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 Marathon
4.99 out of 5 average rating, 107 reviewsSea Ray Cove , 75’ boat dock, 1 block from beach!
Aug. 24 – 31
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
4.88 out of 5 average rating, 73 reviewsIsland Oasis ~ YOUR Paradise Awaits!
Mar. 22 – 29
Home in Cudjoe Key
4.82 out of 5 average rating, 49 reviewsSpanish Queen @Venture Out
Jan. 7 – 14
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
4.9 out of 5 average rating, 31 reviewsWaterfront Venture Out Home
May 29 – Jun. 5
Home in Cudjoe Key
4.95 out of 5 average rating, 22 reviewsWhite Vacation Home. Free cancellation see details
Nov. 16 – 23
Home in Cudjoe Key
4.92 out of 5 average rating, 12 reviewsWaterfront 35’ Dock,80’ pool,20 min Key West
Dec. 21 – 28
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
Sep. 9 – 16
Condo in Key West
4.86 out of 5 average rating, 129 reviewsA Perfect Getaway
May 26 – Jun. 2
Condo in Marathon
4.87 out of 5 average rating, 192 reviewsSombrero Beach Tropical Getaway
Oct. 28 – Nov. 4
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 Colony Beach
5.0 out of 5 average rating, 27 reviewsSea-Esta Condo beach and pool
Nov. 9 – 16
Condo in Marathon
4.94 out of 5 average rating, 94 reviewsWATER FRONT 1bed/1bath, pool, tiki bar, boat ramp
Oct. 11 – 18
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
$150 CAD before taxes and fees
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