Waterfront vacation rentals in Sugarloaf Key
Find and book unique waterfront rentals on Airbnb
Top-rated waterfront rentals in Sugarloaf Key
Guests agree: these waterfront rentals 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 Sugarloaf Key waterfront rentals
Waterfront apartment rentals
Apartment in Key West
4.89 out of 5 average rating, 136 reviewsKey West Beachside 1400sf, 2 Bedroom Condo
Oct 6 – 13
Apartment in Key West
4.92 out of 5 average rating, 175 reviewsKW Luxury 2/2 Beachfront resort Tropical Oasis
Sep 4 – 11
Apartment in Key West
4.94 out of 5 average rating, 16 reviewsOceanfront Condo in Key West
Oct 7 – 14
Apartment in Marathon
5.0 out of 5 average rating, 8 reviewsGated Oceanfront Heated Pool
Jul 6 – 13
Apartment in Key West
4.89 out of 5 average rating, 46 reviewsPenthouse in Paradise
Oct 8 – 15
Apartment in Key West
5.0 out of 5 average rating, 4 reviewsPartial ocean view studio with king bed
Apr 12 – 19
Apartment in Marathon
5.0 out of 5 average rating, 5 reviewsMarathon Studio on Lovely Resort w/Amenities
Dec 25 – Jan 1
Apartment in Key Colony Beach
4.83 out of 5 average rating, 78 reviewsBeachside Unit 22 - Private Beach on Atlantic
Jan 3 – 10
Waterfront house rentals
Home in Marathon
4.97 out of 5 average rating, 118 reviewsMarathon one-level home on the Marina - with slip!
Apr 20 – 27
Home in Marathon
4.9 out of 5 average rating, 136 reviewsWaterfront Cozy Modern Retreat w/Deep Canal
Apr 5 – 12
Home in Cudjoe Key
5.0 out of 5 average rating, 7 reviewsVenture Out- Million Dollar Island Resort
Dec 7 – 14
Home in Cudjoe Key
4.94 out of 5 average rating, 17 reviewsMay Extravaganza - Relax in Paradise!
Oct 1 – 8
Home in Cudjoe Key
4.86 out of 5 average rating, 43 reviews*Emerald Seas*-Florida Keys Ocean Front Paradise!
Dec 11 – 18
Home in Cudjoe Key
4.95 out of 5 average rating, 19 reviewsConch Cabana in Paradise 23 miles outside Key West
Mar 22 – 29
Home in Cudjoe Key
4.82 out of 5 average rating, 49 reviewsSpanish Queen @Venture Out
Dec 16 – 23
Home in Cudjoe Key
5.0 out of 5 average rating, 23 reviewsParadise in Cudjoe! Perfect Family Home!
Oct 4 – 11
Waterfront condo rentals
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
Feb 7 – 14
Condo in Key West
4.96 out of 5 average rating, 76 reviewsHidden Beach unit 1 The Perfect Place to stay
Apr 21 – 28
Condo in Key West
4.89 out of 5 average rating, 9 reviewsOcean View Residence
Jun 21 – 28
Condo in Key West
5.0 out of 5 average rating, 29 reviewsGorgeous Ocean View in Paradise
Aug 31 – Sep 7
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
5.0 out of 5 average rating, 7 reviewsOcean Potion NEW 1B/2B 3Balconies Ocean View
Nov 5 – 12
Condo in Key West
5.0 out of 5 average rating, 21 reviewsKey West Condo with Balcony Ocean View
Apr 17 – 24
Destinations to explore
- Key West Vacation rentals
- Varadero Vacation rentals
- Naples Vacation rentals
- Miami Vacation rentals
- Havana Vacation rentals
- Miami Beach Vacation rentals
- Fort Lauderdale Vacation rentals
- Boca Raton Vacation rentals
- West Palm Beach Vacation rentals
- Sarasota Vacation rentals
- Anna Maria Island Vacation rentals
- Tampa Vacation rentals
- Waterfront rentals United States
- Waterfront rentals Florida
- Waterfront rentals Key West
- Waterfront rentals Florida Keys
- Waterfront rentals Marco Island
- Rentals with beach access Sugarloaf Key
- House rentals Sugarloaf Key
- Rentals with a kayak Sugarloaf Key
- Rentals with a washer and dryer Sugarloaf Key
- Rentals with a patio Sugarloaf Key
- Pet-friendly rentals Sugarloaf Key
- Family-friendly rentals Sugarloaf Key
- Rentals with pools Sugarloaf Key
- Monthly Rentals Sugarloaf Key
- Rentals with outdoor seating Sugarloaf Key
- Waterfront rentals Monroe County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom