Jamaica Summer Rentals, Cottages & Cabins

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

• Entire apt 2 BR Sunnyside -30 day minimum stay*
• Celebrity Retreat | Heated Pool, Gym, STEAM Spa
• Modern 2BR Near LaGuardia & Subways
• Cozy Studio Near Rockaway Beach Come enjoy the ocean as desired !
• Modern vacation rental w/hot tub. 15 minutes from the airport
• Comfy 2B Near LGA & Subway with Washer/Dryer
• RITCHSON LOFTnTree House in NYC!
• Cozy, Luxury 1-2 Bedroom Townhome by Main Street in Charming Flushing, NY.
• Stylish Studio Apartment on Main Street with Courtyard and Free Parking!
• 10 minutes to Manhattan! Cozy 2 bedroom in LIC/Astoria, in the center of it all.

In 2026, Topwintervacations offers 320 summer rentals in or around Jamaica. 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 Jamaica is $578. Check the full list of summer accommodations in Jamaica.

There are 320 summer rentals, cabins, cottages and properties that are available to rent. Book for your next trip with Topwintervacations.

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

• Beach Front,Ideal for family and couples,beautiful place for sunset lovers!
• Adorable 1 bedroom cottage
• Home2 Suites by Hilton NY Long Island City/Manhattan View
• "Seaside Nest" - Rockaway Beach, NY - On Beach Block

Check all holiday rentals with a pool in Jamaica on Topwintervacations.