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Search results; Over 1,000 homes in Key West

Boutique hotel in Key West

Cabana Cottage| Complimentary Breakfast&Happy Hour

1 bedroom, 1 bed, 1 private bathroom

5–10 Mar

$6,452 SGD for 5 nights

,

Room in Key West

*Near Smathers Beach | Pool + Dining & Bar

2 queen beds

23–28 Aug

Extended stay discount

Free cancellation

4.82 out of 5 average rating, 22 reviews

Superhost

Home in Marathon

Cielo del Mar - Waterfront - Heated Pool - Dock

4 bedrooms, 9 beds

20–27 Aug

New place to stay

Guest favourite

Houseboat in Key West

Tiki Suites ~ Original Tiki ~ Floating Bungalows

1 bedroom, 1 bed

23–28 Aug

$3,942 SGD for 5 nights

4.91 out of 5 average rating, 558 reviews

Superhost

Home in Marathon

*NEW!*Life is a Marathon~VIEWS!~Pool~Dock~HotTub!

4 bedrooms, 5 beds

26 Sept – 3 Oct

$2,647 SGD for 7 nights

New place to stay

Luxe

Home in Key West

Altair House at Lunara Bay

6 bedrooms, 9 beds

30 Aug – 4 Sept

$7,059 SGD for 5 nights

4.86 out of 5 average rating, 44 reviews

Featured hotel

Room in Key West

High floor island view two queen beds

2 queen beds

20–25 Aug

$1,351 SGD for 5 nights

+$154 SGD Airbnb credit

New place to stay

Luxe

Home in Key West

Floralee House at Lunara Bay

6 bedrooms, 9 beds

30 Aug – 4 Sept

$7,136 SGD for 5 nights

4.95 out of 5 average rating, 39 reviews

Top guest favourite

Boat in Key West

Wake Up On The Water | Luxury Marina | Key West

3 bedrooms, 3 double beds

12–17 Sept

5.0 out of 5 average rating, 10 reviews

Guest favourite

Home in Big Pine Key

Fishermen's Paradise | Pool, 220' Dock & Open-Wate

3 bedrooms, 3 beds

5–10 Oct

$6,661 SGD for 5 nights

4.91 out of 5 average rating, 102 reviews

Superhost

Home in Key West

Casa Loca! By Rent Key West Vacations 1/2 block

3 bedrooms, 4 beds

20–25 Aug

4.9 out of 5 average rating, 91 reviews

Superhost

Boat in Key West

Waterfront & Heated Pool - Break Awai Floating Vil

2 bedrooms, 2 queen beds

29 Aug – 3 Sept

$2,945 SGD for 5 nights

5.0 out of 5 average rating, 4 reviews

Luxe

Home in Key West

The Seagate Estate at Lunara Bay

4 bedrooms, 5 beds

20–25 Sept

$6,542 SGD for 5 nights

4.81 out of 5 average rating, 63 reviews

Boat in Key West

Serenova - 58' Leopard Catamaran

3 bedrooms, 3 queen beds

28 Aug – 2 Sept

New place to stay

Home in Summerland Key

4BR Gulf-front house with pool & beach access

4 bedrooms, 4 beds

20–25 Aug

$13,031 SGD for 5 nights

4.56 out of 5 average rating, 25 reviews

Featured hotel

Room in Key West

Classic Double Queen City/Balcony

2 queen beds

23–28 Aug

$989 SGD for 5 nights

+$83 SGD Airbnb credit

4.8 out of 5 average rating, 61 reviews

Guest favourite

Home in Key West

Waterfront Home in Key Cove Landings

4 bedrooms, 6 beds

21–26 Aug

$6,005 SGD for 5 nights

5.0 out of 5 average rating, 24 reviews

Top guest favourite

Home in Marathon

Waterfront 6BR Luxury Retreat w/ Pool & Dock

6 bedrooms, 10 beds

3–10 Oct

$7,553 SGD for 7 nights

5.0 out of 5 average rating, 31 reviews

Guest favourite

Home in Cudjoe Key

Palm Breezes! Room for Everyone on the Ocean.

5 bedrooms, 6 beds

8–13 Jan

4.83 out of 5 average rating, 111 reviews