Sugarloaf Key Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks

Our top choices for Sugarloaf Key vacation rentals

Vacation Home in Summerland Key

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
The price is P23,760
P46,386 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Starlight Serenity - Hideaway w Stunning Views

Houseboat in Stock Island

Aqua Lodges at Hurricane Hole Marina
2.0 star property
8.8 out of 10, Excellent, (170)
"Location , staff , and aqua lodge were perfect."
United States
William
The price is P12,108
P23,469 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Aqua Lodges at Hurricane Hole Marina

Mobile Home in Big Pine Key

Sunshine Key RV Resort & Marina
2.0 star property
8.8 out of 10, Excellent, (160)
"Staff was great. Room so clean! Loved the shower. Bed comfy and the property was beautiful! "
United States
brenda
The price is P17,918
P20,158 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Sunshine Key RV Resort & Marina
2.5 star property
8.6 out of 10, Excellent, (283)
"Enjoyed the duplex, instead of a standard hotel room. Full kitchen, nice bathroom, and bedroom. "
United States
Alejandra
Old Wooden Bridge Resort and Marina
2.0 star property
10.0 out of 10, Exceptional, (1)
The Grenada Suite Pool View Private Balcony
3.5 star property
10.0 out of 10, Exceptional, (1)
"We were here for a night and it was great. A nice rustic feel on a big property, with good view. "
United States
Preetam
The price is P33,090
P60,390 total
includes taxes & fees
Jan 16 - Jan 17, 2026
Atlantic View Luxury Villa with Pool

Vacation Home in Old Town Key West

Contra House Key West
3.0 star property
The price is P67,592
P99,572 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Contra House Key West
3.0 star property
The price is P58,107
P77,119 total
includes taxes & fees
Jan 10 - Jan 11, 2026
Coconut Mallory Marina and Resort Condo
2.0 star property
10.0 out of 10, Exceptional, (3)
"Nice place "
United States
Pawel
The price is P37,965
P56,986 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Grand Marina Suite by Brightwild Waterfront

Apartment in Key West Historic District

Mesa House Uno by Brightwild Perfect Location
2.0 star property
The price is P39,891
P55,583 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Mesa House Uno by Brightwild Perfect Location

Apartment in Key West Historic District

The Bartlum Luxury Studio In Prime Location
2.0 star property
The price is P34,182
P49,162 total
includes taxes & fees
Jan 11 - Jan 12, 2026
The Bartlum Luxury Studio In Prime Location

Aparthotel in Key West

Ocean Front One Bedroom Residence
2.0 star property
The price is P36,295
P45,835 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Ocean Front One Bedroom Residence

Apartment in Key West Historic District

New Coastal Rose - Bright Loft With High Ceilings
2.0 star property
The price is P41,322
P64,356 total
includes taxes & fees
Jan 11 - Jan 12, 2026
New Coastal Rose - Bright Loft With High Ceilings
2.0 star property
10.0 out of 10, Exceptional, (1)
"Our family spent one night at Key West and we fully enjoyed our stay here. Room is very clean, stylish and spacious. Beds are comfortable."
United States
Xiulin
The Trinidad by Brightwild Pool View Parking

Apartment in Key West Historic District

Banana Split by Brightwild Pool Grill
2.0 star property
Banana Split by Brightwild Pool Grill

Apartment in Key West Historic District

New The Cottage at James House
2.0 star property
8.0 out of 10, Very Good, (2)
"The best thing about this property is location. Short walk to everything - short walk to Sloppy Joes. It is overpriced for the accommodations but you pay for location. "
United States
Pamela
The price is P33,678
P45,035 total
includes taxes & fees
Jan 20 - Jan 21, 2026
New The Cottage at James House

Apartment in Old Town Key West

Poolside Suite by Brightwild Pvt Pool Parking
2.0 star property
The price is P31,680
P51,722 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Poolside Suite by Brightwild Pvt Pool Parking

Apartment in Old Town Key West

Sea Breeze by Brightwild Off-street Parking
2.0 star property
The price is P47,181
P71,994 total
includes taxes & fees
Jan 10 - Jan 11, 2026
Sea Breeze by Brightwild Off-street Parking

Apartment in Old Town Key West

Duval Dream Loft by Brightwild Right on Duval
2.0 star property
10.0 out of 10, Exceptional, (1)
Duval Dream Loft by Brightwild Right on Duval

Vacation Home in Old Town Key West

Contra House by Brightwild Luxury Home w Pool
2.0 star property
Contra House by Brightwild Luxury Home w Pool
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Top Sugarloaf Key Hotel Reviews

Find out more about Sugarloaf Key

Search for holiday rentals in Sugarloaf Key on Expedia! You can easily find your home rentals, villas, holiday apartments in Sugarloaf Key using one of the methods below:

  • View our selection of featured holiday rentals in Sugarloaf Key
  • Use the map to find apartments and other holiday homes in the Sugarloaf Key neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Sugarloaf Key while they last

Look no further and take a look at our great range of rental properties in Sugarloaf Key!