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Search results; Over 1,000 homes in Summerland Key

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Superhost
Home in Sugarloaf Key
The Guest House - Sugarloaf Beach Key West
2 bedrooms, 7 beds, 2.5 private bathrooms
2–7 Oct
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4.82 out of 5 average rating, 133 reviews
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Featured hotel
Hotel in Summerland Key
Parmer's Resort, King room
1 bedroom, 1 king bed
1–6 Oct
5.0 out of 5 average rating, 10 reviews
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Superhost
Tiny home in Summerland Key
Cottage
2 bedrooms, 2 beds
1–6 Oct
4.94 out of 5 average rating, 82 reviews
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Superhost
Tiny home in Summerland Key
Bungalow
1 bedroom, 2 beds
1–6 Oct
4.82 out of 5 average rating, 95 reviews
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Guest favourite
Home in Summerland Key
Haven House
3 bedrooms, 6 beds
12–17 Oct
4.93 out of 5 average rating, 127 reviews
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Guest favourite
Apartment in Summerland Key
Family Suite at Sugarloaf Key Hotel (Pet Friendly)
1 bedroom, 4 beds
1–6 Oct
4.97 out of 5 average rating, 37 reviews
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Guest favourite
Home in Summerland Key
Starlight Serenity - Hideaway with Stunning Views
1 bedroom, 3 beds
13–18 Oct
4.95 out of 5 average rating, 40 reviews
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Guest favourite
Home in Summerland Key
Barry Beach
4 bedrooms, 5 beds
13–18 Oct
5.0 out of 5 average rating, 17 reviews
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Guest favourite
Home in Summerland Key
Waterfront Oceanside 200' Seawall 3/2 Sleeps 6
3 bedrooms, 3 beds
8–13 Aug
5.0 out of 5 average rating, 8 reviews
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Guest favourite
Tiny home in Summerland Key
Waterview Bungalow
1 bedroom, 1 king bed
1–6 Oct
5.0 out of 5 average rating, 19 reviews
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Featured hotel
Hotel in Marathon
Tranquility Bay Beachfront Hotel and Resort, Trop.
1 bedroom, 1 king bed
17–22 Oct
New place to stay
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Top guest favourite
Home in Cudjoe Key
Oceanfront Cottage with Open Water Views
2 bedrooms, 2 beds
7–12 Oct
5.0 out of 5 average rating, 51 reviews
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Top guest favourite
Room in Big Pine Key
Old Island Life
1 queen bed
1–6 Oct
4.9 out of 5 average rating, 621 reviews
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Guest favourite
Home in Cudjoe Key
Palm Breezes! Room for Everyone on the Ocean.
5 bedrooms, 6 beds
2–7 Nov
4.83 out of 5 average rating, 112 reviews
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Luxe
Home in Summerland Key
4BR Gulf-front house with pool & beach access
4 bedrooms, 4 beds
1–6 Oct
4.56 out of 5 average rating, 25 reviews
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Guest favourite
Villa in Summerland Key
6BR Villa + Bungalow | Pool & Tiki | 30 Min to KW
6 bedrooms, 7 beds
19–24 Oct
5.0 out of 5 average rating, 13 reviews
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Guest favourite
Home in Summerland Key
4BR Villa | Private Pool & Tiki | 30 Min to KW
4 bedrooms, 9 beds
19–24 Oct
4.95 out of 5 average rating, 39 reviews
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Top guest favourite
Home in Cudjoe Key
Rise And Shine On The Water
2 bedrooms, 3 beds
1–6 Oct
4.91 out of 5 average rating, 75 reviews
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Guest favourite
Home in Cudjoe Key
Oceanfront 2BR in Venture Out - 35’ Dock + Pool
2 bedrooms, 3 beds
1–6 Oct
4.94 out of 5 average rating, 18 reviews