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Search results; Over 1,000 homes in Summerland Key

Home in Summerland Key
OCEAN FRONT PARADISE/ PRIVATE DOCK/AWESOME VIEWS
3 bedrooms, 6 beds, 2 private bathrooms
1–6 Aug
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4.58 out of 5 average rating, 102 reviews
Guest favourite
Home in Summerland Key
Waterfront Anchor House with Boat Basin & Ramp!
4.95 out of 5 average rating, 114 reviews, 4 bedrooms, 6 beds, 2 bathrooms
8–13 Aug
Superhost
Tiny home in Summerland Key
Cottage
4.92 out of 5 average rating, 65 reviews, 2 bedrooms, 2 beds, 1 bathroom
26–31 Jul
Guest favourite
Apartment in Summerland Key
Family Suite at Sugarloaf Key Hotel (Pet Friendly)
4.97 out of 5 average rating, 33 reviews, 1 bedroom, 4 beds, 1 bathroom
14–19 Jul
Guest favourite
Home in Summerland Key
Waterfront Captain House with Boat Basin & Ramp!
4.96 out of 5 average rating, 52 reviews, 3 bedrooms, 6 beds, 2 bathrooms
8–13 Aug
Guest favourite
Home in Summerland Key
Waterfront Beach House with Dock & Heated Pool!
5.0 out of 5 average rating, 12 reviews, 4 bedrooms, 5 beds, 3 bathrooms
20–25 Sept
Guest favourite
Cottage in Cudjoe Key
FL Keys Retreat - Community pool and hot tub
5.0 out of 5 average rating, 5 reviews, 2 bedrooms, 4 beds, 1 bathroom
15–20 Aug
Guest favourite
Home in Cudjoe Key
Cudjoe Key Home with a View
4.97 out of 5 average rating, 201 reviews, 2 bedrooms, 3 beds, 2 bathrooms
22–27 Aug
Top guest favourite
Home in Summerland Key
Starlight Serenity - Hideaway with Stunning Views
4.97 out of 5 average rating, 30 reviews, 1 bedroom, 3 beds, 1 bathroom
24–29 Jul
Guest favourite
Home in Cudjoe Key
New Construction. $299 per night.
5.0 out of 5 average rating, 17 reviews, 2 bedrooms, 2 bathrooms
15–20 Jul
Superhost
Tiny home in Summerland Key
Bungalow
4.79 out of 5 average rating, 76 reviews, 1 bedroom, 2 beds, 1 bathroom
3–8 Aug
Guest favourite
Villa in Summerland Key
6BR Villa + Bungalow | Pool & Tiki | 30 Min to KW
5.0 out of 5 average rating, 8 reviews, 6 bedrooms, 10 beds, 6 bathrooms
7–12 Sept
Home in Cudjoe Key
Ocean Breeze Retreat w/ Dock| Keys Escape
5.0 out of 5 average rating, 3 reviews, 2 bedrooms, 4 beds, 2 bathrooms
24–29 Aug
Top guest favourite
Guest suite in Big Pine Key
Old Island Life
4.89 out of 5 average rating, 614 reviews, 1 bedroom, 1 bed, 1 bathroom
14–19 Jul
Guest favourite
Cottage in Cudjoe Key
Beautiful Cottage & Amenities in Gated Community
4.97 out of 5 average rating, 123 reviews, 2 bedrooms, 3 beds, 2 bathrooms
24–29 Jul
Superhost
Tiny home in Big Pine Key
Cottage 30 min from Key West, free parking, pool
4.88 out of 5 average rating, 123 reviews, 1 bedroom, 3 beds, 1 bathroom
9–14 Aug
Top guest favourite
Home in Cudjoe Key
Ocean's Edge VO Pad Boards, Kayak, Bikes-30 min KW
4.97 out of 5 average rating, 86 reviews, 2 bedrooms, 4 beds, 1 bathroom
27 Aug – 1 Sept
Guest favourite
Home in Cudjoe Key
Waterfront home in florida keys 35’ dock for boat
5.0 out of 5 average rating, 13 reviews, 1 bedroom, 2 beds, 1 bathroom
14–19 Jul
Holiday home in Cudjoe Key
Crystal Clear Canal Front 2/1 on Cudjoe Key!
4.71 out of 5 average rating, 83 reviews, 2 bedrooms, 3 beds, 1 bathroom
18–23 Jul