
Vacation rentals with a pool in Middletown
Find and book unique homes with a pool on Airbnb
Quick stats about vacation rentals with a pool in Middletown

Total vacation rentals
Explore 480 vacation rentals in Middletown

Nightly prices starting at
Middletown vacation rentals start at $80 per night before taxes and fees

Verified guest reviews
Over 5,480 verified reviews to help you choose

Family-friendly vacation rentals
270 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 80 rentals that welcome pets

Rentals with dedicated workspaces
280 properties have a dedicated workspace

Wi-Fi availability
480 of Middletown vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Middletown rentals

4.7 Average rating
Middletown stays receive an average rating of 4.7 out of 5 from guests
Top-rated rentals with a pool in Middletown
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Boutique Luxury Waterfront w/Pool & Sunset Views
Experience unforgettable sunsets at Sakonnet Sunset Manor. This luxury boutique waterfront escape sleeps 6 in a private 2.5BR/1BA unit, offering panoramic views of Sakonnet River. Relax w/private access to the 40-ft pool & hot tub (Apr–Oct) enjoy outdoor dining on spacious rear deck, or unwind w/ coffee or cocktails on the charming front porch in six cushioned recliners. Snuggle into Two king beds, 2-in-1 trundle, cozy fireplaces after a day at Grinnell's beach. Search YT for walkthrough video.

Close to Town, Beach & Vineyards! Pool!
Welcome to your ideal coastal retreat. This spacious 4-bedroom, 2-bath home comfortably sleeps up to 8 guests and blends modern amenities with an unbeatable location. Just minutes from wineries and local beaches, the home is perfect for relaxing and recharging. Enjoy a gated backyard featuring a private pool (open mid-Jun through mid-Sept), fire pit, and a beautiful deck with BBQ grill. Inside, you’ll find a well-equipped kitchen and generous living spaces designed for comfort and connection.

Stunning Farmhouse - Private Pool & Vintage Arcade
Escape to your perfect Coastal Country Retreat: Luxury Farmhouse with Pool and Vintage Arcade! This spacious 3+ bedroom, 4-bath home can accommodate up to 6 overnight Adult guests and up to 4 children 12 or under for a total of 10 guests. These limits are governed by the Middletown ordinances and they must be adhered to. Please read our full descriptions and house rules before requesting a booking to make sure the home is a great fit for your stay !! We look forward to hosting you!

Dwntwn 1BR/Pool/Gym/Parking/Hi-Speed WiFi/King Bed
Just steps away from everything that downtown Providence has to offer is our beautifully furnished upscale apartment with a view of the city & courtyard. This space offers a large fully equipped kitchen, king size bed, high speed internet, 55" smart TV w/Disney+ & Netflix. The building has a fitness center, heated lap pool, BBQ & picnic area, a concierge, resident lounge & covered parking. No car needed, we are just a short walk to all shops, restaurants, the mall & amazing Waterfire!

Private POOL, Central AC, Walk to beach, king MBR
Summer 2025/2026 full weeks run SUNDAY to SUNDAY. Max capacity: 8 adults, 4 kids under 12. Spacious 4-5BD/2BA, close to downtown Newport, walk to beach, fully fenced private backyard and OWN POOL. Newly remodeled KITCHEN. King bed master BD. Great family neighborhood. Good fit for families, weddings/reunions, kids. CENTRAL AIR. Easy secure check in with private 4 digit code; No keys to lose! Minutes walk to the Atlantic Resort. Walk to Newport's best beaches and many restaurants.

Bass Rocks Carriage House apartment
Bass Rocks Carriage House is located in a large Gilded Age carriage barn that was remodeled for 3 separate apartments with privacy in mind. This unit combines the best of antique details and modern amenities. Just 5 minutes' drive to downtown Newport and a short walk to Sachuest (Second) Beach, it has one of the best locations in the Northeast! The beautiful mile of public beach only 1500 feet away is the best in town for sun bathing, swimming, or surfing at legendary Surfer's End.

Get comfy in the country!
This special place is close to everything, making it easy to plan your visit. Just 10 minutes away from town. Secluded cabin on a 57-acre farm outlooking a large paddock with 4 highland cows. This beautiful property has a neighboring golf course and trails connecting to Heritage Park. Pool. Fireplace. Amazing sunsets! Who wouldn’t want to live like Yellowstone for a little? Home of Welcome Pastures, a Nonprofit 501(c)3 organization. Portion of proceeds go towards the foundation.

Jamestown: In town cottage near Newport 9/2-5 OPEN
The cottage is a perfect getaway in the Ocean State. It is an ideal location within walking distance of restaurants, shops, local beaches & parks. The renovated chef's kitchen is an entertainer's delight. This 3/2 home has two living rooms and high-speed internet allowing for ample work and play. The private outdoor deck features a hot tub (open during the winter), pool, fire pit, BBQ, gazebo, multiple seating areas, and a backyard for additional recreational space.

Artist studio in the woods
Take it easy at this unique and tranquil getaway. Be a little bohemian, stay in an artist’s studio for two adults, views of woods and stone walls.walk along a 300 stone wall past a 5000 gallon koi pond, and discover a stone sculpture in the woods. Wall of windows, private deck, queen size bed, kitchenette, full bath, dishwasher, Wi-Fi, cable tv, guest robes, iron and board, kuerig, all necessary utensils. Quiet, tranquil, relax. 47 minutes from Gillette Stadium.

Private Heated Pool • Upscale 4BR • 13 min 2 Beach
Enjoy a private heated salt-water pool, spacious living areas, and dining for ten — perfect for families and groups looking for comfort, privacy, and easy access to beaches, mansions, and downtown Newport. Relax in your own private oasis just minutes from Newport. Welcome to #ChiquitaCasita, a thoughtfully designed 4-bedroom home offering the space, comfort, and amenities guests want — without the congestion or parking challenges of downtown Newport.

Vineyards, Newport, Narragansett, In-Ground Pool
Close to Newport, Narragansett and the quaint Wickford Village, minutes to Gooseneck Vineyards. Clean, Smoke Free Home w/room to spare! Large 4 bed/3 bath with pool and cabana, central a/c. Short 5 minute ride to NK town beach. If you're not in the mood for the beach, relax in the in-ground pool. (Seasonal May-Sept)10 minutes from TF Green airport and Wickford Train station, 10 minutes to University of Rhode Island. In the middle of EVERYTHING!

Newport 3BR Long Wharf Waterfront Resort
The Long Wharf Resort managed by Wyndham is located on the picturesque waterfront bordering downtown Newport. Venture out from your suite and explore the vibrant Thames Street where you'll discover a wealth of coffee shops, antique stores, art galleries and live music entertainment. A variety of Newport attractions and things to do are within walking distance from this premier waterfront vacation resort in the heart of beautiful Newport.
Popular amenities for Middletown rentals with a pool
House rentals with a pool

Oyster Hill

Cozy Coastal Escape in Warren | Dog Friendly

Vitamin Sea Pier Beach House POOL. Book Fall 2026!

Minimal Modern Home Getaway

Family-Friendly Beach Getaway

Barrington Oasis: Waterview with an Inground Pool!

Three bedroom home with pool, dogs considered

Waterfront Historic Wickford Village Home!
Condo rentals with a pool

Wyndham Long Wharf | 3BR/2BA King Bed Suite

Wyndham Long Wharf Resort |2BR King Suite

1 Bedroom at Club Wyndham Inn on The Long Wharf

Timeshare Rental. 3rd floor Condo w/ water view

Wyndham Inn on Long Wharf |1BR/1BA King Bed Suite

Seaside Escape – Marina, Dining & Fun

Cozy Newport 1BR/1BA Retreat Steps from the Wharf

Wyndham Inn on Long Wharf |1BR/1BA King Bed Suite
Other vacation rentals with a pool

The Denison Markham Carriage House

Mali's Place

Wyndham Long Wharf Resort near Fisherman's Wharf

★2 BEDROOM SUITE★ Wyndham Newport Onshore Resort!

Modern, Bright, Private Studio w/POOL

Newport Waterfront 1 Bedroom

NEW ENGLAND SEAPORT ESCAPE in our 2 Bedroom Deluxe

In the heart of Newport
When is the best time to visit Middletown?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $125 | $133 | $146 | $218 | $307 | $409 | $436 | $466 | $457 | $206 | $129 | $129 |
| Avg. temp | 29°F | 30°F | 37°F | 46°F | 56°F | 65°F | 71°F | 69°F | 63°F | 52°F | 42°F | 34°F |
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