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Search results; Over 1,000 places in Summerland Key

Guest favourite
Home in Cudjoe Key
May Extravaganza - Relax in Paradise!
Hosted by a business
1–8 Oct
4.94 out of 5 average rating, 17 reviews
Home in Summerland Key
Beach House Key West, with a daily rentals license
Hosted by Roxi
22–27 Apr
4.59 out of 5 average rating, 27 reviews
Home in Big Pine Key
Nature's Paradise-Ingrd Pool-Great Monthly Rental$
Hosted by Brian
15–22 May
Superhost
Home in Summerland Key
Waterfront Captain House with Boat Basin & Ramp!
Hosted by a business
2–7 May
4.88 out of 5 average rating, 16 reviews
Guest favourite
Home in Summerland Key
Waterfront Anchor House with Boat Basin & Ramp!
WaterfrontSea and bay views,
17–22 AugHosted by a business,
4.97 out of 5 average rating, 61 reviews
Home in Summerland Key
OCEAN FRONT PARADISE/ PRIVATE DOCK/AWESOME VIEWS
Hosted by Alex
27 Apr – 2 May
4.52 out of 5 average rating, 65 reviews
Home in Summerland Key
Pelico Palms Sunset Cottage
Hosted by Nate
19–24 Apr
4.91 out of 5 average rating, 23 reviews
Guest favourite
Home in Ramrod Key
Canalfront 3BD/2BA|FLKeys|POOL|DOCK
Hosted by Vacation Rentals
6–11 Mar
5.0 out of 5 average rating, 6 reviews
Home in Summerland Key
Powell Family Resort
Hosted by Pamela
22–27 Apr
4.86 out of 5 average rating, 35 reviews
Home in Summerland Key
Kelly’s Kabin - Private FL Keys Cottage
Hosted by Kristin
12–17 May
4.68 out of 5 average rating, 28 reviews
Home in Summerland Key
Peaceful Paradise- Summerland Cove!
Hosted by Robert
15–20 Mar
New place to stay
Home in Key West
Waterfront Key West House w/Dock
Hosted by Andrew
8–14 May
5.0 out of 5 average rating, 4 reviews
Home in Summerland Key
2 Bedroom Sunset Bungalow
Hosted by Little Torch Cottages
19–24 Apr
4.7 out of 5 average rating, 90 reviews
Superhost
Home in Cudjoe Key
*Emerald Seas*-Florida Keys Ocean Front Paradise!
Hosted by Shawn
28 Apr – 3 May
4.86 out of 5 average rating, 42 reviews
Guest favourite
Cottage in Little Torch Key
Waterfront Cozy Cottage with Boat Ramp & Dock!
Hosted by a business
26–31 May
4.91 out of 5 average rating, 145 reviews
Superhost
Home in Summerland Key
Family Retreat
Hosted by a business
4–11 May
Home in Summerland Key
4BR Gulf-front house with pool & beach access
Hosted by a business
29 Apr – 4 May
4.45 out of 5 average rating, 11 reviews
Home in Summerland Key
Pelico Palm Villa
Hosted by Nate
22–27 Apr
5.0 out of 5 average rating, 9 reviews