Key West Vacation Rentals

Find the best deals on 1,466 vacation rentals in Key West

Top rentals in Key West

Find the perfect Key West vacation rental for your needs

Galleria Condominiums

6.8

$235

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Pescado Penthouse On Duval

8.8

$289

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Dog-friendly condo w/ scenic views, shared pool & hot tub, balcony & parking

9.4

$305

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Colors on White

7.5

$133

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Simonton Court Cottages

6.8

$226

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Key West Villas

8.9

$167

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Banana's Foster Guesthouse

8.0

$257

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Paradise Place (Condo)

$278

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Pet Friendly 2/2. 4 Free Bikes New Renovation,heated Pool 2 Blocks To Duval St

9.1

$247

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Studio condo w/ entertainment, full kitchen & private parking - central location

9.5

$250

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Cozy condo with free WiFi & fantastic location in central Key West

9.8

$322

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Cozy, dog-friendly suite with balcony, shared hot tub/pool, and private parking

8.6

$267

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Newly furnished suite w/ shared pool & hot tub, tennis, balcony, parking, dog ok

8.9

$263

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Real World Mtv House---Not Just A House Your Own Private Resort

9.2

$2,683

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Luxurious Historic House With Pool In Old Town 1 Introductory Rates!

9.2

$401

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Heart Of Old Town Getaway, Perfect Romantic Retreat -Near The Action

8.5

$255

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Family-friendly w/ pool & hot tub perfect for exploring Key West! Dogs welcome!

8.5

$302

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Kimpton Ella's Cottages

9.1

$229

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Sunrise Suites Cozumel Suite #112

8.3

$269

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The Island Suite

10.0

$262

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Duval Corner

7.0

$301

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Cozy, dog-friendly retreat w/ shared hot tubs, patio, great location in Old Town

8.8

$246

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Contemporary dog-friendly cottage with easy beach access and shared pool

9.7

$315

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Breezy condo w/ shared pool & hot tub, private parking & great location - dog OK

9.7

$304

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Charming tropical getaway w/ shared pool, sundeck, and bar - near Duval Street

9.1

$315

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'la Dolce Vita' Old Town, Steps To Duval! Sleeps 2-4, 3 Blocks To South Beach!

8.8

$290

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Hemingway Hideaway in Truman Annex

9.0

$432

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Galleon Resort Waterfront Luxury In Old Town Key West

9.0

$446

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Two-level dog-friendly cottage w/shared pool, outdoor shower - near the beach

9.1

$320

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Shared pool, hot tub, tennis courts, & balcony - dogs OK Family friendly

9.5

$255

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Relax on historic inn's top floor - shared pool & semi-private deck

8.3

$262

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Tired Of Being Inside! Ask About Our November Specials

8.5

$182

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Palm Island Suite at Top Of Duval

9.1

$266

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Oceanfront

9.8

$544

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Dog-Friendly Condo W/ Shared Pool, Hot Tub, & More! Walk/Bike To Beach!

8.8

$319

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Family House- Two K bedrooms, 1.5 baths, Pvt.Spa in Garden Setting-Shared Pools

10.0

$492

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Family friendly condo w/ shared pool, hot tub, & complimentary shuttle Dogs ok

9.2

$263

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East-facing Sunrise Suites condo w/shared pool, hot tub, tennis, private balcony

8.5

$270

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Dog-friendly Sunrise Suites condo w/ shared pool, hot tub & free parking

9.3

$331

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Dog-friendly studio in historic building w/ shared pool - beach nearby

9.1

$226

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~ Solaris Cottage ~ Enjoy Old Town Livin'. Dog Friendly Home!

8.6

$281

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Sunny condo w/ entertainment, balcony, & great location near the beach! Dogs OK!

9.8

$337

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Quiet, Quaint, And Conveniently Located! New Pool!

8.8

$177

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Key West On My Mind: 2 Br, 2 Ba Condominium In Key West, Sleeps 6

8.7

$442

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Somewhere On The Beach: 2 Br, 2 Ba Condominium In Key West, Sleeps 6

8.9

$436

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Tropical Garden Oasis - Treetop Cottage

$173

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Duval Penthouse

9.6

$834

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Breezy Bungalow (Townhouse)

9.3

$453

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Fiesta Key Rv Resort Standard Room 2

10.0

$236

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Southernmost Sanctuary Apartment

7.8

$246

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Palm Gardens

7.7

$323

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Old Town Suites

8.9

$161

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Key West Harbour Oceanfront Suites

$490

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Conch Cottages of Villas Key West

9.0

$909

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New Casa Solis With Scenic Views and 30' Dock.

9.7

$257

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Kate's Krawl By Duval

9.0

$373

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Casa Cay West Beautiful Tropical House 3 Bedrooms 2 King Suites Pool

10.0

$453

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Nautical Keys Suite at Top Of Duval

9.7

$267

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Fleming-O Quiet Retreat In The Heart Of Old Town Key West- Low September Rate

9.8

$438

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Key Largo - Kawama Tower - Ocean View

9.8

$230

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'in Good Spirits'~waterfront Condo W/Wrap-Around Balcony & Community Pool!

9.5

$327

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Gated Community On Open Water With Dock, Heated Pool, Kayaks, Bikes

10.0

$466

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Downtown Cottage Just Off Famous Duval Street-No Contact Check-In

9.5

$312

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Waterfront Fun And Funky , Newly Renovated Beautiful Duck Key Condo

9.7

$221

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Historic, Dog-Friendly Cottage In The Heart Of Key West W/ Private Hot Tub

8.2

$426

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Poolside Retreat

7.9

$286

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Passover Cottage

9.6

$715

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Papa's Hideaway

8.2

$304

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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	December

cheapest month to stay

41%

expected price decrease

most expensive time to stay

42%

expected price increase

Price

$224 - $636

Highest day of week	Saturday
Cheapest day of week	Sunday

av. price over the last two weeks

Average price (weeknight)

$365

av. price over the last two weeks

Average price (weekend night)

$415

av. price over the last two weeks

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

7.5

$133

Tropical Garden Oasis - Treetop Cottage

$173

Old Town Suites

8.9

$161

Quiet, Quaint, And Conveniently Located! New Pool!

8.8

$177

Key West Villas

8.9

$167

Tired Of Being Inside! Ask About Our November Specials

8.5

$182

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 $361 per night.