Key West Vacation Rentals for Groups, Reunions, and Family Gatherings

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Key West Vacation Rental Groups

Quite often, one vacation rental home may not suit you needs. You may be planning a family reunion in Key West, a business meeting or conference, or just a large group of friends deciding to vacation together on our wonderful island. To help with your planning, we have grouped our vacation homes, condos, and suites that are near one another on this page.
For a list of all our vacation rentals, go to our Key West Hideaways Page.
There are 3 "Seasons" for rates:
Winter/Spring: December 15 to April 30
Summer/Fall: June 1 to December 14 (Except Nov.)
Shoulder Months: May and November
Higher Rates apply for Holiday Periods and/or Special Events.
View Availibilty Chart for all our Rentals
 Key to Amenities Icons:
Full Kitchen=Full Kitchen   Kitchenette=Kitchenette  
Heated Swimming Pool=Heated Pool   Whirlpool Spa=Whirlpool Spa Hi-Speed Internet=Hi Speed Internet  
Parking=Parking   Limited Parking=Limited Parking   Beach Pass=Beach Pass

Pirate's Cove and
Island Hideaways


Pirate's Cove
Cottage Guest Suites

Read about Pirate's Cove


Crow's Nest Key West Vacation Cottage Suite
Crow's Nest
at Pirate's Cove
(Vacation Suite)
614 Green Street
Key West, FL
Living Room / 1 Bdrm. / 1 Bath
Accommodates 2 People
$198 to $298
Locate on Yahoo Maps
Crow's Nest Availability
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Hi-Speed Internet Heated Swimming Pool
Captain's Quarters Key West Vacation Cottage Suite
Captain's Quarters
at Pirate's Cove
(Cottage Suite)
614 Green Street
Key West, FL
Living Room / 2 Bdrms. / 1 Bath
Accommodates 2 to 4 People
$268 to $368
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Captain's Quarters Availability
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Hi-Speed Internet Heated Swimming Pool



 

Island Hideaways
Homes, Cottages, and Suites

Read about Island Hideaways

Island Oasis, an Island Hideaways Vacation Home
Island Oasis
an Island Hideaway
(Vacation Home)
729 Whitehead Street
Key West, FL
3 Bedrooms / 2 Baths
Accommodates 6 People
$408 to $508
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Island Oasis Availability
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Hi-Speed Internet Full Kitchen Heated Swimming Pool
Palm Isle, an Island Hideaways Vacation Studio
Palm Isle
an Island Hideaway
(Vacation Studio)
729 Whitehead Street
Key West, FL
1 Bedroom-Sittingroom / 1 Bath
Accommodates up to 4 People
$168 to $268
Locate on Yahoo Maps
Palm Isle Availability
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Kitchenette Whirlpool Spa Beach Pass
Little Palm, an Island Hideaways Vacation Studio
Little Palm
an Island Hideaway
(Cottage Studio)
729 Whitehead Street
Key West, FL
1 Bedroom / 1 Bath
Accommodates only 2 People
$198 to $298
Locate on Yahoo Maps
Little Palm Availability
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Kitchenette Whirlpool Spa Beach Pass

The Sanctuary
Vacation Studios

Read about The Santuary


The Egret Studio at The Sanctuary
The Egret Studio
at The Sanctuary
(Studio)
1330 Simonton Street
Key West, FL
1 Bedroom. / 1 Bath
Accommodates 2 to 4 People
$158 to $238
Locate on Yahoo Maps
The Egret Studio Availability
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Kitchenette Whirlpool Spa
The Heron Studio at The Sanctuary
The Heron Studio
at The Sanctuary
(Studio)
1330 Simonton Street
Key West, FL
1 Bedroom-Sittingroom / 1 Bath
Accommodates 2 to 4 People
$158 to $238
Locate on Yahoo Maps
The Heron Studio Availability
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Kitchenette Whirlpool Spa
The Ibis Studio at The Sanctuary
The Ibis Studio
at The Sanctuary
(Studio)
1330 Simonton Street
Key West, FL
1 Bedroom. / 1 Bath
Accommodates 2 to 4 People
$158 to $238
Locate on Yahoo Maps
The Ibis Studio Availability
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Kitchenette Whirlpool Spa
The Osprey Studio at The Sanctuary
The Osprey Studio
at The Sanctuary
(Studio)
1330 Simonton Street
Key West, FL
1 Bedroom-Sittingroom / 1 Bath
Accommodates 2 to 4 People
$158 to $238
Locate on Yahoo Maps
The Osprey Studio Availability
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Kitchenette Whirlpool Spa
The Pelican Studio at The Sanctuary
The Pelican Studio
at The Sanctuary
(Studio)
1330 Simonton Street
Key West, FL
1 Bedroom-Sittingroom / 1 Bath
Accommodates 2 to 4 People
$158 to $238
Locate on Yahoo Maps
The Pelican Studio Availability
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Kitchenette Whirlpool Spa
The Seagull Studio at The Sanctuary
The Seagull Studio
at The Sanctuary
(Studio)
1330 Simonton Street
Key West, FL
1 Bedroom / 1 Bath
Accommodates 2 to 4 People
$158 to $238
Locate on Yahoo Maps
The Seagull Studio Availability
Click to Close.

Kitchenette Whirlpool Spa

Tropical Village
Suites, Cottages, and Homes

Read about Tropical Village


Poolside Paradise in Tropical Village
Poolside Paradise
in Tropical Village
(Cottage Studio)
708½ South Street
Key West, FL
1 Bedroom / 1 Bath
Accommodates 2 People
$158 to $238
Locate on Yahoo Maps
Poolside Paradise Availability
Click to Close.

Hi-Speed Internet Heated Swimming Pool Kitchenette
Tropical Hideaway in Tropical Village
Tropical Hideaway
in Tropical Village
(Suite)
706 South Street
Key West, FL
Livingroom / 1 Bdrm. / 1 Bath
Accommodates 2 to 4 People
$198 to $298
Locate on Yahoo Maps
Tropical Hideaway Availability
Click to Close.

Hi-Speed Internet Full Kitchen Heated Pool Whirlpool Spa
Tropical Retreat in Tropical Village
Tropical Retreat
in Tropical Village
(Home)
706 South Street
Key West, FL
Livingroom / 2 Bedrooms / 1 Bath
Accommodates 4 People
$198 to $298
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Tropical Retreat Availability
Click to Close.

Hi-Speed Internet Heated Swimming Pool Full Kitchen
Tropical Village Cottage in Tropical Village
Tropical Village Cottage
in Tropical Village
(Home)
708 South Street
Key West, FL
Livingroom / 2 Bedrooms / 2 Baths
Accommodates up to 5 People
$258 to $358
Locate on Yahoo Maps
Tropical Village Cottage Availability
Click to Close.

Hi-Speed Internet Heated Swimming Pool Full Kitchen
Southern Cross in Tropical Village
Southern Cross
in Tropical Village
(Home)
1400-B Alberta Street
Key West, FL
Livingroom / 2 Bedrooms / 2 Baths
Accommodates up to 6 People
$258 to $358
Locate on Yahoo Maps
Southern Cross Availability
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Hi-Speed Internet Heated Swimming Pool Full Kitchen
Toon Hall in Tropical Village
Toon Hall
in Tropical Village
(Home)
1400-A Alberta Street
Key West, FL
Livingroom / 3 Bedrooms / 2 Baths
Accommodates up to 8 People
$348 to $448
Locate on Yahoo Maps
Toon Hall Availability
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Hi-Speed Internet Full Kitchen Heated Swimming Pool Whirlpool Spa

Pelican Landing
Waterfront Condominiums
with Boat Slips
Read about Pelican Landing


Abaco Suite and Retreat at Pelican Landing
Abaco
at Pelican Landing
(Waterfront Condominium)
915 Eisenhower Drive
Key West, FL
1 Bedroom Suite
Accommodates 2 People
$198 to $298
2 Bedroom / 2 Bath Retreat
Accommodates 6 People
$288 to $388
Locate on Yahoo Maps
Abaco Availability
Click to Close.

Hi-Speed Internet Full Kitchen Heated Pool Parking
Andros Suite and Retreat at Pelican Landing
Andros
at Pelican Landing
(Waterfront Condominium)
915 Eisenhower Drive
Key West, FL
1 Bedroom Suite
Accommodates 2-4 People
$198 to $298
2 Bedroom / 2 Bath Retreat
Accommodates 6 People
$288 to $388
Locate on Yahoo Maps
Andros Availability
Click to Close.

Hi-Speed Internet Full Kitchen Heated Pool Parking
Antigua Suite and Retreat at Pelican Landing
Antigua
at Pelican Landing
(Waterfront Condominium)
915 Eisenhower Drive
Key West, FL
1 Bedroom Suite
Accommodates 2 People
$198 to $298
2 Bedroom / 2 Bath Retreat
Accommodates 6 People
$288 to $388
Locate on Yahoo Maps
Antigua Availability
Click to Close.

Hi-Speed Internet Full Kitchen Heated Pool Parking
Aruba Suite and Retreat at Pelican Landing
Aruba
at Pelican Landing
(Waterfront Condominium)
915 Eisenhower Drive
Key West, FL
1 Bedroom Suite
Accommodates 2 People
$198 to $298
2 Bedroom / 2 Bath Retreat
Accommodates 6 People
$288 to $388
Locate on Yahoo Maps
Aruba Availability
Click to Close.

Hi-Speed Internet Full Kitchen Heated Pool Parking
Bermuda Suite and Retreat at Pelican Landing
Bermuda
at Pelican Landing
(Waterfront Condominium)
915 Eisenhower Drive
Key West, FL
1 Bedroom Suite
Accommodates 2 People
$198 to $298
2 Bedroom / 2 Bath Retreat
Accommodates 6 People
$288 to $388
Locate on Yahoo Maps
Bermuda Availability
Click to Close.

Hi-Speed Internet Full Kitchen Heated Pool Parking
Bonaire Suite and Retreat at Pelican Landing
Bonaire
at Pelican Landing
(Waterfront Condominium)
915 Eisenhower Drive
Key West, FL
1 Bedroom Suite
Accommodates 2 People
$198 to $298
2 Bedroom / 2 Bath Retreat
Accommodates 6 People
$288 to $388
Locate on Yahoo Maps
Bonaire Availability
Click to Close.

Hi-Speed Internet Full Kitchen Heated Pool Parking
Curaçao Suite and Retreat at Pelican Landing
Curaçao
at Pelican Landing
(Waterfront Condominium)
915 Eisenhower Drive
Key West, FL
1 Bedroom Suite
Accommodates 2 People
$198 to $298
2 Bedroom / 2 Bath Retreat
Accommodates 6 People
$288 to $388
Locate on Yahoo Maps
Curaçao Availability
Click to Close.

Hi-Speed Internet Full Kitchen Heated Pool Parking
Dominica Suite and Retreat at Pelican Landing
Dominica
at Pelican Landing
(Waterfront Condominium)
915 Eisenhower Drive
Key West, FL
1 Bedroom Suite
Accommodates 2 People
$198 to $298
2 Bedroom / 2 Bath Retreat
Accommodates 6 People
$288 to $388
Locate on Yahoo Maps
Dominica Availability
Click to Close.

Hi-Speed Internet Full Kitchen Heated Pool Parking
Eleuthera Suite and Retreat at Pelican Landing
Eleuthera
at Pelican Landing
(Waterfront Condominium)
915 Eisenhower Drive
Key West, FL
1 Bedroom Suite
Accommodates 2 People
$198 to $298
2 Bedroom / 2 Bath Retreat
Accommodates 6 People
$288 to $388
Locate on Yahoo Maps
Eleuthera Availability
Click to Close.

Hi-Speed Internet Full Kitchen Heated Pool Parking
Flamingo Suite and Retreat at Pelican Landing
Flamingo
at Pelican Landing
(Waterfront Condominium)
915 Eisenhower Drive
Key West, FL
1 Bedroom Suite
Accommodates 2 People
$198 to $298
2 Bedroom / 2 Bath Retreat
Accommodates 6 People
$288 to $388
Locate on Yahoo Maps
Flamingo Availability
Click to Close.

Hi-Speed Internet Full Kitchen Heated Pool Parking
Florida Suite and Retreat at Pelican Landing
Florida
at Pelican Landing
(Waterfront Condominium)
915 Eisenhower Drive
Key West, FL
1 Bedroom Suite
Accommodates 2 People
$198 to $298
2 Bedroom / 2 Bath Retreat
Accommodates 6 People
$288 to $388
Locate on Yahoo Maps
Florida Availability
Click to Close.

Hi-Speed Internet Full Kitchen Heated Pool Parking
Harbour Island Suite and Retreat at Pelican Landing
Harbour Island
at Pelican Landing
(Waterfront Condominium)
915 Eisenhower Drive
Key West, FL
1 Bedroom Suite
Accommodates 2 People
$198 to $298
2 Bedroom / 2 Bath Retreat
Accommodates 6 People
$288 to $388
Locate on Yahoo Maps
Harbour Island Availability
Click to Close.

Hi-Speed Internet Full Kitchen Heated Pool Parking
St. John Penthouse at Pelican Landing
St. John Penthouse
at Pelican Landing
(Waterfront Penthouse)
915 Eisenhower Drive
Key West, FL
3 Bedrooms / 3 Baths
Accommodates 6 to 10 People
$348 to $448
Locate on Yahoo Maps
St. John Penthouse Availability
Click to Close.

Hi-Speed Internet Full Kitchen Heated Pool Parking
St. Kitts Penthouse at Pelican Landing
St. Kitts Penthouse
at Pelican Landing
(Waterfront Penthouse)
915 Eisenhower Drive
Key West, FL
3 Bedrooms / 3 Baths
Accommodates 6 to 10 People
$348 to $448
Locate on Yahoo Maps
St. Kitts Penthouse Availability
Click to Close.

Hi-Speed Internet Full Kitchen Heated Pool Parking
St. Croix Penthouse at Pelican Landing
St. Croix Penthouse
at Pelican Landing
(Waterfront Penthouse)
915 Eisenhower Drive
Key West, FL
4 Bedrooms / 4 Baths
Accommodates 8 to 12 People
$448 to $548
Locate on Yahoo Maps
St. Croix Penthouse Availability
Click to Close.

Hi-Speed Internet Full Kitchen Heated Pool Parking
St. Thomas Penthouse at Pelican Landing
St. Thomas Penthouse
at Pelican Landing
(Waterfront Penthouse)
915 Eisenhower Drive
Key West, FL
4 Bedrooms / 4 Baths
Accommodates 8 to 12 People
$448 to $548
Locate on Yahoo Maps
St. Thomas Penthouse Availability
Click to Close.

Hi-Speed Internet Full Kitchen Heated Pool Parking

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