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
In two weeks
In two months
In three months
In four months
Our top choices for Sugarloaf Key vacation homes
Private and Exclusive Florida Keys Getaway
Private and Exclusive Florida Keys GetawayUpper Sugarloaf Key
10.0 out of 10, Exceptional, (14 reviews)
"Beautiful! Pool was amazing!"
Jennifer B.
The price is AED 2,121
AED 4,349 total
includes taxes & fees
26 May - 27 May
The Lighthouse - Beach Houses Key West
The Lighthouse - Beach Houses Key WestUpper Sugarloaf Key
9.6 out of 10, Exceptional, (11 reviews)
"Thank you for our wonderful stay at this beautiful property - everything was perfect - Peter"
Peter Q.
The price is AED 2,808
AED 5,417 total
includes taxes & fees
18 May - 19 May
Starlight Serenity - Hideaway with Stunning Views
Starlight Serenity - Hideaway with Stunning ViewsSummerland Key
10.0 out of 10, Exceptional, (1 review)
"This place was everything we needed. The location was the perfect combination of secluded but with accessibility to Marathon and Key West. The house had everything we needed. We loved the appliances, the bed, the shower and the wrap-around porch with the swing. And the people managing the property made our visit the best experience from booking to departure. Will book again!"
Tom H.
The price is AED 1,249
AED 2,806 total
includes taxes & fees
24 May - 25 May
The Hemingway - Beach Houses Key West
The Hemingway - Beach Houses Key WestUpper Sugarloaf Key
9.6 out of 10, Exceptional, (8 reviews)
"Great place for our family of 5 A little off the beaten path which is exactly what we wanted Great host who answered all our questions promptly Sunrise and sunsets here were magnificent Great fishing off the dock as well"
Brian K.
The price is AED 3,374
AED 6,264 total
includes taxes & fees
2 Jun - 3 Jun
Starlight Serenity - Hideaway w Stunning Views
Starlight Serenity - Hideaway w Stunning ViewsSummerland Key
The price is AED 1,917
AED 3,497 total
includes taxes & fees
24 May - 25 May
Private and Exclusive Beach Getaway
Private and Exclusive Beach GetawaySugarloaf Key
10.0 out of 10, Exceptional, (11 reviews)
"The location of the home is great, beautiful and peaceful.Enjoyed the pool."
Rachel N.
Private and Exclusive Beach Getaway
Private and Exclusive Beach GetawaySugarloaf Key
8.0 out of 10, Very Good, (2 reviews)
"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 5,232
AED 9,168 total
includes taxes & fees
17 May - 18 May
Bright 2BR 2BA in Cudjoe Key| Sleeps 6 | WiFi | Washer Dryer | Near Water & Key West
Bright 2BR 2BA in Cudjoe Key| Sleeps 6 | WiFi | Washer Dryer | Near Water & Key WestCudjoe Key
The price is AED 868
AED 2,350 total
includes taxes & fees
14 May - 15 May
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.
Find vacation rentals that suit your style
Houseboats
Private vacation homes
Save an average of 15% on thousands of hotels when you're signed in
Top Sugarloaf Key Hotel Reviews
Blue Flamingo Resort Key West
10/10 Excellent
Explore a world of travel with Expedia
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
- B&B in Sugarloaf Key
- Villas in Sugarloaf Key
- Aparthotels in Sugarloaf Key
- RV Parks in Sugarloaf Key
- Motels in Sugarloaf Key
- Cabin Rentals in Sugarloaf Key
- Hostels in Sugarloaf Key
- Inns in Sugarloaf Key
- Hotels