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Search results; Over 1,000 homes in Summerland Key

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Guest favourite
Apartment in Summerland Key
Family Suite at Sugarloaf Key Hotel (Pet Friendly)
1 bedroom, 4 beds, 1 private bathroom
1–6 Oct
,
4.97 out of 5 average rating, 37 reviews
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Superhost
Tiny home in Summerland Key
Cottage
2 bedrooms, 2 beds, 1 bathroom
1–6 Oct
4.94 out of 5 average rating, 82 reviews
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Guest favourite
Home in Summerland Key
Anchor House
4 bedrooms, 7 beds, 2 bathrooms
1–6 Oct
4.95 out of 5 average rating, 116 reviews
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Superhost
Tiny home in Summerland Key
Bungalow
1 bedroom, 2 beds, 1 bathroom
1–6 Oct
4.82 out of 5 average rating, 95 reviews
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Featured hotel
Hotel in Summerland Key
Parmer's Resort, King room
1 bedroom, 1 king bed, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 10 reviews
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Guest favourite
Home in Summerland Key
Captain House
3 bedrooms, 6 beds, 2 bathrooms
1–6 Oct
4.96 out of 5 average rating, 55 reviews
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Guest favourite
Home in Summerland Key
Starlight Serenity - Hideaway with Stunning Views
1 bedroom, 3 beds, 1 bathroom
13–18 Oct
4.95 out of 5 average rating, 40 reviews
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Guest favourite
Home in Summerland Key
Waterfront Oceanside 200' Seawall 3/2 Sleeps 6
3 bedrooms, 3 beds, 2 bathrooms
8–13 Aug
5.0 out of 5 average rating, 8 reviews
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Guest favourite
Cottage in Cudjoe Key
FL Keys Retreat - Community pool and hot tub
2 bedrooms, 4 beds, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 10 reviews
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Guest favourite
Home in Summerland Key
4BR Villa | Private Pool & Tiki | 30 Min to KW
4 bedrooms, 9 beds, 4 bathrooms
19–24 Oct
4.95 out of 5 average rating, 39 reviews
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Guest favourite
Home in Summerland Key
Barry Beach
4 bedrooms, 5 beds, 3 bathrooms
13–18 Oct
5.0 out of 5 average rating, 17 reviews
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Superhost
Home in Marathon
NEW! Reel Escape - 4br/No Stairs/Dock/Kayaks/Bikes
4 bedrooms, 7 beds, 3 bathrooms
17–24 Oct
New place to stay
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Home in Big Pine Key
Your Perfect Florida Keys Escape
3 bedrooms, 3 beds, 2 bathrooms
9–14 Nov
New place to stay
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Guest favourite
Villa in Summerland Key
6BR Villa + Bungalow | Pool & Tiki | 30 Min to KW
6 bedrooms, 7 beds, 6 bathrooms
19–24 Oct
5.0 out of 5 average rating, 13 reviews
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Guest favourite
Home in Cudjoe Key
Palm Breezes! Room for Everyone on the Ocean.
5 bedrooms, 6 beds, 3 bathrooms
2–7 Nov
4.83 out of 5 average rating, 112 reviews
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Guest favourite
Home in Cudjoe Key
Oceanfront 2BR in Venture Out - 35’ Dock + Pool
2 bedrooms, 3 beds, 2 bathrooms
1–6 Oct
4.94 out of 5 average rating, 18 reviews
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Guest favourite
Tiny home in Summerland Key
Waterview Bungalow
1 bedroom, 1 king bed, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 19 reviews
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Guest favourite
Home in Cudjoe Key
Cudjoe Key Home with a View
2 bedrooms, 3 beds, 2 bathrooms
28 Nov – 3 Dec
4.96 out of 5 average rating, 213 reviews
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Top guest favourite
Home in Cudjoe Key
Waterfront, Dock, Pool, Pickleball, near Key West!
2 bedrooms, 3 beds, 1 bathroom
10–15 Oct
4.99 out of 5 average rating, 75 reviews