Holiday 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.
Holiday rentals for every style
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Popular amenities for Cudjoe Key rentals with a pool
House rentals with a pool
Home in Marathon
4.97 out of 5 average rating, 117 reviewsMarathon one-level home on the Marina - with slip!
22–29 May
Home in Cudjoe Key
4.86 out of 5 average rating, 42 reviews*Emerald Seas*-Florida Keys Ocean Front Paradise!
23 Feb – 2 Mar
Home in Cudjoe Key
4.86 out of 5 average rating, 28 reviewsKeys Island Villa - Venture Out Home 354
30 Sept – 7 Oct
Home in Cudjoe Key
4.88 out of 5 average rating, 72 reviewsIsland Oasis ~ YOUR Paradise Awaits!
9–16 Sept
Home in Cudjoe Key
4.82 out of 5 average rating, 49 reviewsSpanish Queen @Venture Out
26 Nov – 3 Dec
Home in Cudjoe Key
4.91 out of 5 average rating, 11 reviewsWaterfront 35’ Dock,80’ pool,20 min Key West
13–20 Dec
Home in Cudjoe Key
4.82 out of 5 average rating, 11 reviewsRise-N-Shine
7–14 Apr
Home in Cudjoe Key
5.0 out of 5 average rating, 3 reviewsLatitudes-Ocean Front Pool
9–16 Nov
Apartment rentals with a pool
Apartment in Key Colony Beach
4.91 out of 5 average rating, 112 reviewsBeachside Unit 39 Tiki Huts, Private Beach & Pool
22–29 Oct
Apartment in Key West
4.88 out of 5 average rating, 147 reviewsLarge waterfront 2/2 end unit with boat slip
23–30 Aug
Apartment in Key West
4.86 out of 5 average rating, 129 reviewsA Perfect Getaway
12–19 Nov
Apartment in Marathon
4.87 out of 5 average rating, 191 reviewsSombrero Beach Tropical Getaway
10–17 Dec
Apartment in Key West
4.85 out of 5 average rating, 143 reviewsAnchor Drop modern elegance upgrades throughout vi
15–22 Sept
Apartment in Key West
4.83 out of 5 average rating, 243 reviewsLa Dolce Vita, Old Town Steps to Duval! 3 blks bch
6–13 Feb
Apartment in Key West
4.99 out of 5 average rating, 79 reviews*Come to my Deck for a time you won't Forget!
14–21 Aug
Apartment in Marathon
5.0 out of 5 average rating, 6 reviewsOceanside Spacious Studio Escape
11–18 Aug
Quick stats about holiday 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
£88 before taxes and fees
Destinations to explore
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