House vacation rentals in Summerland Key
Find and book unique houses on Airbnb
Top-rated house rentals in Summerland Key
Guests agree: these houses 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 house rentals
House rentals with a pool
Home in Cudjoe Key
5.0 out of 5 average rating, 7 reviewsVenture Out- Million Dollar Island Resort
Dec 7 – 14
Home in Cudjoe Key
4.86 out of 5 average rating, 43 reviews*Emerald Seas*-Florida Keys Ocean Front Paradise!
Nov 1 – 8
Home in Cudjoe Key
4.82 out of 5 average rating, 49 reviewsSpanish Queen @Venture Out
Mar 23 – 30
Home in Cudjoe Key
4.95 out of 5 average rating, 19 reviewsConch Cabana in Paradise 23 miles outside Key West
Aug 19 – 26
Home in Cudjoe Key
4.82 out of 5 average rating, 11 reviewsRise-N-Shine
Dec 12 – 19
Home in Cudjoe Key
4.88 out of 5 average rating, 73 reviewsIsland Oasis ~ YOUR Paradise Awaits!
Mar 13 – 20
Home in Cudjoe Key
4.86 out of 5 average rating, 28 reviewsKeys Island Villa - Venture Out Home 354
Oct 3 – 10
Home in Cudjoe Key
5.0 out of 5 average rating, 12 reviewsSea Turtle Cove
Oct 12 – 19
Weekly house rentals
Home in Cudjoe Key
5.0 out of 5 average rating, 23 reviewsParadise in Cudjoe! Perfect Family Home!
Oct 4 – 11
Home in Marathon
4.97 out of 5 average rating, 34 reviewsThe Gulf Cottage at Marathon Key
Jun 28 – Jul 5
Home in Marathon
4.94 out of 5 average rating, 35 reviewsGorgeous Ocean View Home!
Mar 16 – 23
Home in Marathon
5.0 out of 5 average rating, 10 reviewsCanal Front, Boat Dock, Updated!
Aug 9 – 16
Home in Cudjoe Key
4.92 out of 5 average rating, 12 reviewsWaterfront 35’ Dock,80’ pool,20 min Key West
Dec 21 – 28
Home in Cudjoe Key
4.9 out of 5 average rating, 31 reviewsWaterfront Venture Out Home
May 29 – Jun 5
Home in Cudjoe Key
5.0 out of 5 average rating, 3 reviewsLatitudes-Ocean Front Pool
Nov 9 – 16
Home in Marathon
4.96 out of 5 average rating, 84 reviewsAngler’s Eden
Nov 12 – 19
Private house rentals
Home in Marathon
4.98 out of 5 average rating, 84 reviewsAnglers Terrace, Condé Nast Traveler's Best Airbnb
Aug 3 – 10
Home in Duck Key
5.0 out of 5 average rating, 31 reviewsPrivate Pool Tropical Oasis - Centrally Located
Nov 20 – 27
Home in Cudjoe Key
4.88 out of 5 average rating, 17 reviewsPelican's Roost, Waterfront comfort at Venture Out
Apr 16 – 23
Home in Marathon
4.97 out of 5 average rating, 59 reviewsPrivate 174ft Dock, Boat Launch, Sombrero Beach
Jun 17 – 24
Home in Key Largo
5.0 out of 5 average rating, 14 reviewsPrivate 1 Acre House~Private Beach~Tiki Hut~Dock
Dec 14 – 21
Home in Cudjoe Key
4.85 out of 5 average rating, 26 reviewsLower Keys Paradise
Apr 11 – 18
Home in Cudjoe Key
4.78 out of 5 average rating, 9 reviewsCuddie Cottage: Open Water Views, Pool/Hot Tub!
Jul 3 – 10
Home in Key Colony Beach
5.0 out of 5 average rating, 96 reviewsABeachBungalow-60’dock w/ access to pool and beach
Apr 19 – 26
Quick stats about house rentals in Summerland Key
Total rentals
170 properties
Rentals with a pool
100 properties have a pool
Pet-friendly rentals
60 properties allow pets
Family-friendly rentals
150 properties are a good fit for families
Total number of reviews
2.5K reviews
Nightly prices starting at
R2,413 ZAR before taxes and fees
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