Waterfront vacation rentals in Summerland Key
Find and book unique waterfront rentals on Airbnb
Top-rated waterfront rentals in Summerland Key
Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Summerland Key waterfront rentals
Waterfront apartment rentals
Apartment in Key West
4.89 out of 5 average rating, 136 reviewsKey West Beachside 1400sf, 2 Bedroom Condo
Oct 6 – 13
Apartment in Key West
4.92 out of 5 average rating, 175 reviewsKW Luxury 2/2 Beachfront resort Tropical Oasis
Mar 10 – 17
Apartment in Marathon
5.0 out of 5 average rating, 8 reviewsGated Oceanfront Heated Pool
Nov 11 – 18
Apartment in Key West
4.94 out of 5 average rating, 16 reviewsOceanfront Condo in Key West
Sep 30 – Oct 7
Apartment in Marathon
5.0 out of 5 average rating, 5 reviewsMarathon Studio on Lovely Resort w/Amenities
Dec 25 – Jan 1
Apartment in Key Colony Beach
4.83 out of 5 average rating, 78 reviewsBeachside Unit 22 - Private Beach on Atlantic
Dec 16 – 23
Apartment in Key West
5.0 out of 5 average rating, 3 reviewsPartial ocean view studio with king bed
Apr 12 – 19
Apartment in Marathon
4.95 out of 5 average rating, 38 reviewsDock POOL Kayaks Bikes Beach2mi WalkToStores
Mar 7 – 14
Waterfront house rentals
Home in Cudjoe Key
4.94 out of 5 average rating, 17 reviewsMay Extravaganza - Relax in Paradise!
Oct 1 – 8
Home in Summerland Key
4.86 out of 5 average rating, 7 reviewsBungalows at Sugarloaf Beach - Little Hammock
Feb 23 – Mar 2
Home in Cudjoe Key
5.0 out of 5 average rating, 23 reviewsParadise in Cudjoe! Perfect Family Home!
Oct 4 – 11
Home in Cudjoe Key
4.86 out of 5 average rating, 43 reviews*Emerald Seas*-Florida Keys Ocean Front Paradise!
Sep 12 – 19
Home in Cudjoe Key
4.82 out of 5 average rating, 49 reviewsSpanish Queen @Venture Out
Jan 7 – 14
Home in Cudjoe Key
4.86 out of 5 average rating, 28 reviewsKeys Island Villa - Venture Out Home 354
Sep 26 – Oct 3
Home in Cudjoe Key
4.95 out of 5 average rating, 19 reviewsConch Cabana in Paradise 23 miles outside Key West
Apr 8 – 15
Home in Cudjoe Key
4.82 out of 5 average rating, 11 reviewsRise-N-Shine
Mar 23 – 30
Waterfront condo rentals
Condo in Key West
4.88 out of 5 average rating, 147 reviewsLarge waterfront 2/2 end unit with boat slip
Sep 9 – 16
Condo in Key West
4.85 out of 5 average rating, 143 reviewsAnchor Drop modern elegance upgrades throughout vi
Sep 15 – 22
Condo in Key West
4.83 out of 5 average rating, 243 reviewsLa Dolce Vita, Old Town Steps to Duval! 3 blks bch
Oct 28 – Nov 4
Condo in Key West
4.96 out of 5 average rating, 76 reviewsHidden Beach unit 1 The Perfect Place to stay
Dec 2 – 9
Condo in Key Colony Beach
5.0 out of 5 average rating, 27 reviewsSea-Esta Condo beach and pool
Nov 9 – 16
Condo in Marathon
5.0 out of 5 average rating, 7 reviewsOcean Potion NEW 1B/2B 3Balconies Ocean View
Oct 17 – 24
Condo in Key West
5.0 out of 5 average rating, 28 reviewsGorgeous Ocean View in Paradise
Aug 31 – Sep 7
Condo in Key West
4.89 out of 5 average rating, 9 reviewsOcean View Residence
Dec 10 – 17
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
R2,042 ZAR before taxes and fees
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