Waterfront holiday rentals in Summerland Key
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Top-rated waterfront rentals in Summerland Key
Guests agree: these waterfront rentals are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for waterfront rentals in Summerland Key
Waterfront apartment rentals
Flat in Tavernier
4.95 out of 5 average rating, 147 reviewsBoho FL Keys Condo
12–19 Oct
Flat in Key Largo
4.92 out of 5 average rating, 106 reviews2/1 Oceanfront Apartment with Dockage
15–22 Nov
Flat in Key West
4.89 out of 5 average rating, 135 reviewsKey West Beachside 1400sf, 2 Bedroom Condo
7–14 Mar
Flat in Key West
4.92 out of 5 average rating, 175 reviewsKW Luxury 2/2 Beachfront resort Tropical Oasis
31 Jan – 7 Feb
Flat in Tavernier
4.83 out of 5 average rating, 255 reviewsBreathtaking Oceanfront Views at Tropical Daze
25 Dec – 1 Jan
Flat in Marathon
5.0 out of 5 average rating, 8 reviewsGated Oceanfront Heated Pool
21–28 Jul
Flat in Key West
4.94 out of 5 average rating, 16 reviewsOceanfront Condo in Key West
28 Aug – 4 Sep
Flat in Key Colony Beach
4.86 out of 5 average rating, 77 reviewsBeachside Unit 22 - Private Beach on Atlantic
31 Aug – 7 Sep
Waterfront house rentals
Home in Marathon
4.9 out of 5 average rating, 136 reviewsWaterfront Cozy Modern Retreat w/Deep Canal
5–12 Apr
Home in Cudjoe Key
4.94 out of 5 average rating, 17 reviewsMay Extravaganza - Relax in Paradise!
1–8 Oct
Home in Summerland Key
4.83 out of 5 average rating, 6 reviewsBungalows at Sugarloaf Beach - Little Hammock
30 Mar – 6 Apr
Home in Cudjoe Key
5.0 out of 5 average rating, 23 reviewsParadise in Cudjoe! Perfect Family Home!
4–11 Oct
Home in Cudjoe Key
4.86 out of 5 average rating, 42 reviews*Emerald Seas*-Florida Keys Ocean Front Paradise!
23 Feb – 2 Mar
Home in Cudjoe Key
5.0 out of 5 average rating, 7 reviewsVenture Out- Million Dollar Island Resort
30 Nov – 7 Dec
Home in Cudjoe Key
4.95 out of 5 average rating, 19 reviewsConch Cabana in Paradise 23 miles outside Key West
13–20 Nov
Home in Big Pine Key
4.82 out of 5 average rating, 62 reviewsKey home with open water access!!
2–9 Oct
Waterfront apartment rentals
Apartment in Key West
4.88 out of 5 average rating, 147 reviewsLarge waterfront 2/2 end unit with boat slip
23–30 Aug
Apartment in Tavernier
4.95 out of 5 average rating, 108 reviewsKey Largo Coastal Condo-Ocean View ~ Pool ~ Beach
29 Aug – 5 Sep
Apartment in Tavernier
4.96 out of 5 average rating, 159 reviewsBest View Ocean Pointe Pool Beach King Bed, Gated
29 Sep – 6 Oct
Apartment in Tavernier
4.98 out of 5 average rating, 142 reviewsOcean Views at Ocean Pointe
19–26 Jul
Apartment in Key West
4.85 out of 5 average rating, 143 reviewsAnchor Drop modern elegance upgrades throughout vi
15–22 Sep
Apartment in Tavernier
4.93 out of 5 average rating, 133 reviewsIt's Tiki Time! Top Floor SeaView Mid-Mod 1 Br/1Ba
13–20 Dec
Apartment in Key West
4.83 out of 5 average rating, 243 reviewsLa Dolce Vita, Old Town Steps to Duval! 3 blks bch
6–13 Feb
Apartment in Tavernier
4.91 out of 5 average rating, 110 reviews500 Burton Drive Tavernier, Key Largo
6–13 Dec
Quick stats about waterfront rentals in Summerland Key
Total rentals
120 properties
Rentals with a pool
80 properties have a pool
Pet-friendly rentals
50 properties allow pets
Family-friendly rentals
100 properties are a good fit for families
Total number of reviews
2.2K reviews
Nightly prices starting at
€ 103 before taxes and fees
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