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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

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