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$308

3 BR / 4 BA / Sleeps 8

La Dolce Vita - Luxury Monthly Rental Private heated pool - Key West vacation rentals
1 / 21

$308

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La Dolce Vita - Luxury Monthly Rental Private heated pool

Key West house
3 BR / 4 BA / Sleeps 8 | Quick view

Details

***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Located in one of Key West's best neighborhoods just a short walk from Higgs and Smathers beaches, La Dolce Vita offers uncommon space and the finest of appointments throughout. Upon entering the gated property complete with…
  • 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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$198

2 BR / 2 BA / Sleeps 6

SAINT LUCIA SUITE #201 - 2/2 Condo w/ Pool & Hot Tub - Near Smathers Beach - Key West vacation rentals
1 / 22

$198

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SAINT LUCIA SUITE #201 - 2/2 Condo w/ Pool & Hot Tub - Near Smathers Beach

Key West condo
2 BR / 2 BA / Sleeps 6 | Quick view

Details

Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$180

2 BR / 3 BA / Sleeps 6

13 Reviews

$180

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Coral Suite

Key West condo
2 BR / 3 BA / Sleeps 6 | Quick view
“ Very Good ” 13 Reviews

Details

Reviews

(13)

CORAL SUITE: 2 bedroom 3 bath townhome for 6 people, and your pet! Both bedrooms (ensuite) are on the 2nd floor of this stilt home. Master bedroom has a private balcony. Guest bedroom is roomy and private. The Murphy bed in the living room is sturdy and comfortable.Kitchen is equipped with all of the essentials. …
  • Shared outdoor pool (unheated)
  • A/C or climate control
  • Balcony or terrace
  • Parking
  • Television
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(13)

nice

Left on Jul 13, 2012 for a stay in June 2012

Enjoyed the community, and condo. It was nice, and relaxing - just what we needed for our vacation. Its located on stock island, so we drove to do a lot. Especially downtown key west. we ordered pizza one night, and didn't have an exact address to give them (it wasn't listed in the paper work, and I couldnt find it on the.Internet making it a hassle to order in) luckily, the pizza place was nice …

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$778

4 BR / 5 BA / Sleeps 12

1 / 30

$778

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"HAVANA OASIS" Luxury 2-Home, Group Rental w/ 2 Pvt Pools. Sleeps 12!

Key West house
4 BR / 5 BA / Sleeps 12 | Quick view

Details

Island Oasis The beaches of the Atlantic Ocean are less than a 7 minute blocks away. This ultra luxurious 2 bedroom, 2-1/2 bath, 2 story house has been totally redecorated by one of Key West’s most talented designers, Michael Pelkey. Sitting in a row of 6 townhomes built by Key West's premier builder, Island …
  • 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

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$198

2 BR / 2 BA / Sleeps 6

1 Reviews

$198

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VIRGIN GORDA SUITE #310 - 2/2 Condo w/ Pool & Hot Tub - Near Smathers Beach

Key West condo
2 BR / 2 BA / Sleeps 6 | Quick view
“ Average ” 1 Reviews

Details

Reviews

(1)

Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped …
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Fitness Room
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Top notch customer service

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

When we arrived they did not have our reservation in their system eve though I had prepaid. I booked through a third party. I showed them my receipts and they put us in a room before they had verified that I hadn't been dooped by a scam artist.

Room was hard to find, office closed at 5pm, room was quite old but bathrooms and kitchen were clean, rug was new but installed too loosely in the …

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$138

4294967295 BR / 1 BA / Sleeps 4

1 / 26

$138

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"PELICAN SUITE @ THE SANCTUARY" Old Town Suite - Hot Tub & BBQ Grill

Key West cottage
1 BA / Sleeps 4 | Quick view

Details

Part of Southernmost Suites The Pelican Suite is located in The Southernmost Suites on historic Simonton Street. Tucked back within the garden the Spoonbill Suite offers a serene escape from the hustle and bustle. The Pelican Suite has 2 Queen Beds and a kitchenette for you to enjoy meals in before you hit the …
  • Patio
  • Grill
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$93

1 BR / 1 BA / Sleeps 4

1 / 14

$93

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"BOARDWALK LOFT" - Monthly Rental - Newly Renovated Condo w/ Shared Pool.

Key West condo
1 BR / 1 BA / Sleeps 4 | Quick view

Details

***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Beautiful Getaway Spot w/ Pool! Boardwalk Loft is the perfect getaway spot for families, or for individuals that just need some peace and quiet. The interior exudes elegance from top to bottom. You will fall in love with …
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Deck
  • Grill
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$465

3 BR / 2 BA / Sleeps 8

78 Reviews

$465

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Bahama Dreaming

Key West house
3 BR / 2 BA / Sleeps 8 | Quick view
“ Excellent ” 78 Reviews

Details

Reviews

(78)

BAHAMA DREAMING: 3-bedroom Conch cottage with outdoor dining and private pool, fenced and landscaped, off-street parking, 1/2 block from Duval Street. Downstairs has 2 bedrooms (queen and 2 twins), living room with sleeper sofa and full bathroom, kitchen and covered back porch. A couple steps down to the 12'x18' …
  • Internet Access
  • 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

(78)

cozy, clean home

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

Decent, small home with all of the necessary amenities and
close to town. We have rented many places in and around
Florida. This was a smaller home. The front bedroom faced the
road and was quite bright and loud early in the morning.

There was a lot of construction noise around, so, we
had to turn up our music when in the pool. The pool was
beautiful but there were no pool toys. They …

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$198

2 BR / 2 BA / Sleeps 6

1 / 36

$198

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CATALINA SUITE #311 - 2/2 Condo w/ Pool & Hot Tub - Near Smathers Beach

Key West condo
2 BR / 2 BA / Sleeps 6 | Quick view

Details

Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$160

1 BR / 1 BA / Sleeps 4

27 Reviews

$160

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Paradise Place

Key West condo
1 BR / 1 BA / Sleeps 4 | Quick view
“ Very Good ” 27 Reviews

Details

Reviews

(27)

PARADISE PLACE: Ground level 1-bedroom 1-bath condo in the Palm Gardens community just 6 blocks from Duval Street.Completely renovated, this lovely property offers hardwood floors and cabinets, granite kitchen countertop and beautifully tiled bath.Queen size sleeper sofa in living room and 50" HDTV. Kitchen is …
  • Hot Tub/Jacuzzi
  • A/C or climate control
  • Television
  • DVD Player
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(27)

Noisy

Left on Mar 10, 2010 for a stay in March 2010

The rental company 'At Home in Key West' is good as far as property management companies go. The service was good. I have rented many properties in different locations over the years, and they match up with them.

The house/condo on the other hand was a different story. The property was ok, but it had small TV’s mounted close to the ceiling which weren’t great and a live cockroach in the …

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$198

2 BR / 2 BA / Sleeps 6

1 / 23

$198

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HISPANIOLA SUITE #101- 2/2 Condo w/ Pool & Hot Tub - 1 Mile To Smathers Beach

Key West condo
2 BR / 2 BA / Sleeps 6 | Quick view

Details

Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped…
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$198

2 BR / 2 BA / Sleeps 6

1 / 27

$198

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SAINT THOMAS SUITE #302 - 2/2 Condo w/ Pool & Hot Tub - Near Smathers Beach

Key West condo
2 BR / 2 BA / Sleeps 6 | Quick view

Details

Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$183

3 BR / 3 BA / Sleeps 10

1 / 24

$183

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"CAYO HUESO HIDEAWAY' - Luxury Monthly Rental - Pvt Pool & Pvt Hot Tub

Key West house
3 BR / 3 BA / Sleeps 10 | Quick view

Details

***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Cayo Hueso: As you approach the front door to 1120 Curry Lane the transformation starts to happen. The small lush tropical lane, the two wonderfully inviting porches... your journey to the tropics and relaxation has begun! …
  • 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

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$198

2 BR / 2 BA / Sleeps 6

1 / 24

$198

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SAINT CROIX SUITE #212 - 2/2 Condo w/ Pool & Hot Tub - Near Smathers Beach

Key West condo
2 BR / 2 BA / Sleeps 6 | Quick view

Details

Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$198

2 BR / 2 BA / Sleeps 6

1 / 22

$198

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GRAND BAHAMA SUITE #106 - 2/2 Condo w/ Pool & Hot Tub - Near Smathers Beach

Key West condo
2 BR / 2 BA / Sleeps 6 | Quick view

Details

Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$198

2 BR / 2 BA / Sleeps 6

1 / 24

$198

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COZUMEL SUITE #112 - 2/2 Condo w/ Pool & Hot Tub - Near Smathers Beach

Key West condo
2 BR / 2 BA / Sleeps 6 | Quick view

Details

Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$258

2 BR / 1 BA / Sleeps 6

35 Reviews

$258

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"LEEWARD ISLE" - Private Hot Tub - Private Parking - 1/2 Block To Duval St.

Key West house
2 BR / 1 BA / Sleeps 6 | Quick view
“ Excellent ” 35 Reviews

Details

Reviews

(35)

One half of the group unit Tradewinds Opposite Windward Isle , the Leeward Isle sits at 529 Olivia Street, right in the center of Old Town Key West, just 1/2 block from Duval Street. This superb example of shotgun style architecture is complimented with original Dade County pine floors and walls, which were …
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Deck
  • Fitness Room
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(35)

A Great Week At Key West

Left on Jun 24, 2009 for a stay in July 2008

We thoroughly enjoyed staying at the Leeward Isle residence. The room was very convenient to everything we wanted to do. Even though it was in the heat of summer, the rooms stayed very cool and the amenities were great!! We will stay again when we plan our next trip to Key West. Highly recommend this property for a family rental.

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$198

2 BR / 2 BA / Sleeps 6

1 / 22

$198

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DOMINICAN SUITE #110 - 2/2 Condo w/ Pool & Hot Tub - Near Smathers Beach

Key West condo
2 BR / 2 BA / Sleeps 6 | Quick view

Details

Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$83

1 BR / 2 BA / Sleeps 4

6 Reviews

$83

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"PARADISE SUITE" Monthly Villa In Gated Complex w/ Pool. Steps to Duval St

Key West house
1 BR / 2 BA / Sleeps 4 | Quick view
“ Excellent ” 6 Reviews

Details

Reviews

(6)

***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Nestled in extensive tropical and flowering gardens, complete with aviaries with singing cockatiels lays the Paradise Suite. Paradise Suite (renovated for January 2013) is a bi-level suite with one bedroom upstairs. The …
  • 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

(6)

Great time in Keys at Esperanza

Left on Jan 28, 2011 for a stay in October 2009

Very Nice! Great location for Fantasy Fest and the Parrothead music week that follows. Separate upstairs bedroom and a couch downstairs with its own bathroom was great for a short term friend to stay. Very private with the courtyard and gate. We really liked it...

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$340

2 BR / 3 BA / Sleeps 6

51 Reviews

$340

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Tropical Dreaming

Key West house
2 BR / 3 BA / Sleeps 6 | Quick view
“ Excellent ” 51 Reviews

Details

Reviews

(51)

TROPICAL DREAMING: This tropical 2-bedroom home with classic art features, hardwood floors, tall ceilings, new appliances, new furnishings and a true Key West feel. One block from Duval Street , it is close to restaurants, shops, galleries and clubs. The Atlantic Ocean is only 4 blocks away. The living room has …
  • Internet Access
  • 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

(51)

Nice home for relaxing

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

This home was as nice as the pictures. The pool was great. The home was close enough to all the action but quite at night.

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$248

1 BR / 1 BA / Sleeps 2

1 / 20

$248

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"BANANA SPLIT"

Key West condo
1 BR / 1 BA / Sleeps 2 | Quick view

Details

Part of Banana's Foster Guest House This one bedroom apartment is on the 2nd floor of this historic property and accessed through the shared gated courtyard, right beside the shared off street parking on Simonton. Once through the gates, walk around the shared plunge pool and BBQ grill, going upstairs to the large …
  • 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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$208

4294967295 BR / 1 BA / Sleeps 2

15 Reviews

$208

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"McCARTNEY'S MANOR" Luxury Cottage - Private Hot Tub - 1/2 Block To Duval St!

Key West cottage
1 BA / Sleeps 2 | Quick view
“ Excellent ” 15 Reviews

Details

Reviews

(15)

Part of 4 exclusive units at Abbey Road, The state-of-the-art kitchen includes granite counter tops, a Jenn-Air 2 burner cook top, dishwasher, under counter refrigerator, microwave and soft mood lighting under and above the cabinets. There is also an ice-maker on site for fresh ice to prepare your tropical drinks in …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Deck
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(15)

Best vacation inside us ever!

Left on Sep 06, 2010 for a stay in July 2010

Came down to Key West with my fiancée and wow we were surprised our room the mcarthy manor was wonderful ! The decorated immaculately! Everything was too of the line including the appliances. Never had a problem finding parking for our car. When I come back I won't stay anywhere else! Neither should you! The privacy and beauty of these rooms cant be top anywhere else on the island. And the pool …

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$183

3 BR / 3 BA / Sleeps 6

1 Reviews

$183

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

Key West house
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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$188

4294967295 BR / 1 BA / Sleeps 2

1 Reviews

$188

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"ROYAL PALM" Bahama Village Cottage - Pvt Hot Tub - Perfect for Couples

Key West cottage
1 BA / Sleeps 2 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

Part of Southern Palms ROYAL PALM (formerly Little Palm) - What an idyllic setting! Picture the most perfect romantic getaway cottage with all the must have's for a great Key West vacation - in a setting that nature provided in the late 1800's - the hardwood canopy is stunning! The Tommy Bahama furniture is set off…
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

The Perfect Key West hideaway

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

This was our second extended stay in this unit and we absolutely love it! You can't beat the location or the privacy of the unit. It's a perfect unit for two! There's a few little things that could be updated in the unit, but overall its a great value for the money!!

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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

Key West house
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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$198

2 BR / 2 BA / Sleeps 6

1 / 22

$198

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TORTUGA SUITE #301 - 2/2 Condo w/ Pool & Hot Tub - Near Smathers Beach

Key West condo
2 BR / 2 BA / Sleeps 6 | Quick view

Details

Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$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

Key West cottage
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

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$1,028

5 BR / 6 BA / Sleeps 14

1 / 42

$1,028

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"BANANA'S FOSTER" 5 / 5.5 Guest House 1 Block to Duval St! Pvt Pool & Parking

Key West house
5 BR / 6 BA / Sleeps 14 | Quick view

Details

When rented as a group, Banana’s Foster includes- Sweet Caroline - Banana Split - Key Lime Cottage Creme Brûlée All together this grouping has 5 separate bedrooms, each with it’s own bathroom and a ½ bath downstairs, 2 full kitchens, a BBQ grill and shared courtyard with a plunge pool. The historic…
  • 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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$368

2 BR / 3 BA / Sleeps 6

1 / 25

$368

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"SWEET CAROLINE"

Key West condo
2 BR / 3 BA / Sleeps 6 | Quick view

Details

Part of Banana's Foster Guest House This spacious 2 bedroom apartment takes up the first floor of this historic home. From the off street parking and shared courtyard entrance off Simonton opening into the kitchen to the private front entrance with sweeping front porch over Caroline Street- this rental has a lot to…
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Patio
  • Parking
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$1,448

11 BR / 9 BA / Sleeps 32

1 / 32

$1,448

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TROPICAL VILLAGE 6 Homes w/ Pvt Pool & BBQ Grill. Great For Large Parties!

Key West house
11 BR / 9 BA / Sleeps 32 | Quick view

Details

Tropical Village is comprised of 6 separate vacation rentals properties that can also be rented separately. COTTAGE @ TROPICAL VILLAGE POOLSIDE @ TROPICAL VILLAGE SOUTHERN CROSS @ TROPICAL VILLAGE TOON HALL @ TROPICAL VILLAGE RETREAT @ TROPICAL VILLAGE HIDEAWAY @ TROPICAL VILLAGE Located at 706 and…
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$208

4294967295 BR / 1 BA / Sleeps 2

19 Reviews

$208

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"HARRISONS HIDEAWAY" Luxury Cottage - Private Hot Tub - Half Block To Duval

Key West cottage
1 BA / Sleeps 2 | Quick view
“ Excellent ” 19 Reviews

Details

Reviews

(19)

Part of 4 exclusive units at Abbey Road, renovated January, 2010, this free standing historic cottage at 918-920 Center Street, features a king pillow-top bed, 2 lushly padded swivel chairs and a full kitchen which includes a full stove, refrigerator with ice-maker, microwave, dishwasher and soft mood lighting under …
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Deck
  • Fitness Room
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(19)

Relaxation

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

Enjoyed a very relaxing stay in Key West. With access to the pools, hot tub and restaurants, much to chose from.

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$198

2 BR / 2 BA / Sleeps 6

1 / 27

$198

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JAMAICA SUITE #102 - 2/2 Condo w/ Pool & Hot Tub - 1 Mile To Smathers Beach

Key West condo
2 BR / 2 BA / Sleeps 6 | Quick view

Details

Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$198

2 BR / 2 BA / Sleeps 6

1 / 24

$198

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PUERTO RICO SUITE #103 - 2/2 Condo w/ Pool & Hot Tub - Near Smathers Beach

Key West condo
2 BR / 2 BA / Sleeps 6 | Quick view

Details

Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped…
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$198

2 BR / 2 BA / Sleeps 6

1 / 28

$198

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GREAT EXUMA SUITE #406 - 2/2 Condo w/ Pool & Hot Tub - Near Smathers Beach

Key West condo
2 BR / 2 BA / Sleeps 6 | Quick view

Details

Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$418

3 BR / 3 BA / Sleeps 8

8 Reviews

$418

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"CASA MARGARITA" Amazing Location w/ Pvt Pool & Huge Deck. Pvt Parking

Key West house
3 BR / 3 BA / Sleeps 8 | Quick view
“ Excellent ” 8 Reviews

Details

Reviews

(8)

Casa Margarita is located on the 300 block Margaret Street in one of Old Town Key West’s most desirable locations. This 3 bedroom/3 bathroom home features a large backyard with lush tropical landscaping placed for an ultimate privacy that is rarely seen in Old Town. The heated pool is flanked by a large covered …
  • Internet Access
  • A/C or climate control
  • Grill
  • Linens Provided
  • Microwave
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(8)

Walk to everywhere, but feels very private .

Left on Nov 30, 2013 for a stay in November 2013

My family including our havanese puppy (Reggie)just finished a great week stay in key west. Casa Margarita is within a hundred yards of every restaurant of the harbor .Many places are within crawling distance like harpoon harry's,( 3 doors down)or Pepe's (6 doors down).

You wont hear any noise even the traffic out front is quiet as its on a quiet street ( margaret ave )in a residential …

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$198

2 BR / 2 BA / Sleeps 6

1 / 26

$198

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RUM CAY SUITE #304 - 2/2 Condo w/ Pool & Hot Tub - Near Smathers Beach

Key West condo
2 BR / 2 BA / Sleeps 6 | Quick view

Details

Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$188

1 BR / 1 BA / Sleeps 4

1 / 27

$188

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"POOLSIDE RETREAT" - 1 Block To Duval St. - Shared Pool

Key West house
1 BR / 1 BA / Sleeps 4 | Quick view

Details

Part of POOLSIDE PARADISE One-half block off world famous Duval Street sits the beautifully renovated home in the 500 block of Olivia Street. The updated kitchen features granite counter tops and beautiful wooden floors. Your bathroom offers a large walk-in tiled shower. A semi-private pool with waterfall feature(…
  • 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

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$198

2 BR / 2 BA / Sleeps 6

1 / 34

$198

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MARTINIQUE SUITE #108 - 2/2 Condo w/ Pool & Hot Tub - Sunset View!

Key West condo
2 BR / 2 BA / Sleeps 6 | Quick view

Details

Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$188

1 BR / 1 BA / Sleeps 4

3 Reviews

$188

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HIDEAWAY @ TROPICAL VILLAGE - Cozy Condo For 2 w/ Shared Pool

Key West cottage
1 BR / 1 BA / Sleeps 4 | Quick view
“ Excellent ” 3 Reviews

Details

Reviews

(3)

Part of TROPICAL VILLAGE Tropical Hideaway - Lush gardens surround this lovingly restored two-story vacation house. This downstairs rental cottage has one bedroom with full bath and features a living room with queen sleeper-sofa, cable TV, DVD, stereo with CD player, and wireless internet. The bedroom has a queen …
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(3)

Great stay!!!

Left on Oct 08, 2014 for a stay in October 2014

Everything was great! The location was perfect - and the private hot tub was the best! Only down side (which wasn't a big deal) was there were ants on the kitchen counter!

Very nice rental!!!!

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$90

2 BR / 3 BA / Sleeps 4

1 / 24

$90

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Green Orchid

Key West house
2 BR / 3 BA / Sleeps 4 | Quick view

Details

GREEN ORCHID: Situated on a narrow lane in one of the last historic Old Town neighborhood, this 2-bedroom 2.5 bath home has it all!Living room has French doors opening to let in the tropical breezes. Modern, stainless kitchen. Outdoor shower on the lushly landscaped walkway. Guest bedroom with full size bed has …
  • Internet Access
  • A/C or climate control
  • Parking
  • Television
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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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

Key West house
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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$198

2 BR / 2 BA / Sleeps 6

1 Reviews

$198

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BARBADOS SUITE #204 - 2/2 Condo w/ Pool & Hot Tub - Near Smathers Beach

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

Details

Reviews

(1)

Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped …
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Fitness Room
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Excellent Accomodations

Left on Apr 29, 2015 for a stay in April 2015

We came in a small plane, so we needed to ship our luggage down to Key West. The office staff allowed us to ship it right to the check in office. The suite had two rooms and a kitchen, with a beautiful view of the marsh between the suite and the Airport. The suite was well furnished and had plenty of room. It was also a clean room with ice cold ac. We were also allowed to plug our electric rental…

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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

Key West house
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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$198

2 BR / 2 BA / Sleeps 6

1 Reviews

$198

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SALT CAY SUITE #410 - 2/2 Condo w/ Pool & Hot Tub - Near Smathers Beach

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

Details

Reviews

(1)

Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

shady balcony in the morning

Left on Nov 11, 2014 for a stay in October 2014

We had a great night at sunrise suites. It is not central, so you have to get a taxy to go downtown. Because you have a sunset drink, wine with dinner and one before going back.

The rooms are good and comfortable, the kitchen has what you need.

by the way the lobby was friendly

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$268

2 BR / 3 BA / Sleeps 6

15 Reviews

$268

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"CASA HAVANA @ DUVAL SQUARE" 2-Story Condo On Duval St w/ Pvt Hot Tub

Key West condo
2 BR / 3 BA / Sleeps 6 | Quick view
“ Excellent ” 15 Reviews

Details

Reviews

(15)

This spacious unit is only steps from a large pool and covered gazebo. On the ground floor is a secured garage for parking your vehicle. Lush and tropical gardens surround this beautiful development in the heart of historic Old Town. Private, secured parking beneath the complex and security entrances gives the …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(15)

awesome

Left on Jun 24, 2009 for a stay in April 2008

we really enjoyed our stay. the rental unit was more than we anticipated. the pool was nice and we were within walking distance to most everything we wanted to do.

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$138

4294967295 BR / 1 BA / Sleeps 2

1 Reviews

$138

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"DECKSIDE SUITE" Studio w/ Shared Hot Tub Steps To Duval St

Key West cottage
1 BA / Sleeps 2 | Quick view
“ Terrible ” 1 Reviews

Details

Reviews

(1)

Part of Conch Republic Cottages Efficiency at its finest! The Deckside Suite is the perfect vacation rental in Key West for those who are trying to get the most bang for their buck. You have everything you need in this cozy, studio-style unit, including a fully-stocked kitchen, cable TV, free wireless internet, and a…
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

Rats Rats and Rats

Left on Jan 21, 2015 for a stay in January 2015

this is a very small unit... in need of a total make over. and yes there are rats all over the deck and in the walls. We could hear them at night and in the moring we saw 4 run across the deck.... Management (Key West Vacation Rentas)was not concerned simply saying there are rats everwhere in Key West.. It appears that one side of the unit is rented to locals and they helped entertain us by …

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$268

2 BR / 3 BA / Sleeps 6

23 Reviews

$268

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"CASA CUBANA @ DUVAL SQUARE" Luxurious Condo w/ Pvt Parking & Shared Pool

Key West condo
2 BR / 3 BA / Sleeps 6 | Quick view
“ Excellent ” 23 Reviews

Details

Reviews

(23)

Lush and tropical gardens surround this beautiful development in the heart of historic Old Town. Private, secured parking beneath the complex and security entrances gives the feeling of exclusivity unparalleled in Key West. The foyer of this Mediterranean Style unit with Mexican Tile downstairs and oak floors …
  • 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

Details

Reviews

(23)

Don't you think it's a little late?

Left on Jun 24, 2009 for a stay in November 2007

To ask for a review a year & a half after our stay?

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$198

2 BR / 2 BA / Sleeps 6

1 / 24

$198

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TIERRA BOMBA SUITE #403 - 2/2 Condo w/ Pool & Hot Tub - Near Smathers Beach

Key West condo
2 BR / 2 BA / Sleeps 6 | Quick view

Details

Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Pet friendly
  • Suitable for children - ask
  • 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

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

Details

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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$198

2 BR / 2 BA / Sleeps 6

1 / 24

$198

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CURACAO SUITE #202 - 2/2 Condo w/ Pool & Hot Tub - Near Smathers Beach

Key West condo
2 BR / 2 BA / Sleeps 6 | Quick view

Details

Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
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