195

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Direct and easy gulf access!

2 BR / 2 BA / Sleeps 6 | Quick view

Details

Beautiful two bedroom, two bath home in Marathon has a fantastic Gulf view and quick, easy access to open water! Very spacious, concrete dock, sundeck on top of home makes for spectacular sunrise and sunset scenes. Master bedroom has king bed with sitting area and full bath. Second bedroom has a queen size bed. …
  • Ocean or water views
  • Internet Access
  • A/C or climate control
  • Patio
  • Fitness Room
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$215

2 BR / 1 BA / Sleeps 6

1 / 6

$215

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The Banyan Resort at Key West

2 BR / 1 BA / Sleeps 6 | Quick view

Details

Experience a world full of lush and fragrant gardens on a Caribbean Estate tucked away in the heart of Old Town, Key West. Stay in a 2 bedroom unit in a restored historic wrecker's home and wander through the extensive gardens as time transcends you to an era long ago. You can relax and indulge yourself at this …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Outdoor Dining Area
  • A/C or climate control
  • Central heating
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - ask

PreviousNext property

$171

2 BR / 2 BA / Sleeps 6

1 / 11

$171

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VO-194

2 BR / 2 BA / Sleeps 6 | Quick view

Details

Just three lots in from the open water!! Newly renovated and sophisticatedly decorated vacation home has an ocean view from 35’ concrete seawall. Dock has posts and cleats for mooring your boat also lounge furniture and mosaic picnic table for relaxing and dining al fresco. Living room with canal view has flat …
  • Internet Access
  • Satellite or cable TV
  • Ceiling Fans
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$199

2 BR / 1 BA / Sleeps 6

15 Reviews

$199

Book

Center of It All - Paradise Island Suite

2 BR / 1 BA / Sleeps 6 | Quick view
“ Excellent ” 15 Reviews

Details

Reviews

(15)

Relax of the Island Style front porch and enjoy Key West at it's finest. Centrally located, less than a block from Duval - this Completely updated 2 Bedroom, 1 Bath will simply amaze you! High Ceilings, tall windows, full kitchen with separate dining room and plenty of space to make your Key West vacation memorable…
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for children - ask
  • Suitable for the elderly

Details

Reviews

(15)

Great Locaction!!

Left on Nov 08, 2013 for a stay in October 2013

Great location! loved the apartment, will definitely rent there rent it again. If I had to complain about 1 thing, the beds where awful!!!
But I was told there changing all the furniture so the place is perfect! loved it!

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$400

2 BR / 2 BA / Sleeps 4

2 Reviews

$400

Inquire

Quilted Giraffe

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

Details

Reviews

(2)

This home has a unique pricing structure. While it can rent for less than 30 days, the owner prefers Monthly rentals. Because of this, this home offers substantial (25% off) Monthly Rental discounts. Your space. Your vacation lifestyle. The Quilted Giraffe provides both. This two-bedroom, two full bath home welcomes …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for the elderly - ask

Details

Reviews

(2)

Relaxing respite

Left on Mar 05, 2010 for a stay in February 2010

The heated pool and lush backyard foliage were the draw to this well appointed home. Parking was a nightmare, the neighbor to the right facing the house was most unpleasant. A parking spot in the front yard would be recommended. The location was excellent for walking anywhere. The service was good once we met Bill. Prior to him, Corey and Libby both seemed disorganized and inattentive to our …

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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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$255

2 BR / 2 BA / Sleeps 5

10 Reviews

$255

Inquire

Havana Hideaway

2 BR / 2 BA / Sleeps 5 | Quick view
“ Excellent ” 10 Reviews

Details

Reviews

(10)

Call it casual luxury. Call it tropical chic. This two bedroom/two full bath Harbour Place condominium is a part of Key West's prestigious Truman Annex community. From the luxurious pool area below, you can enjoy breathtaking views just steps from the Gulf of Mexico. Watch passing tall ships, cruise ships, pleasure …
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Suitable for the elderly - ask

Details

Reviews

(10)

Week in Paradise

Left on Jan 16, 2013 for a stay in December 2012

This was one of the greatest stays that we have had. Condo was within walking distance to everything block to most. Very nice place to stay. Easy check in and check out process. This place has a great view from pool. We were here in December with about 80 degree temps each day so we shut down the air and had the doors open most of the time the only draw back to this is the chickens will wake…

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