Waterfront holiday rentals in Sugarloaf Key
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Top-rated waterfront accommodation in Sugarloaf Key
Guests agree: These waterfront accommodation options 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 Sugarloaf Key waterfront rentals
Waterfront apartment accommodation
Apartment in Key Largo
4.92 out of 5 average rating, 231 reviewsWaterfront Studio 2| Couples Oasis | Kayaks | Pool
7–14 Dec
Apartment in Key West
4.89 out of 5 average rating, 136 reviewsKey West Beachside 1400sf, 2 Bedroom Condo
10–17 Dec
Apartment in Key West
4.92 out of 5 average rating, 175 reviewsKW Luxury 2/2 Beachfront resort Tropical Oasis
8–15 Dec
Apartment in Tavernier
4.95 out of 5 average rating, 149 reviewsBoho FL Keys Condo
10–17 Oct
Apartment in Key Largo
4.75 out of 5 average rating, 186 reviewsHideaway with Picturesque Canal View Apt 3
6–13 Jun
Apartment in Key Largo
4.98 out of 5 average rating, 126 reviewsKey Largo Kawama Lagoon Free Cancel Deutsch Spain
15–22 Aug
Apartment in Key Largo
4.92 out of 5 average rating, 106 reviews2/1 Oceanfront Apartment with Dockage
10–17 Apr
Apartment in Tavernier
4.83 out of 5 average rating, 255 reviewsBreathtaking Oceanfront Views at Tropical Daze
15–22 Jul
Waterfront house rentals
Home in Marathon
4.97 out of 5 average rating, 118 reviewsMarathon one-level home on the Marina - with slip!
20–27 Dec
Home in Upper Sugarloaf Key
4.87 out of 5 average rating, 46 reviewsBungalows at Sugarloaf Beach - The Lighthouse
28 Oct – 4 Nov
Home in Cudjoe Key
5.0 out of 5 average rating, 7 reviewsVenture Out- Million Dollar Island Resort
7–14 Dec
Home in Cudjoe Key
4.87 out of 5 average rating, 45 reviews*Emerald Seas*-Florida Keys Ocean Front Paradise!
3–10 Mar
Home in Cudjoe Key
4.82 out of 5 average rating, 49 reviewsSpanish Queen @Venture Out
6–13 Jan
Home in Cudjoe Key
4.95 out of 5 average rating, 19 reviewsConch Cabana in Paradise 23 miles outside Key West
13–20 Jan
Home in Cudjoe Key
4.94 out of 5 average rating, 17 reviewsMay Extravaganza - Relax in Paradise!
1–8 Oct
Home in Cudjoe Key
5.0 out of 5 average rating, 23 reviewsParadise in Cudjoe! Perfect Family Home!
4–11 Oct
Waterfront condo accommodation
Condo in Key Colony Beach
4.91 out of 5 average rating, 112 reviewsBeachside Unit 39 Tiki Huts, Private Beach & Pool
27 Oct – 3 Nov
Condo in Tavernier
4.95 out of 5 average rating, 108 reviewsKey Largo Coastal Condo-Ocean View ~ Pool ~ Beach
21–28 Sep
Condo in Tavernier
4.96 out of 5 average rating, 159 reviewsBest View Ocean Pointe Pool Beach King Bed, Gated
1–8 Apr
Condo in Key West
4.85 out of 5 average rating, 143 reviewsAnchor Drop modern elegance upgrades throughout vi
10–17 Mar
Condo in Tavernier
4.98 out of 5 average rating, 142 reviewsOcean Views at Ocean Pointe
22–29 Apr
Condo in Key Largo
4.98 out of 5 average rating, 116 reviewsOceanfront Condo w/Lake, Kayak, Paddleboard & Bike
2–9 Nov
Condo in Tavernier
4.93 out of 5 average rating, 135 reviewsIt's Tiki Time! Top Floor SeaView Mid-Mod 1 Br/1Ba
20–27 Feb
Condo 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
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- Rentals with outdoor seating Sugarloaf Key
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