Vacation rentals near Upper Sugarloaf Key
We found 655 vacation rentals — enter your dates for availability
Discover a selection of private vacation rentals close to Upper Sugarloaf Key that are perfect for your trip. Whether you're traveling with a group or just with your pet, vacation rentals have the best amenities for hanging out with the people that matter most, including WiFi and parking. You'll be sure to find a rental to meet everyone's needs, including places that are non-smoking or accessible.
Vacation rentals with weekly discounts - Upper Sugarloaf Key
Showing deals for:Nov 14 - Nov 21
Image gallery for A Tropical Luxury Getaway, Your own private resort!!
10 out of 10 rating
Exceptional
(38 reviews)
A Tropical Luxury Getaway, Your own private resort!!
Summerland Key, FL
10% off
Price is CA $3,220
CA $28,157 total
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Find the best place to stay - Upper Sugarloaf Key
Oasis - Ocean front with pool
Sleeps 12 · 4 bedrooms · 4 bathrooms
9.0 out of 10
wonderful
(28 reviews)
Top rated rentals - Upper Sugarloaf Key
Wonderful Stay!
10 out of 10
exceptional
(49 reviews)
Can’t wait to return! I have to say that initially I was a little apprehensive when I read that the owners may be present during our stay, but very quickly my apprehensions were lifted as we rarely saw Nancy and Bob. When we did have a chance to have a quick visit, they were lovely, gracious hosts. The property is well-maintained, and it is a beautiful location. We thoroughly enjoyed ourselves! Thank you Nancy and Bob!
-Kim, Mitch and Cindy
Kim A.
Stayed Mar 2024
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, yards and more
More for lessMore space, more privacy, more amenities — more value