Waterfront holiday rentals in Cudjoe Key
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Top-rated waterfront rentals in Cudjoe Key
Guests agree: these waterfront rentals are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for waterfront rentals in Cudjoe Key
Waterfront apartment rentals
Flat in Key West
4.89 out of 5 average rating, 136 reviewsKey West Beachside 1400sf, 2 Bedroom Condo
10–17 Dec
Flat in Key West
4.92 out of 5 average rating, 175 reviewsKW Luxury 2/2 Beachfront resort Tropical Oasis
20–27 Dec
Flat in Marathon
5.0 out of 5 average rating, 8 reviewsGated Oceanfront Heated Pool
8–15 Jul
Flat in Key Colony Beach
4.84 out of 5 average rating, 79 reviewsBeachside Unit 22 - Private Beach on Atlantic
17–24 Oct
Flat in Key West
4.94 out of 5 average rating, 16 reviewsOceanfront Condo in Key West
13–20 Dec
Flat in Key West
4.89 out of 5 average rating, 46 reviewsPenthouse in Paradise
30 May – 6 Jun
Flat in Marathon
4.95 out of 5 average rating, 38 reviewsDock POOL Kayaks Bikes Beach2mi WalkToStores
30 Oct – 6 Nov
Flat in Key West
5.0 out of 5 average rating, 4 reviewsPartial ocean view studio with king bed
12–19 Apr
Waterfront house rentals
Home in Marathon
4.99 out of 5 average rating, 107 reviewsSea Ray Cove , 75’ boat dock, 1 block from beach!
5–12 Apr
Home in Marathon
4.9 out of 5 average rating, 137 reviewsWaterfront Cozy Modern Retreat w/Deep Canal
12–19 Apr
Home in Key Colony Beach
4.96 out of 5 average rating, 136 reviewsBeautiful open plan remodeled home in Key Colony
13–20 Nov
Home in Key Colony Beach
4.81 out of 5 average rating, 132 reviewsWaterview from three sides, Cabana Club, 30' Docks
6–13 Mar
Home in Cudjoe Key
4.87 out of 5 average rating, 46 reviews*Emerald Seas*-Florida Keys Ocean Front Paradise!
25 Jun – 2 Jul
Home in Cudjoe Key
4.86 out of 5 average rating, 28 reviewsKeys Island Villa - Venture Out Home 354
11–18 Oct
Home in Cudjoe Key
4.83 out of 5 average rating, 6 reviewsSailfish Haven
19–26 Sep
Home in Cudjoe Key
4.82 out of 5 average rating, 49 reviewsSpanish Queen @Venture Out
16–23 Dec
Waterfront apartment rentals
Apartment in Key West
4.89 out of 5 average rating, 148 reviewsLarge waterfront 2/2 end unit with boat slip
14–21 Dec
Apartment in Key West
4.85 out of 5 average rating, 143 reviewsAnchor Drop modern elegance upgrades throughout vi
10–17 Mar
Apartment in Key West
4.83 out of 5 average rating, 243 reviewsLa Dolce Vita, Old Town Steps to Duval! 3 blks bch
24 Apr – 1 May
Apartment in Key Colony Beach
5.0 out of 5 average rating, 27 reviewsSea-Esta Condo beach and pool
9–16 Nov
Apartment in Marathon
4.97 out of 5 average rating, 74 reviewsNAUTI HIDEAWAY-Deep Slip/Ramp/Trailer Parking/Pool
7–14 Apr
Apartment in Key West
4.96 out of 5 average rating, 76 reviewsHidden Beach unit 1 The Perfect Place to stay
27 Nov – 4 Dec
Apartment in Marathon
4.93 out of 5 average rating, 15 reviewsParadise Palms NEW 1B/2B Desk; Pool; Balcony
1–8 Aug
Apartment in Key West
5.0 out of 5 average rating, 30 reviewsGorgeous Ocean View in Paradise
31 Aug – 7 Sep
Quick stats about waterfront rentals in Cudjoe Key
Total rentals
110 properties
Rentals with a pool
80 properties have a pool
Pet-friendly rentals
40 properties allow pets
Family-friendly rentals
90 properties are a good fit for families
Total number of reviews
2.3K reviews
Nightly prices starting at
$149 SGD before taxes and fees
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