Vacation rentals with a pool in Cudjoe Key
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Cudjoe Key
Guests agree: these homes with a pool 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 Cudjoe Key rentals with a pool
House rentals with a pool
Home in Key Colony Beach
4.96 out of 5 average rating, 134 reviewsBeautiful open plan remodeled home in Key Colony
Oct 23 – 30
Home in Cudjoe Key
4.86 out of 5 average rating, 43 reviews*Emerald Seas*-Florida Keys Ocean Front Paradise!
Oct 10 – 17
Home in Cudjoe Key
5.0 out of 5 average rating, 7 reviewsVenture Out- Million Dollar Island Resort
Nov 30 – Dec 7
Home in Cudjoe Key
4.86 out of 5 average rating, 28 reviewsKeys Island Villa - Venture Out Home 354
Sep 30 – Oct 7
Home in Cudjoe Key
4.88 out of 5 average rating, 73 reviewsIsland Oasis ~ YOUR Paradise Awaits!
Sep 9 – 16
Home in Cudjoe Key
4.82 out of 5 average rating, 49 reviewsSpanish Queen @Venture Out
Aug 18 – 25
Home in Cudjoe Key
4.95 out of 5 average rating, 19 reviewsConch Cabana in Paradise 23 miles outside Key West
Apr 15 – 22
Home in Cudjoe Key
4.92 out of 5 average rating, 12 reviewsWaterfront 35’ Dock,80’ pool,20 min Key West
Dec 13 – 20
Condo rentals with a pool
Condo in Key Colony Beach
4.91 out of 5 average rating, 112 reviewsBeachside Unit 39 Tiki Huts, Private Beach & Pool
Aug 22 – 29
Condo in Key West
4.88 out of 5 average rating, 147 reviewsLarge waterfront 2/2 end unit with boat slip
Apr 14 – 21
Condo in Key West
4.86 out of 5 average rating, 129 reviewsA Perfect Getaway
Dec 8 – 15
Condo in Marathon
4.87 out of 5 average rating, 192 reviewsSombrero Beach Tropical Getaway
Oct 17 – 24
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
Feb 16 – 23
Condo in Key Colony Beach
5.0 out of 5 average rating, 27 reviewsSea-Esta Condo beach and pool
Nov 2 – 9
Condo in Marathon
5.0 out of 5 average rating, 6 reviewsOceanside Spacious Studio Escape
Jul 18 – 25
Quick stats about vacation rentals with a pool in Cudjoe Key
Total rentals
140 properties
Rentals with dedicated workspaces
40 properties have a dedicated workspace
Pet-friendly rentals
50 properties allow pets
Family-friendly rentals
110 properties are a good fit for families
Total number of reviews
3.8K reviews
Nightly prices starting at
€ 103 before taxes and fees
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