Looking for a specific home?
Dream Island Views of Orient Bay - 4 Suites / Sleeps 8
Ski-in/Ski-out 1 Bdrm 1 Bath Slopeside Chalet - Sleeps 2
Best Luxury 4 Bedroom+Den & Walk to Slopes! Sleeps 12+
NEW 3 Bdrm w/ Pool and Views for Days!
Sweetgrass Ranch
Villa Casa Sunshine - 10 Suites
Sky Walker Ranch
2 Bed 2.5 Bath Cupecoy Penthouse with Marina Views
SKY is your premier vacation rental company offering a variety of private properties for rent, including the finest luxury villas, condominiums, ranches, town-homes, and rustic cabins for rent. From a 10 bedroom luxury ocean-front beach estate, to economical island condominiums, to luxury ranches out west, to beautiful lodges in ski country, SKY can find you a property that fits your needs. SKY is currently offering private vacation villas and condos for rent on Sint Maarten Island - Saint Martin Island, exquisite ranches in Montana, luxurious homes in the heart of Vail, and rustic cabins in Wisconsin, all complemented with a wide range of concierge services.  

Several of our properties are featured in some of the most prestigious architectural magazines and are among the most exclusive homes in their respective destination, for their design, location, personality and features. Our experience has shown that those who have had a proper "private rental experience" cease to even consider going to a hotel for their vacation.  

Each of our properties are hand picked and personally inspected by the SKY staff.  When you rent from SKY, you can be assured of the quality, location, and amenities illustrated on our site are accurate.

Please contact us as we are happy to discuss which property is best suited for your next vacation!