Search Vacation Homes in Sugarloaf Key
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check prices for these dates
Next weekend
In two weeks
In one month
In two months
Our top choices for Sugarloaf Key vacation homes
Vacation Home in Summerland Key
Starlight Serenity - Hideaway w Stunning ViewsThe price is AED 967
AED 2,316 total
includes taxes & fees
11 Dec - 12 Dec
Vacation Home in Summerland Key
Starlight Serenity - Hideaway with Stunning ViewsThe price is AED 690
AED 2,144 total
includes taxes & fees
11 Dec - 12 Dec
Vacation Home in Upper Sugarloaf Key
The Hemingway - Beach Houses Key West9.8 out of 10, Exceptional, (7)
"Perfect location way off the path if you like seclusion."
Jonathan L.
The price is AED 5,050
AED 8,388 total
includes taxes & fees
3 Jan - 4 January 2026
Vacation Home in Upper Sugarloaf Key
The Lighthouse - Beach Houses Key West9.6 out of 10, Exceptional, (11)
"Thank you for our wonderful stay at this beautiful property - everything was perfect - Peter"
Peter Q.
Vacation Home in Sugarloaf Key
Azucar - Beach Houses Key West10.0 out of 10, Exceptional, (10)
"The location of the home is great, beautiful and peaceful.Enjoyed the pool."
Rachel N.
Vacation Home in Sugarloaf Key
Hammock House - Beach Houses Key West8.0 out of 10, Very Good, (2)
"If you're looking for a peaceful and picturesque getaway, the Bungalows at Sugarloaf Beach is the perfect choice!Thank you, Cadmier, for your hospitality. See again. Respectfully, Samat Sakebaev "
Samat S.
The price is AED 8,060
AED 12,525 total
includes taxes & fees
27 Dec - 28 Dec
Vacation Home in Upper Sugarloaf Key
Palm - Beach Houses Key West10.0 out of 10, Exceptional, (14)
"Beautiful grounds and pool area. Enjoyed all the abundant wildlife as well as fishing from one of the piers."
Harvey(Tabb) M.
The price is AED 3,212
AED 6,265 total
includes taxes & fees
11 Dec - 12 Dec
Vacation Home in Cudjoe Key
DECEMBER SAVE 60% OFF! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS9.4 out of 10, Exceptional, (101)
"Great location. "
Davian k.
The price is AED 547
AED 1,594 total
includes taxes & fees
14 Dec - 15 Dec
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.
Top Sugarloaf Key Hotel Reviews
Winslow's Bungalows - Key West Historic Inns
10/10 Excellent
Explore a world of travel with Expedia
Popular Destinations
More Accommodation Types in Sugarloaf Key
- Condo Rentals in Sugarloaf Key
- Apartments in Sugarloaf Key
- Cottages in Sugarloaf Key
- Guest Houses in Sugarloaf Key
- Houseboats in Sugarloaf Key
- Resorts in Sugarloaf Key
- Villas in Sugarloaf Key
- B&B in Sugarloaf Key
- Aparthotels in Sugarloaf Key
- RV Parks in Sugarloaf Key
- Cabin Rentals in Sugarloaf Key
- Motels in Sugarloaf Key
- Hostels in Sugarloaf Key
- Inns in Sugarloaf Key
- Hotels