filters

Search results; Over 1,000 homes in Upper Sugarloaf Key

Photo 1 of 6
Superhost
Home in Upper Sugarloaf Key
The Lighthouse - Beach Houses Key West
2 bedrooms, 3 beds, 1 private bathroom
26 Sept – 1 Oct
,
4.92 out of 5 average rating, 133 reviews
Photo 1 of 6
Superhost
Tiny home in Summerland Key
Cottage
2 bedrooms, 2 beds, 1 bathroom
6–11 Sept
4.94 out of 5 average rating, 80 reviews
Photo 1 of 6
Superhost
Tiny home in Summerland Key
Bungalow
1 bedroom, 2 beds, 1 bathroom
6–11 Sept
4.81 out of 5 average rating, 89 reviews
Photo 1 of 6
Guest favourite
Apartment in Summerland Key
Family Suite at Sugarloaf Key Hotel (Pet Friendly)
1 bedroom, 4 beds, 1 bathroom
1–6 Sept
4.97 out of 5 average rating, 36 reviews
Photo 1 of 6
Home in Summerland Key
4BR Gulf-front house with pool & beach access
4 bedrooms, 4 beds, 4.5 bathrooms
7–12 Sept
4.56 out of 5 average rating, 25 reviews
Photo 1 of 6
Superhost
Home in Cudjoe Key
Cudjoe Key Home with a View
2 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
4.96 out of 5 average rating, 208 reviews
Photo 1 of 6
Guest favourite
Tiny home in Summerland Key
Waterview Bungalow
1 bedroom, 1 king bed, 1 bathroom
5–10 Sept
5.0 out of 5 average rating, 19 reviews
Photo 1 of 6
Top guest favourite
Home in Cudjoe Key
Oceanfront Cottage with Open Water Views
2 bedrooms, 2 beds, 2 bathrooms
1–6 Sept
5.0 out of 5 average rating, 47 reviews
Photo 1 of 6
Top guest favourite
Home in Summerland Key
Starlight Serenity - Hideaway with Stunning Views
1 bedroom, 3 beds, 1 bathroom
30 Sept – 5 Oct
4.94 out of 5 average rating, 36 reviews
Photo 1 of 6
Guest favourite
Home in Cudjoe Key
Yellow Home - Receive $400 towards a Boat Rental!
3 bedrooms, 3 beds, 2 bathrooms
13–18 Sept
4.88 out of 5 average rating, 42 reviews
Photo 1 of 6
Guest favourite
Cottage in Cudjoe Key
FL Keys Retreat - Community pool and hot tub
2 bedrooms, 4 beds, 1 bathroom
7–12 Sept
5.0 out of 5 average rating, 8 reviews
Photo 1 of 6
Top guest favourite
Home in Cudjoe Key
Jan. Disc, Waterfront Retreat/Dock/Pool/golf cart,
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.97 out of 5 average rating, 29 reviews
Photo 1 of 6
Superhost
Villa in Summerland Key
6BR Villa + Bungalow | Pool & Tiki | 30 Min to KW
6 bedrooms, 7 beds, 6 bathrooms
7–12 Sept
5.0 out of 5 average rating, 12 reviews
Photo 1 of 6
Guest favourite
Home in Summerland Key
9BR Estate | 3 Homes/2 Pools/Hot tub -30 Min to KW
9 bedrooms, 16 beds, 9 bathrooms
7–12 Sept
5.0 out of 5 average rating, 18 reviews
Photo 1 of 6
Top guest favourite
Home in Cudjoe Key
Tiki Time in Cudjoe Key 136
2 bedrooms, 2 beds, 2 bathrooms
13–18 Sept
4.96 out of 5 average rating, 56 reviews
Photo 1 of 6
Guest favourite
Home in Cudjoe Key
Oceanside home 107,dock,kayaks,bikes,pool,fishing,
2 bedrooms, 3 beds, 3 bathrooms
7–12 Sept
4.94 out of 5 average rating, 34 reviews
Photo 1 of 6
Top guest favourite
Home in Cudjoe Key
Rise And Shine On The Water
2 bedrooms, 3 beds, 2 bathrooms
16–21 Sept
4.91 out of 5 average rating, 75 reviews
Photo 1 of 6
Top guest favourite
Home in Cudjoe Key
Ocean's Edge VO Pad Boards, Kayak, Bikes-30 min KW
2 bedrooms, 4 beds, 1 bathroom
3–8 Oct
4.97 out of 5 average rating, 93 reviews
Photo 1 of 6
Top guest favourite
Boat in Key West
Wake Up On The Water | Luxury Marina | Key West
3 bedrooms, 3 double beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 12 reviews