Sugarloaf Key Luxury Vacation Rentals
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Best-rated
Key West Villas
- Cookware/ Kitchen utensils
-
Car park
US$ 15 per day
- Express check-in/ -out
- Air conditioning
- Live entertainment
- Outdoor swimming pool
Located just 6 minutes' stroll from The Ernest Hemingway Home and Museum, the 7-room Key West Villas provides an outdoor swimming pool as well as snorkelling to diversify guests' leisure. The Key West villa is nestled in Duval with one of Key West's top culinary experiences, offering a Jacuzzi to ensure a relaxing stay.
The property offers bicycles for rent, as well as access to a sunbathing terrace, a shared lounge, and a golf course to ensure an interesting stay.
Key West Villas
- Cookware/ Kitchen utensils
-
Car park
US$ 15 per day
- Express check-in/ -out
- Air conditioning
- Live entertainment
- Outdoor swimming pool
Key West Villas
Located just 6 minutes' stroll from The Ernest Hemingway Home and Museum, the 7-room Key West Villas provides an outdoor swimming pool as well as snorkelling to diversify guests' leisure. The Key West villa is nestled in Duval with one of Key West's top culinary experiences, offering a Jacuzzi to ensure a relaxing stay.
The property offers bicycles for rent, as well as access to a sunbathing terrace, a shared lounge, and a golf course to ensure an interesting stay.
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Guest favorite
Sugarloaf Key Rv Resort & Cottages
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Bar/ Lounge area
- Outdoor swimming pool
Nestled 2 km from Bow Channel, Sugarloaf Key Rv Resort & Cottages Summerland Key is boasting a patio and barbecue for guests' enjoyment. Providing guests with Wi-Fi and a car park, the villa is 10 minutes' drive from Gopher Key.
Sugarloaf Key Rv Resort & Cottages
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Bar/ Lounge area
- Outdoor swimming pool
Sugarloaf Key Rv Resort & Cottages
Nestled 2 km from Bow Channel, Sugarloaf Key Rv Resort & Cottages Summerland Key is boasting a patio and barbecue for guests' enjoyment. Providing guests with Wi-Fi and a car park, the villa is 10 minutes' drive from Gopher Key.
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Great deal
Tropical Cottages
- BBQ facilities
- Free parking
- Express check-in/ -out
- Air conditioning
- Bar/ Lounge area
- Patio
Located nearly a 10-minute ride from The Turtle Hospital, Tropical Cottages Marathon provides access to various tourist attractions in the vicinity.
Tropical Cottages
- BBQ facilities
- Free parking
- Express check-in/ -out
- Air conditioning
- Bar/ Lounge area
- Patio
Tropical Cottages
Located nearly a 10-minute ride from The Turtle Hospital, Tropical Cottages Marathon provides access to various tourist attractions in the vicinity.
Cheap Vacation Rentals in Sugarloaf Key Florida
Old Wooden Bridge Resort & Marina
- BBQ facilities
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Pool with view
Featuring a sunbathing terrace, water slides, and a picnic area for a delightful experience, Old Wooden Bridge Resort & Marina Big Pine Key villa offers a convenient location nearly a 5-minute walk from Old Wooden Bridge Marina. Guests can enjoy canyoning, boating, and volleyball at the property, located 2.2 km from No Name Key.
Guests can also unwind in a fence-around pool, while enjoying views over the sun terrace.
Old Wooden Bridge Resort & Marina
- BBQ facilities
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Pool with view
Old Wooden Bridge Resort & Marina
Featuring a sunbathing terrace, water slides, and a picnic area for a delightful experience, Old Wooden Bridge Resort & Marina Big Pine Key villa offers a convenient location nearly a 5-minute walk from Old Wooden Bridge Marina. Guests can enjoy canyoning, boating, and volleyball at the property, located 2.2 km from No Name Key.
Guests can also unwind in a fence-around pool, while enjoying views over the sun terrace.
Sailors Cabin - Prime Downtown Key West Spot - Walk To Duval
- Picnic area/ Tables
- Free parking
- VIP check-in/ -out
- Flat-screen TV
- Heating
- Terrace
The 1-bedroom Sailors Cabin - Prime Downtown Key West Spot - Walk To Duval boasts a central location approximately 700 metres from Key West Butterfly and Nature Conservatory. The apartment capacity is based on up to 2 guests.
Sailors Cabin - Prime Downtown Key West Spot - Walk To Duval
- Picnic area/ Tables
- Free parking
- VIP check-in/ -out
- Flat-screen TV
- Heating
- Terrace
Sailors Cabin - Prime Downtown Key West Spot - Walk To Duval
The 1-bedroom Sailors Cabin - Prime Downtown Key West Spot - Walk To Duval boasts a central location approximately 700 metres from Key West Butterfly and Nature Conservatory. The apartment capacity is based on up to 2 guests.
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Private beach
Aqua Lodges At 47Th Street
- Cookware/ Kitchen utensils
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Sun loungers
Up to 5 guests can stay at Aqua Lodges At 47Th Street Marathon and enjoy Tilden's Scuba Center, located 5 minutes' walk away. Providing guests with Wi-Fi and private car parking, this 7-room lodge is 2.8 km from Sombrero Beach.
Aqua Lodges At 47Th Street
- Cookware/ Kitchen utensils
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Sun loungers
Aqua Lodges At 47Th Street
Up to 5 guests can stay at Aqua Lodges At 47Th Street Marathon and enjoy Tilden's Scuba Center, located 5 minutes' walk away. Providing guests with Wi-Fi and private car parking, this 7-room lodge is 2.8 km from Sombrero Beach.
Pet Friendly Vacation Rentals Sugarloaf Key Florida
The Bartlum-Luxurious Studio
- Cookware/ Kitchen utensils
- Air conditioning
- Flat-screen TV
The 51 m² The Bartlum-Luxurious Studio Key West is nestled in the Downtown Key West district, about a 5-minute walk from the seafood restaurant Fogarty's. Wi-Fi and a car park are among the essentials at guests' disposal.
The Bartlum-Luxurious Studio
- Cookware/ Kitchen utensils
- Air conditioning
- Flat-screen TV
The Bartlum-Luxurious Studio
The 51 m² The Bartlum-Luxurious Studio Key West is nestled in the Downtown Key West district, about a 5-minute walk from the seafood restaurant Fogarty's. Wi-Fi and a car park are among the essentials at guests' disposal.
Eleuthera - 2X2 Fully Updated Old Town Waterfront Corner Condo
- BBQ facilities
- Free parking
- Air conditioning
- Ironing facilities
- Golf centre
- Outdoor swimming pool
Featuring a swimming pool, the 2-bedroom Eleuthera - 2X2 Fully Updated Old Town Waterfront Corner Condo Key West villa is located around 5 minutes' walk from Bayview Park and is suitable for up to 8 guests. The accommodation features opportunities for cycling and fisheries in the area, just 1.9 km from San Carlos Institute.
Eleuthera - 2X2 Fully Updated Old Town Waterfront Corner Condo
- BBQ facilities
- Free parking
- Air conditioning
- Ironing facilities
- Golf centre
- Outdoor swimming pool
Eleuthera - 2X2 Fully Updated Old Town Waterfront Corner Condo
Featuring a swimming pool, the 2-bedroom Eleuthera - 2X2 Fully Updated Old Town Waterfront Corner Condo Key West villa is located around 5 minutes' walk from Bayview Park and is suitable for up to 8 guests. The accommodation features opportunities for cycling and fisheries in the area, just 1.9 km from San Carlos Institute.
Studio Blue
- Cookware/ Kitchen utensils
- Flat-screen TV
- Tea and coffee facilities
- Patio
Situated in the very heart of Key West, Studio Blue Key West is just 6 minutes' stroll from the Key West Firehouse Museum. The apartment features a patio which opens out onto the garden.
Studio Blue
- Cookware/ Kitchen utensils
- Flat-screen TV
- Tea and coffee facilities
- Patio
Studio Blue
Situated in the very heart of Key West, Studio Blue Key West is just 6 minutes' stroll from the Key West Firehouse Museum. The apartment features a patio which opens out onto the garden.
Sugarloaf Key Vacation Rentals Oceanfront
Rose Lane Villas
- Cookware/ Kitchen utensils
-
Car park
US$ 25 per day
- Concierge desk
- Air conditioning
- Flat-screen TV
- Heated swimming pool
The 6-room Rose Lane Villas Key West is situated around a 5-minute walk from the vintage parish "Saint Paul's Episcopal Church of Key West", featuring such comforts as Wi-Fi and private car parking. Providing a heated outdoor swimming pool, this accommodation also offers windsurfing, snorkelling, and diving for active guests.
Rose Lane Villas
- Cookware/ Kitchen utensils
-
Car park
US$ 25 per day
- Concierge desk
- Air conditioning
- Flat-screen TV
- Heated swimming pool
Rose Lane Villas
The 6-room Rose Lane Villas Key West is situated around a 5-minute walk from the vintage parish "Saint Paul's Episcopal Church of Key West", featuring such comforts as Wi-Fi and private car parking. Providing a heated outdoor swimming pool, this accommodation also offers windsurfing, snorkelling, and diving for active guests.
Yellowfin Ledge
- Tea and coffee facilities
Staying at the 1-bedroom Yellowfin Ledge Key West villa, guests can easily reach the fully accredited Mel Fisher Maritime Heritage Museum, located only 1.4 km away. With a maximum capacity of 3 guests, the Key West holiday home offers parking.
Yellowfin Ledge
- Tea and coffee facilities
Yellowfin Ledge
Staying at the 1-bedroom Yellowfin Ledge Key West villa, guests can easily reach the fully accredited Mel Fisher Maritime Heritage Museum, located only 1.4 km away. With a maximum capacity of 3 guests, the Key West holiday home offers parking.
Grand Marina Suite -Waterfront Condo
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Ironing facilities
- Fitness centre
- Outdoor swimming pool
Up to 6 guests can stay at the 3-room Grand Marina Suite -Waterfront Condo Key West villa and enjoy Key West Harbour, located approximately 5 minutes' walk away. This 2-bedroom holiday home features opportunities for cycling and fisheries in the area, 2.5 km from Key West Golf Club.
The availability of fitness classes, along with a fitness room, ensures guests an active stay.
Grand Marina Suite -Waterfront Condo
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Ironing facilities
- Fitness centre
- Outdoor swimming pool
Grand Marina Suite -Waterfront Condo
Up to 6 guests can stay at the 3-room Grand Marina Suite -Waterfront Condo Key West villa and enjoy Key West Harbour, located approximately 5 minutes' walk away. This 2-bedroom holiday home features opportunities for cycling and fisheries in the area, 2.5 km from Key West Golf Club.
The availability of fitness classes, along with a fitness room, ensures guests an active stay.
Sugarloaf Key Vacation Rentals with Private Pool
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Private beach
Nautilus...Ocean Front Cottage Retreat ~
- BBQ facilities
- Free parking
- 24-hour security
- Air conditioning
- Tennis court
- Pool with view
Hosting up to 6 guests, the 2-bedroom Nautilus..Ocean Front Cottage Retreat ~ Cudjoe Key is nestled in a beach area, about a 10-minute drive from Summerland Key Island. Guests can enjoy snorkelling, canyoning, and fisheries at this Cudjoe Key villa, located 2.5 km from Sunrise Beach Resort.
The presence of a heated pool, a Jacuzzi ensures a relaxing stay.
Nautilus...Ocean Front Cottage Retreat ~
- BBQ facilities
- Free parking
- 24-hour security
- Air conditioning
- Tennis court
- Pool with view
Nautilus...Ocean Front Cottage Retreat ~
Hosting up to 6 guests, the 2-bedroom Nautilus..Ocean Front Cottage Retreat ~ Cudjoe Key is nestled in a beach area, about a 10-minute drive from Summerland Key Island. Guests can enjoy snorkelling, canyoning, and fisheries at this Cudjoe Key villa, located 2.5 km from Sunrise Beach Resort.
The presence of a heated pool, a Jacuzzi ensures a relaxing stay.
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Top location
Sugarloaf Lodge
- Restaurant
- Free parking
- Air conditioning
- Flat-screen TV
- Entertainment
- Outdoor swimming pool
Sugarloaf Lodge Sugarloaf Shores is located merely 0.9 km from the wooden SkyDive Keywest Tower and allows guests to enjoy skydiving, snorkelling, and kayaking. Offering an outdoor swimming pool, this Sugarloaf Shores lodge invites guests to visit Old Finds Bight, located about a 10-minute ride away.
Sugarloaf Lodge
- Restaurant
- Free parking
- Air conditioning
- Flat-screen TV
- Entertainment
- Outdoor swimming pool
Sugarloaf Lodge
Sugarloaf Lodge Sugarloaf Shores is located merely 0.9 km from the wooden SkyDive Keywest Tower and allows guests to enjoy skydiving, snorkelling, and kayaking. Offering an outdoor swimming pool, this Sugarloaf Shores lodge invites guests to visit Old Finds Bight, located about a 10-minute ride away.
Ma159 Tarpon Breeze
- BBQ facilities
- Flat-screen TV
- Laundry
- Tea and coffee facilities
- Golf centre
- Pool with view
Staying at the 1-bedroom Ma159 Tarpon Breeze Villa Marathon, guests can easily reach Conch-Air Florida Keys Scenic Flights, located nearly a 25-minute walk away. Guests can enjoy cycling and fisheries at the Marathon villa, located only 1.3 km from San Pablo Catholic Church.
An outdoor swimming pool, as well as access to a picnic area and a golf course are available at the Marathon property.
Ma159 Tarpon Breeze
- BBQ facilities
- Flat-screen TV
- Laundry
- Tea and coffee facilities
- Golf centre
- Pool with view
Ma159 Tarpon Breeze
Staying at the 1-bedroom Ma159 Tarpon Breeze Villa Marathon, guests can easily reach Conch-Air Florida Keys Scenic Flights, located nearly a 25-minute walk away. Guests can enjoy cycling and fisheries at the Marathon villa, located only 1.3 km from San Pablo Catholic Church.
An outdoor swimming pool, as well as access to a picnic area and a golf course are available at the Marathon property.
Casa Blue Pelican.
- BBQ facilities
- Free parking
- Security
- Air conditioning
- Billiard tables
- Sun terrace
Casa Blue Pelican. Marathon is located merely a 6-minute walk from Florida Keys Aquarium Encounters and offers a Jacuzzi, ensuring guests a relaxing stay. This 3-bedroom villa features opportunities for canyoning, ping pong, and fisheries in the area, not far from Eaa Air Museum.
There are bicycles to keep up with active daily routine.
Casa Blue Pelican.
- BBQ facilities
- Free parking
- Security
- Air conditioning
- Billiard tables
- Sun terrace
Casa Blue Pelican.
Casa Blue Pelican. Marathon is located merely a 6-minute walk from Florida Keys Aquarium Encounters and offers a Jacuzzi, ensuring guests a relaxing stay. This 3-bedroom villa features opportunities for canyoning, ping pong, and fisheries in the area, not far from Eaa Air Museum.
There are bicycles to keep up with active daily routine.
Blue Ocean Bungalow
- Cookware/ Kitchen utensils
- Free parking
- Security
- Air conditioning
- Golf centre
- Terrace
During the stay at Blue Ocean Bungalow Marathon, guests can indulge in canyoning and fisheries or visit Spirit Snorkeling, located a 14-minute walk away. The 3-bedroom holiday home boasts a terrace and a golf course, while the 63 - acre Crane Point Museum and Nature Center is 2.5 km away.
Blue Ocean Bungalow
- Cookware/ Kitchen utensils
- Free parking
- Security
- Air conditioning
- Golf centre
- Terrace
Blue Ocean Bungalow
During the stay at Blue Ocean Bungalow Marathon, guests can indulge in canyoning and fisheries or visit Spirit Snorkeling, located a 14-minute walk away. The 3-bedroom holiday home boasts a terrace and a golf course, while the 63 - acre Crane Point Museum and Nature Center is 2.5 km away.
Ma178 Green Pineapple
- BBQ facilities
- Flat-screen TV
- Laundry
- Tea and coffee facilities
- Pool with view
- Outdoor swimming pool
Staying at the 1-bedroom Ma178 Green Pineapple Marathon villa, guests can visit Conch-Air Florida Keys Scenic Flights, which is nearly a 25-minute walk away. Providing opportunities for cycling and fisheries, the Marathon holiday home can accommodate 4 guests and also boasts an outdoor swimming pool for extra relaxation.
Ma178 Green Pineapple
- BBQ facilities
- Flat-screen TV
- Laundry
- Tea and coffee facilities
- Pool with view
- Outdoor swimming pool
Ma178 Green Pineapple
Staying at the 1-bedroom Ma178 Green Pineapple Marathon villa, guests can visit Conch-Air Florida Keys Scenic Flights, which is nearly a 25-minute walk away. Providing opportunities for cycling and fisheries, the Marathon holiday home can accommodate 4 guests and also boasts an outdoor swimming pool for extra relaxation.
Carney'S Reef New 1B 1B Pool Patio
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Ironing facilities
- Golf centre
- Outdoor swimming pool
Located just 1.9 km from Conch-Air Florida Keys Scenic Flights, the 1-bedroom Carney'S Reef New 1B 1B Pool Patio Villa Marathon has an outdoor swimming pool and is ideal for up to 4 guests. Guests can enjoy cycling and fisheries at this Marathon holiday home, located in proximity to the snug Sunset Park Beach.
Carney'S Reef New 1B 1B Pool Patio
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Ironing facilities
- Golf centre
- Outdoor swimming pool
Carney'S Reef New 1B 1B Pool Patio
Located just 1.9 km from Conch-Air Florida Keys Scenic Flights, the 1-bedroom Carney'S Reef New 1B 1B Pool Patio Villa Marathon has an outdoor swimming pool and is ideal for up to 4 guests. Guests can enjoy cycling and fisheries at this Marathon holiday home, located in proximity to the snug Sunset Park Beach.
Kw23 Atlantic Ocean View
- Cookware/ Kitchen utensils
- Ironing facilities
- Tea and coffee facilities
Located about a 20-minute walk from Bayview Park, the 126 m² Kw23 Atlantic Ocean View Apartment Key West is 3.1 km from a top family-friendly place like Key West Aquarium. Wi-Fi and parking are provided for guests' business or leisure needs.
Kw23 Atlantic Ocean View
- Cookware/ Kitchen utensils
- Ironing facilities
- Tea and coffee facilities
Kw23 Atlantic Ocean View
Located about a 20-minute walk from Bayview Park, the 126 m² Kw23 Atlantic Ocean View Apartment Key West is 3.1 km from a top family-friendly place like Key West Aquarium. Wi-Fi and parking are provided for guests' business or leisure needs.
Are you in a hurry?
Here is a quick list of Vacation Rentals in Sugarloaf Key, selected based on their rating
| Name of hotel | Accommodation Rating | Price, $ | |
| Key West Villas |
9.7 / 10 (281 Reviews) |
From 219$ | |
| Sugarloaf Key Rv Resort & Cottages |
9.1 / 10 (602 Reviews) |
From 359$ | |
| Tropical Cottages |
7.9 / 10 (425 Reviews) |
From 83$ | |
| Old Wooden Bridge Resort & Marina |
8.0 / 10 (328 Reviews) |
From 149$ | |
| Sailors Cabin - Prime Downtown Key West Spot - Walk To Duval |
9.1 / 10 (34 Reviews) |
From 228$ |
Frequently Asked Questions
What are some budget-friendly vacation rentals in Sugarloaf Key?
Tropical Cottages and Old Wooden Bridge Resort & Marina offer budget-friendly options for visitors. These rentals provide a comfortable stay without breaking the bank on your trip.
Book your stay during the off-peak season from September to November for lower rates and fewer crowds.
Which vacation rentals offer space for families in Sugarloaf Key?
Sugarloaf Lodge and Sugarloaf Key RV Resort & Cottages provide spacious options for families. These rentals feature multiple bedrooms and family-oriented amenities.
Consider booking accommodations with kitchens, so you can prepare meals and save on dining costs with kids.
Can I find vacation rentals with a pool in Sugarloaf Key?
Blue Ocean Bungalow and Grand Marina Suite - Waterfront Condo both offer pool access. Enjoy relaxation and family fun right outside your door.
Visit the pool early in the day for a quieter experience, especially during weekends.
Which vacation rentals have beautiful ocean views in Sugarloaf Key?
Kw23 Atlantic Ocean View and Nautilus Ocean Front Cottage Retreat provide stunning coastal views. Enjoy the beauty of the ocean right from your rental.
Book a rental with a balcony to enjoy sunsets and fresh air without leaving your unit.
Are there vacation rentals that allow pets in Sugarloaf Key?
Sugarloaf Key RV Resort & Cottages is a pet-friendly option. Bring your furry friends along to enjoy your vacation together.
Confirm the pet policy in advance and consider pet-friendly parks nearby, like the Sugarloaf Key and adjacent beaches.
What rentals are ideal for couples in Sugarloaf Key?
Rose Lane Villas and Casa Blue Pelican offer romantic settings for couples. Enjoy privacy and intimate spaces perfect for a getaway.
Look for units with outdoor patios for evening relaxation under the stars.
Where can I find vacation rentals near the beach in Sugarloaf Key?
Blue Ocean Bungalow and Nautilus Ocean Front Cottage Retreat are both a short walk from the beach. Experience sun, sand, and fun in the water.
Pack snorkeling gear to fully enjoy the local marine life when visiting the nearby beaches.
What seasonal events occur in Sugarloaf Key?
In December, the Sugarloaf Key Holiday Festival showcases lights, boat parades, and local festivities. Enjoy activities and entertainment that bring the community together.
Plan to visit during December to fully immerse in the holiday spirit and enjoy themed decorations throughout the area.
How can I navigate Sugarloaf Key effectively?
Driving is the best way to navigate Sugarloaf Key, as public transport options are limited. Renting a car can give you the freedom to explore the surrounding islands.
Consider downloading a map app on your phone to help find local attractions and avoid getting lost.
What should I pack for a trip to Sugarloaf Key?
Pack swimwear, sunscreen, and light clothing for warm temperatures. Bring comfortable shoes for walking and outdoor activities.
Don't forget insect repellent, especially if you plan to explore nature reserves or go out in the evening.