filters

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

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, 132 reviews
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
Superhost
Tiny home in Summerland Key
Bungalow
1 bedroom, 2 beds, 1 bathroom
6–11 Sept
4.8 out of 5 average rating, 87 reviews
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
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, 18 reviews
Top guest favourite
Home in Summerland Key
Starlight Serenity - Hideaway with Stunning Views
1 bedroom, 3 beds, 1 bathroom
11–16 Sept
4.97 out of 5 average rating, 35 reviews
Home in Summerland Key
4BR Gulf-front house with pool & beach access
4 bedrooms, 4 beds, 4.5 bathrooms
1–6 Sept
4.56 out of 5 average rating, 25 reviews
Superhost
Apartment in Summerland Key
Standard Suite at Sugarloaf Key Hotel
1 bedroom, 2 beds, 1 bathroom
1–6 Sept
5.0 out of 5 average rating, 5 reviews
Guest favourite
Boat in Key West
Stay on Roxie - free transport & snacks, BYOB.
1 bedroom, 2 beds, 1 bathroom
6–11 Sept
4.9 out of 5 average rating, 245 reviews
Top guest favourite
Guest suite in Big Pine Key
Old Island Life
1 bedroom, 1 queen bed, 1 bathroom
7–12 Sept
4.89 out of 5 average rating, 619 reviews
Guest favourite
Home in Cudjoe Key
Cudjoe Key Home with a View
2 bedrooms, 3 beds, 2 bathrooms
24–29 Sept
4.96 out of 5 average rating, 208 reviews
Boat in Key West
Serenova - 58' Leopard Catamaran
3 bedrooms, 3 queen beds, 2 bathrooms
7–12 Sept
New place to stay
Superhost
Cottage in Little Torch Key
Waterfront Cozy Cottage with Boat Ramp & Dock!
2 bedrooms, 4 beds, 1 bathroom
1–6 Sept
4.89 out of 5 average rating, 184 reviews
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
Home in Big Pine Key
Your Perfect Florida Keys Escape
3 bedrooms, 3 beds, 2 bathrooms
1–6 Sept
New place to stay
Home in Cudjoe Key
Heron House at Venture Out Resort
2 bedrooms, 5 beds, 2 bathrooms
5–10 Sept
5.0 out of 5 average rating, 5 reviews
Guest favourite
Home in Summerland Key
Waterfront Haven House with Boat Basin & Ramp!
3 bedrooms, 6 beds, 1 bathroom
13–18 Sept
4.93 out of 5 average rating, 127 reviews
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, 46 reviews
Home in Big Pine Key
Falcon’s Cove in Big Pine Key
2 bedrooms, 3 beds, 1.5 bathrooms
9–14 Sept