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Key West Summer Rentals, Cottages & Cabins

Book a Place to Stay in Key West for Your Summer Getaway

About Key West Summer Rental on PickleTrip

PickleTrip™'s summer rentals in Key West are perfect for your next summer getaway. We offer a wide range of properties to choose from, including homes with top-notch pickleball courts or nearby facilities, private pools, indoor/outdoor pools, hot tubs, WiFi, beach access, and more. Whether you're traveling with family, friends, or a group, we have a rental that will suit your needs.

Enjoy the perfect summer vacation in Key West with PickleTrip™. Our summer rental homes are designed to provide you with maximum comfort and relaxation. Choose from a variety of properties, including condos, resorts, villas, bungalows, cozy cabins, RVs, and cottages. Stay and play pickleball when you travel with PickleTrip™.

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Frequently Asked Questions About Key West Luxury Rentals

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

In 2025, PickleTrip offers 4633 summer rentals in or around Key West. 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 Key West is $786. Check the full list of summer accommodations in Key West.
There are 4633 summer rentals, cabins, cottages and properties that are available to rent. Book for your next trip with PickleTrip.

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

Check all holiday rentals with a pool in Key West on PickleTrip.

Yes, We have 4633 summer rental homes in Key West and types of place to stay in Key West include:

  • Vacation Homes: 4633 available for rent
  • Villas: 4633 Rentals available for rent
  • Holiday Apartments: 4633 Rentals available for rent
  • Hotels with Suites: 4633 Rentals available for book
Yes, of course! There are many luxury summer rental properties in Key West. 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 Key West.