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
Situated just 6 minutes' stroll from Mile Marker 0 Store, the 7-room Key West Villas includes a swimming pool, as well as a Jacuzzi to relax in. Nestled in Duval with one of Key West's top culinary experiences, the Key West villa offers guided snorkelling trips and ecotours to diversify guests' leisure.
Guests can explore the area with bicycles offered for rent onsite, where snorkelling are possible for sport lovers.
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
Situated just 6 minutes' stroll from Mile Marker 0 Store, the 7-room Key West Villas includes a swimming pool, as well as a Jacuzzi to relax in. Nestled in Duval with one of Key West's top culinary experiences, the Key West villa offers guided snorkelling trips and ecotours to diversify guests' leisure.
Guests can explore the area with bicycles offered for rent onsite, where snorkelling are possible for sport lovers.
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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
Sugarloaf Key Rv Resort & Cottages Summerland Key is located 2 km from the Bow Channel and provides canoeing and fishing for active guests.
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
Sugarloaf Key Rv Resort & Cottages Summerland Key is located 2 km from the Bow Channel and provides canoeing and fishing for active guests.
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Great deal
Tropical Cottages
- BBQ facilities
- Free parking
- Express check-in/ -out
- Air conditioning
- Bar/ Lounge area
- Patio
Staying at Tropical Cottages Marathon, guests can easily reach The Turtle Hospital, located nearly a 10-minute ride away.
Tropical Cottages
- BBQ facilities
- Free parking
- Express check-in/ -out
- Air conditioning
- Bar/ Lounge area
- Patio
Tropical Cottages
Staying at Tropical Cottages Marathon, guests can easily reach The Turtle Hospital, located nearly a 10-minute ride away.
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
Old Wooden Bridge Resort & Marina Big Pine Key villa is located about 25 minutes' walk from No Name Key and provides canoeing, boating, and cycling for active guests.
Guests can rent boats to explore the local area, while there is also a fenced pool on site.
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
Old Wooden Bridge Resort & Marina Big Pine Key villa is located about 25 minutes' walk from No Name Key and provides canoeing, boating, and cycling for active guests.
Guests can rent boats to explore the local area, while there is also a fenced pool on site.
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-room Sailors Cabin - Prime Downtown Key West Spot - Walk To Duval boasts a central location approximately 700 metres from the Key West Butterfly and Nature Conservatory. The apartment sleeps up to 2 guests and features Wi-Fi, and bicycles for rent.
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-room Sailors Cabin - Prime Downtown Key West Spot - Walk To Duval boasts a central location approximately 700 metres from the Key West Butterfly and Nature Conservatory. The apartment sleeps up to 2 guests and features Wi-Fi, and bicycles for rent.
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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
Overlooking the sea, Aqua Lodges At 47Th Street Marathon enjoys a beachfront setting 5 minutes' walk from Tilden's Scuba Center. Located 2.8 km from the Sombrero Beach, this 7-room lodge provides Wi-Fi and private parking.
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
Overlooking the sea, Aqua Lodges At 47Th Street Marathon enjoys a beachfront setting 5 minutes' walk from Tilden's Scuba Center. Located 2.8 km from the Sombrero Beach, this 7-room lodge provides Wi-Fi and private parking.
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 situated merely 5 minutes' walk from Nancy Forrester's Secret Garden and 5 km from Key West International airport. The maximum occupancy at this 1-bedroom apartment is 4 guests.
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 situated merely 5 minutes' walk from Nancy Forrester's Secret Garden and 5 km from Key West International airport. The maximum occupancy at this 1-bedroom apartment is 4 guests.
Eleuthera - 2X2 Fully Updated Old Town Waterfront Corner Condo
- BBQ facilities
- Free parking
- Air conditioning
- Ironing facilities
- Golf centre
- Outdoor swimming pool
The 2-bedroom Eleuthera - 2X2 Fully Updated Old Town Waterfront Corner Condo Key West villa is situated around 5 minutes' walk from the Bayview Park, featuring such comforts as high-speed Internet access and private car parking. Suitable for up to 8 guests, the accommodation offers opportunities for cycling and fishing.
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
The 2-bedroom Eleuthera - 2X2 Fully Updated Old Town Waterfront Corner Condo Key West villa is situated around 5 minutes' walk from the Bayview Park, featuring such comforts as high-speed Internet access and private car parking. Suitable for up to 8 guests, the accommodation offers opportunities for cycling and fishing.
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
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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 located nearly a 25-minute walk from the Higgs Beach Dog Park and provides a heated outdoor swimming pool, ensuring a relaxing stay. Situated in Duval with one of Key West's top culinary experiences, this accommodation features private car parking on site.
A range of activities, such as windsurfing, snorkelling, and diving, is arranged on site.
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 located nearly a 25-minute walk from the Higgs Beach Dog Park and provides a heated outdoor swimming pool, ensuring a relaxing stay. Situated in Duval with one of Key West's top culinary experiences, this accommodation features private car parking on site.
A range of activities, such as windsurfing, snorkelling, and diving, is arranged on site.
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.
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.
Grand Marina Suite -Waterfront Condo
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Ironing facilities
- Fitness centre
- Outdoor swimming pool
The 2-bedroom Grand Marina Suite -Waterfront Condo Key West villa provides easy access to various city attractions, such as Key West Harbour, situated approximately 5 minutes' walk away. Suitable for up to 6 guests, this property offers opportunities for cycling and fishing.
Grand Marina Suite -Waterfront Condo
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Ironing facilities
- Fitness centre
- Outdoor swimming pool
Grand Marina Suite -Waterfront Condo
The 2-bedroom Grand Marina Suite -Waterfront Condo Key West villa provides easy access to various city attractions, such as Key West Harbour, situated approximately 5 minutes' walk away. Suitable for up to 6 guests, this property offers opportunities for cycling and fishing.
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
Offering a Jacuzzi, the 2-bedroom Nautilus..Ocean Front Cottage Retreat ~ Cudjoe Key is located about a 10-minute drive from Summerland Key. With a maximum capacity of 6 guests, this Cudjoe Key villa offers private car parking.
Guests can enjoy snorkelling, canoeing, and fishing offered on site.
Nautilus...Ocean Front Cottage Retreat ~
- BBQ facilities
- Free parking
- 24-hour security
- Air conditioning
- Tennis court
- Pool with view
Nautilus...Ocean Front Cottage Retreat ~
Offering a Jacuzzi, the 2-bedroom Nautilus..Ocean Front Cottage Retreat ~ Cudjoe Key is located about a 10-minute drive from Summerland Key. With a maximum capacity of 6 guests, this Cudjoe Key villa offers private car parking.
Guests can enjoy snorkelling, canoeing, and fishing offered on site.
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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. Featuring boat rentals, this Sugarloaf Shores lodge invites guests to visit the Old Finds Bight, situated about a 10-minute ride away.
The property offers guests to enjoy guided snorkelling trips, or relax by a swimming pool.
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. Featuring boat rentals, this Sugarloaf Shores lodge invites guests to visit the Old Finds Bight, situated about a 10-minute ride away.
The property offers guests to enjoy guided snorkelling trips, or relax by a swimming pool.
Ma159 Tarpon Breeze
- BBQ facilities
- Flat-screen TV
- Laundry
- Tea and coffee facilities
- Golf centre
- Pool with view
Staying at Ma159 Tarpon Breeze Villa Marathon, guests can visit Conch-Air Florida Keys Scenic Flights, which is nearly a 25-minute walk away. Guests can enjoy cycling and fishing at the Marathon villa, located only 1.3 km from the San Pablo Catholic Church.
Ma159 Tarpon Breeze
- BBQ facilities
- Flat-screen TV
- Laundry
- Tea and coffee facilities
- Golf centre
- Pool with view
Ma159 Tarpon Breeze
Staying at Ma159 Tarpon Breeze Villa Marathon, guests can visit Conch-Air Florida Keys Scenic Flights, which is nearly a 25-minute walk away. Guests can enjoy cycling and fishing at the Marathon villa, located only 1.3 km from the San Pablo Catholic Church.
Casa Blue Pelican.
- BBQ facilities
- Free parking
- Security
- Air conditioning
- Billiard tables
- Sun terrace
Offering a Jacuzzi, Casa Blue Pelican. Marathon is situated merely a 6-minute walk from the 63 - acre Crane Point Museum and Nature Center and can accommodate 8 people. This 3-bedroom villa features opportunities for canoeing, ping-pong, and fishing in the area, not far from the EAA Air Museum.
Fitness facilities feature bicycles.
Casa Blue Pelican.
- BBQ facilities
- Free parking
- Security
- Air conditioning
- Billiard tables
- Sun terrace
Casa Blue Pelican.
Offering a Jacuzzi, Casa Blue Pelican. Marathon is situated merely a 6-minute walk from the 63 - acre Crane Point Museum and Nature Center and can accommodate 8 people. This 3-bedroom villa features opportunities for canoeing, ping-pong, and fishing in the area, not far from the EAA Air Museum.
Fitness facilities feature bicycles.
Blue Ocean Bungalow
- Cookware/ Kitchen utensils
- Free parking
- Security
- Air conditioning
- Golf centre
- Terrace
Blue Ocean Bungalow Marathon is located merely a 5-minute walk from The Turtle Hospital and offers guests to enjoy canoeing and fishing. Located 2.5 km from the 63-acre Crane Point Museum and Nature Center, the 3-bedroom holiday home provides Wi-Fi and private parking.
Blue Ocean Bungalow
- Cookware/ Kitchen utensils
- Free parking
- Security
- Air conditioning
- Golf centre
- Terrace
Blue Ocean Bungalow
Blue Ocean Bungalow Marathon is located merely a 5-minute walk from The Turtle Hospital and offers guests to enjoy canoeing and fishing. Located 2.5 km from the 63-acre Crane Point Museum and Nature Center, the 3-bedroom holiday home provides Wi-Fi and private parking.
Ma178 Green Pineapple
- BBQ facilities
- Flat-screen TV
- Laundry
- Tea and coffee facilities
- Pool with view
- Outdoor swimming pool
Staying at Ma178 Green Pineapple Marathon villa, guests can visit Conch-Air Florida Keys Scenic Flights, which is nearly a 25-minute walk away. Guests can enjoy cycling and fishing at the Marathon holiday home, located only 1.3 km from the San Pablo Catholic Church.
Ma178 Green Pineapple
- BBQ facilities
- Flat-screen TV
- Laundry
- Tea and coffee facilities
- Pool with view
- Outdoor swimming pool
Ma178 Green Pineapple
Staying at Ma178 Green Pineapple Marathon villa, guests can visit Conch-Air Florida Keys Scenic Flights, which is nearly a 25-minute walk away. Guests can enjoy cycling and fishing at the Marathon holiday home, located only 1.3 km from the San Pablo Catholic Church.
Carney'S Reef New 1B 1B Pool Patio
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Ironing facilities
- Golf centre
- Outdoor swimming pool
Staying at the 1-bedroom Carney'S Reef New 1B 1B Pool Patio Villa Marathon, guests can easily reach Conch-Air Florida Keys Scenic Flights, located merely 1.9 km away. Guests can enjoy cycling and fishing at this Marathon holiday home, located within 15 minutes' walk of 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
Staying at the 1-bedroom Carney'S Reef New 1B 1B Pool Patio Villa Marathon, guests can easily reach Conch-Air Florida Keys Scenic Flights, located merely 1.9 km away. Guests can enjoy cycling and fishing at this Marathon holiday home, located within 15 minutes' walk of 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 the Bayview Park, the spacious Kw23 Atlantic Ocean View Apartment Key West is 3.1 km from a top family-friendly place like the Key West Aquarium. Wi-Fi is available 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 the Bayview Park, the spacious Kw23 Atlantic Ocean View Apartment Key West is 3.1 km from a top family-friendly place like the Key West Aquarium. Wi-Fi is available 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.