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Key West Vacation Rentals

Find the best deals on 1,461 vacation rentals in Key West

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Top rentals in Key West

Find the perfect Key West vacation rental for your needs
Galleria Condominiums
Galleria Condominiums
6.8
$243
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Pescado Penthouse On Duval
Pescado Penthouse On Duval
8.7
$272
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Gorgeous Condo W/ Scenic Views, Shared Pool & Hot Tub, Balcony, & Parking!
Gorgeous Condo W/ Scenic Views, Shared Pool & Hot Tub, Balcony, & Parking!
9.3
$317
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Cozy, Dog-Friendly Suite - 2 Blocks From Main Drag!
Cozy, Dog-Friendly Suite - 2 Blocks From Main Drag!
8.2
$191
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Key West Villas
Key West Villas
9.0
$280
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Colors On White
Colors On White
7.4
$185
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Simonton Court Cottages
Simonton Court Cottages
6.8
$196
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The Green House - Sunset
The Green House - Sunset
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Banana's Foster Guesthouse
Banana's Foster Guesthouse
8.3
$246
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Paradise Place (Condo)
Paradise Place (Condo)
7.5
$428
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' A Love Shack in the Heart of Old Town Key West Florida!'
' A Love Shack in the Heart of Old Town Key West Florida!'
$129
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Luxurious Historic House With Pool In Old Town 1 Introductory Rates!
Luxurious Historic House With Pool In Old Town 1 Introductory Rates!
8.9
$448
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Newly furnished suite w/ shared pool & hot tub, tennis, balcony, parking, dog ok
Newly furnished suite w/ shared pool & hot tub, tennis, balcony, parking, dog ok
8.9
$313
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The Island Suite
The Island Suite
10.0
$436
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Canal View Condo in Skip Jack Resort W/ Cabana Club Membership Included
Canal View Condo in Skip Jack Resort W/ Cabana Club Membership Included
$210
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Duval Corner
Duval Corner
6.3
$330
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Pet Friendly 2/2. 4 Free Bikes. New Renovation, Heated Pool 2 Blocks To Duval St
Pet Friendly 2/2. 4 Free Bikes. New Renovation, Heated Pool 2 Blocks To Duval St
9.5
$322
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Cozy, Dog-Friendly Suite With Balcony, Shared Hot Tub/Pool, And Private Parking!
Cozy, Dog-Friendly Suite With Balcony, Shared Hot Tub/Pool, And Private Parking!
8.9
$319
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Cozy condo with free WiFi & fantastic location in central Key West
Cozy condo with free WiFi & fantastic location in central Key West
9.7
$313
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Kimpton Ella's Cottages, an IHG Hotel
Kimpton Ella's Cottages, an IHG Hotel
8.9
$450
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Real World Mtv House---Not Just A House Your Own Private Resort
Real World Mtv House---Not Just A House Your Own Private Resort
9.2
$2,876
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Studio condo w/ entertainment, full kitchen & private parking - central location
Studio condo w/ entertainment, full kitchen & private parking - central location
9.3
$241
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Sunrise Suites Cozumel Suite #112
Sunrise Suites Cozumel Suite #112
8.0
$315
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Sunny condo w/ shared pool & entertainment - central location
Sunny condo w/ shared pool & entertainment - central location
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Dog-Friendly Studio - Within Walking Distance To Duval Street!
Dog-Friendly Studio - Within Walking Distance To Duval Street!
8.4
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Family-Friendly W/Pool & Hot Tub, Ideal For Exploring Key West - 1 Dog Welcome!
Family-Friendly W/Pool & Hot Tub, Ideal For Exploring Key West - 1 Dog Welcome!
8.1
$347
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Heart Of Old Town Getaway, Perfect Romantic Retreat -Near The Action
Heart Of Old Town Getaway, Perfect Romantic Retreat -Near The Action
8.4
$250
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Dog-friendly studio in historic building w/ shared pool - beach nearby
Dog-friendly studio in historic building w/ shared pool - beach nearby
9.3
$231
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'la Dolce Vita' Old Town, Steps To Duval! Sleeps 2-4, 3 Blocks To South Beach!
'la Dolce Vita' Old Town, Steps To Duval! Sleeps 2-4, 3 Blocks To South Beach!
8.8
$322
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Tropical condo for two with a great location in the heart of Old Town Key West
Tropical condo for two with a great location in the heart of Old Town Key West
7.5
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Breezy condo w/ shared pool & hot tub, private parking & great location - dog OK
Breezy condo w/ shared pool & hot tub, private parking & great location - dog OK
9.5
$315
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Charming tropical getaway w/ shared pool, sundeck, and bar - near Duval Street
Charming tropical getaway w/ shared pool, sundeck, and bar - near Duval Street
9.3
$314
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Sunny condo w/ entertainment, balcony, & great location near the beach! Dogs OK!
Sunny condo w/ entertainment, balcony, & great location near the beach! Dogs OK!
9.3
$322
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Quiet, Quaint, And Conveniently Located! New Pool!
Quiet, Quaint, And Conveniently Located! New Pool!
8.8
$172
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Contemporary dog-friendly cottage with easy beach access and shared pool
Contemporary dog-friendly cottage with easy beach access and shared pool
9.2
$278
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Oceanfront
Oceanfront
9.8
$547
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Dream Vacation in the keys
Dream Vacation in the keys
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~ Solaris Cottage ~ Enjoy Old Town Livin'. Dog Friendly Home!
~ Solaris Cottage ~ Enjoy Old Town Livin'. Dog Friendly Home!
9.9
$342
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Galleon Resort Waterfront Luxury In Old Town Key West
Galleon Resort Waterfront Luxury In Old Town Key West
10.0
$440
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Two-level dog-friendly cottage w/shared pool, outdoor shower - near the beach
Two-level dog-friendly cottage w/shared pool, outdoor shower - near the beach
9.6
$265
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Shared Pool, Hot Tub, Tennis Courts, & Balcony - Dogs Ok! Family Friendly!
Shared Pool, Hot Tub, Tennis Courts, & Balcony - Dogs Ok! Family Friendly!
9.3
$452
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Secluded, Private, Tropical Retreat In Old Town, Key West.
Secluded, Private, Tropical Retreat In Old Town, Key West.
9.2
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Relax On Historic Inn's Top Floor - Shared Pool & Semi-Private Deck!
Relax On Historic Inn's Top Floor - Shared Pool & Semi-Private Deck!
8.3
$244
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Turn Lemons Into Lemonade Jan. Feb. & March. Prices Lowest Ever!
Turn Lemons Into Lemonade Jan. Feb. & March. Prices Lowest Ever!
9.1
$180
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Palm Island Suite at Top Of Duval
Palm Island Suite at Top Of Duval
9.3
$267
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Comfy, Dog-Friendly Retreat W/ Shared Hot Tubs, Patio, Great Old Town Location
Comfy, Dog-Friendly Retreat W/ Shared Hot Tubs, Patio, Great Old Town Location
8.8
$230
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New! Oct Special! Waterfront Penthouse. 10-15 Minute Drive To Downtown Kyw
New! Oct Special! Waterfront Penthouse. 10-15 Minute Drive To Downtown Kyw
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Hemingway Hideaway in Truman Annex
Hemingway Hideaway in Truman Annex
9.4
$450
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Family House- Two K bedrooms, 1.5 baths, Pvt.Spa in Garden Setting-Shared Pools
Family House- Two K bedrooms, 1.5 baths, Pvt.Spa in Garden Setting-Shared Pools
10.0
$527
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Family Friendly Condo W/ Shared Pool, Hot Tub & Dogs Ok!
Family Friendly Condo W/ Shared Pool, Hot Tub & Dogs Ok!
8.8
$334
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East-facing Sunrise Suites condo w/shared pool, hot tub, tennis, private balcony
East-facing Sunrise Suites condo w/shared pool, hot tub, tennis, private balcony
8.7
$317
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Dog-friendly Sunrise Suites condo w/ shared pool, hot tub & free parking
Dog-friendly Sunrise Suites condo w/ shared pool, hot tub & free parking
9.2
$345
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Royal Poinciana in the Truman Annex
Royal Poinciana in the Truman Annex
10.0
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Dog-friendly studio condo w/ deck & free WiFi, in the heart of Old Town Key West
Dog-friendly studio condo w/ deck & free WiFi, in the heart of Old Town Key West
8.2
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Dog-Friendly Condo W/ Shared Pool, Hot Tub, & More! Walk/Bike To Beach!
Dog-Friendly Condo W/ Shared Pool, Hot Tub, & More! Walk/Bike To Beach!
8.8
$391
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Breezy Bungalow (Townhouse)
Breezy Bungalow (Townhouse)
9.4
$466
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Passover Cottage
Passover Cottage
9.9
$771
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Kate's Krawl By Duval
Kate's Krawl By Duval
9.0
$393
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New Casa Solis With Scenic Views and 30' Dock.
New Casa Solis With Scenic Views and 30' Dock.
9.5
$251
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Comfortably Elegant Moon Bay Condo With Boat Slip
Comfortably Elegant Moon Bay Condo With Boat Slip
$256
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Key West On My Mind: 2 Br, 2 Ba Condominium In Key West, Sleeps 6
Key West On My Mind: 2 Br, 2 Ba Condominium In Key West, Sleeps 6
8.8
$665
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Somewhere On The Beach: 2 Br, 2 Ba Condominium In Key West, Sleeps 6
Somewhere On The Beach: 2 Br, 2 Ba Condominium In Key West, Sleeps 6
9.1
$688
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Tropical Garden Oasis - Treetop Cottage
Tropical Garden Oasis - Treetop Cottage
$186
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Duval Penthouse
Duval Penthouse
9.7
$769
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Poolside Retreat
Poolside Retreat
7.9
$311
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Fiesta Key Rv Resort Standard Room 2
Fiesta Key Rv Resort Standard Room 2
8.3
$332
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Southernmost Sanctuary Apartment
Southernmost Sanctuary Apartment
7.9
$255
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Palm Gardens
Palm Gardens
8.1
$329
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Old Town Suites
Old Town Suites
8.7
$375
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Key West Harbour Oceanfront Suites
Key West Harbour Oceanfront Suites
$606
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Conch Cottages of Villas Key West
Conch Cottages of Villas Key West
9.0
$990
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Papa's Hideaway
Papa's Hideaway
8.3
$339
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Gated Community On Open Water With Dock, Heated Pool, Kayaks, Bikes
Gated Community On Open Water With Dock, Heated Pool, Kayaks, Bikes
9.9
$435
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Cozy, dog-friendly condo with views - walk to beach, dining, & attractions
Cozy, dog-friendly condo with views - walk to beach, dining, & attractions
8.6
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Treasure Trove at Coral Hammock
Treasure Trove at Coral Hammock
$406
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Skipjack #407 ~ 1 bed 1 bath Condo ~ Nightly
Skipjack #407 ~ 1 bed 1 bath Condo ~ Nightly
7.4
$198
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Private Beach-Large Pool-Walking Distance:Dining/Fishing/Golf
Private Beach-Large Pool-Walking Distance:Dining/Fishing/Golf
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Nautical Keys Suite at Top Of Duval
Nautical Keys Suite at Top Of Duval
9.6
$267
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Fleming-O Quiet Retreat In The Heart Of Old Town Key West- Low September Rate
Fleming-O Quiet Retreat In The Heart Of Old Town Key West- Low September Rate
9.9
$464
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Key Largo - Kawama Tower - Ocean View
Key Largo - Kawama Tower - Ocean View
9.6
$258
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'in Good Spirits'~waterfront Condo W/Wrap-Around Balcony & Community Pool!
'in Good Spirits'~waterfront Condo W/Wrap-Around Balcony & Community Pool!
9.6
$580
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Dog-friendly studio in the heart of Old Town - walk to beach & attractions!
Dog-friendly studio in the heart of Old Town - walk to beach & attractions!
7.7
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Downtown Cottage Just Off Famous Duval Street-No Contact Check-In
Downtown Cottage Just Off Famous Duval Street-No Contact Check-In
9.7
$448
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Beautifully restored large Conch home downtown
Beautifully restored large Conch home downtown
$257
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Casa Cay West Beautiful Tropical House 3 Bedrooms 2 King Suites Pool
Casa Cay West Beautiful Tropical House 3 Bedrooms 2 King Suites Pool
9.9
$535
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Waterfront Fun And Funky , Newly Renovated Beautiful Duck Key Condo
Waterfront Fun And Funky , Newly Renovated Beautiful Duck Key Condo
9.7
$377
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Almost Southernmost
Almost Southernmost
8.0
$381
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Cozy condo 1 bed/1 bath
Cozy condo 1 bed/1 bath
$191
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Seaside Townhouse Ocean Views
Seaside Townhouse Ocean Views
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When to book a vacation apartment in Key West

Check out the tips below to find the best deal on a Key West vacation rental property
Low Season
September
High Season
April

cheapest month to stay

40%

expected price decrease

most expensive time to stay

21%

expected price increase

Price
$192 - $397

Cheapest vacation rentals in Key West

Our lowest priced vacation apartments and property rentals for a cheaper way to stay in Key West
Colors On White
Colors On White
7.4
$185
Southernmost Sanctuary Apartment
Southernmost Sanctuary Apartment
7.9
$255
Simonton Court Cottages
Simonton Court Cottages
6.8
$196
Pescado Penthouse On Duval
Pescado Penthouse On Duval
8.7
$272
Banana's Foster Guesthouse
Banana's Foster Guesthouse
8.3
$246
Key West Villas
Key West Villas
9.0
$280

Key West vacation apartments & rental properties FAQ

How long do people typically book vacation apartments for in Key West?

3 nights is the typical length of a Key West vacation rental booking.

How much does a vacation rental apartment in Key West cost?

Renting a vacation apartment in Key West will see a range in pricing typically determined by the season, location of the apartment and the number of rooms required. Recently, a typical search for apartment rentals in Key West suggests an average of $329 per night.

When is the best time to book a vacation rental in Key West?

Key West vacation rentals are at their cheapest in September. Rental prices can be around 40% lower per night than in the high season.

What’s the best area of Key West to book a vacation rental in?

New Town, Truman Annex, and Casa Marina are typically the most popular places to rent vacation apartments in Key West.


momondo's favorite rental properties

Learn more about these user-preferred vacation homes in Key West, United States
Hotel deals North America United States Florida Key West Vacation Rentals in Key West