Key West Vacation Rentals

Come make memories in the Florida Keys and escape to your very own tropical island paradise. We have made-to-order Key West Hotels, Key West Condominiums, Islamorada Vacation Homes, and Key Largo Resorts right at your fingertips. Take a look around, check out the amenities, and find the perfect accommodation to make your next vacation one to remember.

To see photos, amenities and other details on all Key West vacation rentals, choose from our list below. Or use our custom search feature to find the Key West vacation rental that's best for you.

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Louisa's Garden

1 BD

1 BA

Sleeps 2

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Dancing Palms

2 BD

2 BA

Sleeps 4

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Shipyard Perch

2 BD

2 BA

Sleeps 4

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

The Southernmost Comfort House

4 BD

3.5 BA

Sleeps 10

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Casa Cubana At Duval Square R14

2 BD

2.5 BA

Sleeps 3

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Julia Whitehead Guest Suites

3 BD

3.5 BA

Sleeps 6

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Atlantic Parrot

2 BD

2 BA

Sleeps 6

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Leeward Isle

2 BD

1 BA

Sleeps 6

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Egret House

2 BD

1.5 BA

Sleeps 6

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Duval Square Penthouse R19

2 BD

2.5 BA

Sleeps 6

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Bottoms Up

1 BD

1 BA

Sleeps 2

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Truman's Garden

2 BD

2.5 BA

Sleeps 2

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Bahama House

3 BD

3 BA

Sleeps 8

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Island Hideaway

2 BD

2.5 BA

Sleeps 4

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Cool Breeze

2 BD

2.5 BA

Sleeps 6

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Seaport Retreat

3 BD

2.5 BA

Sleeps 6

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

The Frontier Suite

2 BD

2 BA

Sleeps 6

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Atlantic Ocean View

2 BD

2 BA

Sleeps 6

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Mermaid's Retreat

1 BD

1.5 BA

Sleeps 2

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Sunshine Drive

3 BD

3 BA

Sleeps 10

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Grinnell Street Getaway

1 BD

1 BA

Sleeps 2

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Tropical Escape

3 BD

3 BA

Sleeps 6

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Key Lime Calypso

2 BD

1 BA

Sleeps 6

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Cabana Retreat

3 BD

3 BA

Sleeps 6

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Windward Isle

2 BD

1 BA

Sleeps 6

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Conch Casa

2 BD

1 BA

Sleeps 6

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Sunshine Stunner & Casita

5 BD

5 BA

Sleeps 12

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Putting In Paradise

2 BD

1.5 BA

Sleeps 4

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Casa Hueso

4 BD

3.5 BA

Sleeps 8

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Hemingway Hideaway

3 BD

3 BA

Sleeps 6

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Truman @ Duval - Unit B

1 BD

2 BA

Sleeps 4

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Secret Garden

2 BD

1 BA

Sleeps 4

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Hemingway's View

3 BD

2 BA

Sleeps 8

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

The Tipsy Mermaid

3 BD

2.5 BA

Sleeps 6

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Saddlebunch Siesta

3 BD

3 BA

Sleeps 8

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Key West Holidays

4 BD

3 BA

Sleeps 10

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Salty Air Retreat

2 BD

1 BA

Sleeps 4

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Conch Cottage

1 BD

1 BA

Sleeps 2

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Paradise Suite

1 BD

1.5 BA

Sleeps 2

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Point Break

4 BD

4 BA

Sleeps 12

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Point Break Suite B

3 BD

2 BA

Sleeps 8

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Tradewinds At Smathers Beach

3 BD

2 BA

Sleeps 8

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

The Headquarters

2 BD

1 BA

Sleeps 4

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Salty Sunrise #311

2 BD

2 BA

Sleeps 6

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Sunrise Suites - Butterfly Nest 107

2 BD

2 BA

Sleeps 2

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Truman @ Duval - Unit D

2 BD

1 BA

Sleeps 4

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Sapphire Sabbatical

3 BD

2 BA

Sleeps 6

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Coconut Cottage

4 BD

4.5 BA

Sleeps 14

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Olivia Street Retreat

1 BD

1 BA

Sleeps 4

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Flagler's Crossing

2 BD

2.5 BA

Sleeps 4

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Bay Harbor View

5 BD

3 BA

Sleeps 18

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Keys Please

3 BD

2.5 BA

Sleeps 6

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Tarpon Watch

2 BD

2 BA

Sleeps 6

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Casa Bonita At Duval Square R1

2 BD

2.5 BA

Sleeps 6

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

The North Star

2 BD

2 BA

Sleeps 4

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Borrowed Time

1 BD

1 BA

Sleeps 2

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Tropical Retreat

3 BD

2.5 BA

Sleeps 6

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Passover Cottage

2 BD

2 BA

Sleeps 4

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Last Minute

3 BD

2 BA

Sleeps 6

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Casa Caribe At Duval Square, Unit R9

2 BD

2.5 BA

Sleeps 6

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Truman @ Duval - Studio A

1 BD

1 BA

Sleeps 2

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Porter Paradise

2 BD

2.5 BA

Sleeps 2

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Duval Street Retreat

2 BD

1 BA

Sleeps 6

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Amelia House

3 BD

2 BA

Sleeps 8

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Petronia Paradise

2 BD

2 BA

Sleeps 4

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Coral Queen Palm

3 BD

2 BA

Sleeps 6

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Flagler Station

3 BD

2 BA

Sleeps 6

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Sunshine Casita

1 BD

1 BA

Sleeps 2

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Admirals Gold

4 BD

3.5 BA

Sleeps 8

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Casa Atlantic

3 BD

3 BA

Sleeps 9

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Seafoam Escape

2 BD

2 BA

Sleeps 4

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Oceana Suite

1 BD

1 BA

Sleeps 2

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Margaret Street Retreat

2 BD

2 BA

Sleeps 6

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Tradewinds

4 BD

2 BA

Sleeps 12

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Sunset Bay

4 BD

3.5 BA

Sleeps 16

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Casa De Sunshine

2 BD

3 BA

Sleeps 2

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Island Retreat

2 BD

2.5 BA

Sleeps 6

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Tropical Vibes

4 BD

5 BA

Sleeps 8

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Seashore At The Shipyard

2 BD

1 BA

Sleeps 4

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Jewel On Jade

2 BD

2 BA

Sleeps 6

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Gingerbread

1 BD

1 BA

Sleeps 2

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Truman @ Duval - Unit C

1 BD

1 BA

Sleeps 2

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

The Frontier Flat

1 BD

1 BA

Sleeps 4

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Seagrass Suite

1 BD

1 BA

Sleeps 2

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

The Coral Cove

1 BD

1 BA

Sleeps 2

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Sunset At Harbour Place

2 BD

2 BA

Sleeps 6

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Baya House

2 BD

2 BA

Sleeps 4

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Southernmost Retreat

4 BD

2 BA

Sleeps 10

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Duval Hideaway

2 BD

1 BA

Sleeps 4

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Shipyard Seaclusion

2 BD

1 BA

Sleeps 4

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Casa Havana At Duval Square R22

2 BD

2.5 BA

Sleeps 6

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Mangrove Lagoon

2 BD

2.5 BA

Sleeps 4

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Cool Breeze

2 BD

2.5 BA

Sleeps 6

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Coconut Cottage

1 BD

1 BA

Sleeps 4

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool

Sunset Bay

4 BD

3 BA

Sleeps 11

Pet Friendly

Washer/Dryer

King bed(s)

Deck/Patio

Courtyard

Non-Metered Parking

Private Parking

Private Pool