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
4.97 out of 5 average rating, 118 reviewsMarathon one-level home on the Marina - with slip!
Dec 20 – 27
Home in Cudjoe Key
4.95 out of 5 average rating, 19 reviewsConch Cabana in Paradise 23 miles outside Key West
Jan 13 – 20
Home in Cudjoe Key
4.83 out of 5 average rating, 6 reviewsSailfish Haven
Sep 11 – 18
Home in Cudjoe Key
4.82 out of 5 average rating, 49 reviewsSpanish Queen @Venture Out
Jan 6 – 13
Home in Cudjoe Key
4.87 out of 5 average rating, 45 reviews*Emerald Seas*-Florida Keys Ocean Front Paradise!
Mar 3 – 10
Home in Cudjoe Key
4.86 out of 5 average rating, 28 reviewsKeys Island Villa - Venture Out Home 354
Oct 8 – 15
Home in Cudjoe Key
4.88 out of 5 average rating, 73 reviewsIsland Oasis ~ YOUR Paradise Awaits!
Jan 15 – 22
Home in Cudjoe Key
4.92 out of 5 average rating, 12 reviewsWaterfront 35’ Dock,80’ pool,20 min Key West
Mar 15 – 22
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
Oct 27 – Nov 3
Condo in Key West
4.86 out of 5 average rating, 130 reviewsA Perfect Getaway
Jul 20 – 27
Condo in Key West
4.89 out of 5 average rating, 148 reviewsLarge waterfront 2/2 end unit with boat slip
Mar 22 – 29
Condo in Marathon
4.87 out of 5 average rating, 192 reviewsSombrero Beach Tropical Getaway
Nov 10 – 17
Condo in Key West
4.85 out of 5 average rating, 143 reviewsAnchor Drop modern elegance upgrades throughout vi
Mar 10 – 17
Condo in Key West
4.83 out of 5 average rating, 243 reviewsLa Dolce Vita, Old Town Steps to Duval! 3 blks bch
Apr 24 – May 1
Condo in Key Colony Beach
5.0 out of 5 average rating, 27 reviewsSea-Esta Condo beach and pool
Nov 9 – 16
Condo in Key West
4.99 out of 5 average rating, 80 reviews*Come to my Deck for a time you won't Forget!
Mar 15 – 22
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
$110 before taxes and fees
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