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Upper Harbor Key Summer Rentals, Cottages & Cabins

Book a Place to Stay in Upper Harbor Key for Your Summer Getaway

About Upper Harbor Key Summer Rental on StayAndPlay

Looking for the perfect summer golf trip in Upper Harbor Key? StayAndPlay offers a unique collection of golf villa rentals, including golf cabins, golf resorts, golf retreats, and more. Our properties are equipped with luxurious amenities such as private decks, swimming pools, hot tubs, Wi-Fi, and stunning golf course views. Whether you’re traveling with family, friends, or a larger group, our golf accommodations in Upper Harbor Key provide the ideal setting for an unforgettable golf vacation.

Make the most of your summer golf retreat in Upper Harbor Key with StayAndPlay. Our selection of golf accommodations ensures maximum comfort and relaxation. From elegant golf villas to private golf retreats and cozy golf cabins, each home offers a one-of-a-kind experience on the course. Find your perfect golf villa for the ultimate summer retreat in Upper Harbor Key with StayAndPlay. Ready to make your best swing? Book your dream golf escape with StayAndPlay!

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Summer Rental: Explore Top Destinations

Frequently Asked Questions About Upper Harbor Key Luxury Rentals

There are a lot of options in Upper Harbor Key. If you plan on staying in the Upper Harbor Key area, consider making a reservation for a few nights at one of these properties as these have been rated the top Summer Rentals in Upper Harbor Key:

In 2026, StayAndPlay.com offers 1148 summer rentals in or around Upper Harbor Key. Find unique home rentals for your summer holiday or a weekend getaway with family and friends.
The average price per night for a summer rental in Upper Harbor Key is $424. Check the full list of summer accommodations in Upper Harbor Key.
There are 1148 summer rentals, cabins, cottages and properties that are available to rent. Book for your next trip with StayAndPlay.

Yes, here are some popular summer holiday rentals in Upper Harbor Key that have a private or indoor pool:

Check all holiday rentals with a pool in Upper Harbor Key on StayAndPlay.

Yes, We have 1148 summer rental homes in Upper Harbor Key and types of place to stay in Upper Harbor Key include:

  • Vacation Homes: 1148 available for rent
  • Villas: 1148 Rentals available for rent
  • Holiday Apartments: 1148 Rentals available for rent
  • Hotels with Suites: 1148 Rentals available for book
Yes, of course! There are many luxury summer rental properties in Upper Harbor Key. Use our search filter to discover all of our luxury summer accommodations with an indoor/outdoor pool. Sorting by price is another way to find the most and least expensive luxury summer rentals in Upper Harbor Key.