
Vacation rentals with a pool in Middletown
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Middletown
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Secluded Oasis w/ Heated Salt Pool - 10 to Newport
Welcome to your Newport escape—an elegant, sun-filled retreat designed for elevated coastal living: • Heated saltwater pool (late May–Sept) set within our lush, manicured grounds • Beautiful, updated interiors with timeless finishes and thoughtful design • Minutes to 1st & 2nd Beach, Newport Harbor, boutiques, and dining • High-end kitchen ideal for entertaining • Outdoor veranda + deck for alfresco lounging, grilling, and gatherings • Three fireplaces (seasonal) + bonus spaces with games

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. Quite, tranquil, relax. As of 1/1/26 booking rate will be $120 per day. Pool $20 seasonal.

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.

Entire House & HotTub. Bring your Dog!
Get ready to soak up the sun and enjoy some fun at this Somerset vacation rental! This family and PET-friendly house features 5 bedrooms, 2 bathrooms, and a beautiful backyard you won't want to leave! Near the Rhode Island Border!! Fire up the grill and enjoy dinner al fresco before gathering around the fire pit or relaxing in the hot tub. The spacious kitchen has everything you need to prepare meals before a day of exploring Pierce Beach, hiking in Colt State Park, or Lizzie Borden history!

Bass Rocks Upper Decks, special winter rates
With 10+ years of STR history with a 5 star rating, Bass Rocks Upper Deck is new to Airbnb. This spacious loft is located in a large historic carriage house that was remodeled into 3 apartments with privacy in mind. 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.

Oyster Hill
Fall in love with the Ocean State from this gorgeous 4-bedroom, 3-bath vacation home. Situated close to all that Aquidneck Island is known for — Steps from the Glen Manor Mansion, walking distance to Newport Polo, 15 minutes to downtown Newport, the Cliff Walk, and numerous beaches — this home away from home is ideal for who love life by the sea. After exploring, curl up with a good book in the sitting room or work remotely from the home office. Most rooms come with sparkling ocean views!

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.

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:Coastal Cottage in town near beach/Nwp
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.

2BR Newport Onshore Condo on Lovely Resort
Considered by many as the “Yachting Capital of the World,” Newport is New England's proud city-by-the-sea. The Newport Onshore Resort is situated right on the shores of the Newport Harbor, on Thames Street in the Newport city center. Guests are walking distance to the best museums, antique shops, restaurants, and art galleries. The harbor and marina are the perfect spot to watch beautiful boats gently float past or charter a sailboat for the day.
Popular amenities for Middletown rentals with a pool
House rentals with a pool

Hopeworth Homestead. Sleeps 10+ Pool, Beach, AC

Private Heated Pool • Upscale 4BR • 13 min 2 Beach

Cozy Coastal Escape in Warren | Dog Friendly

Pier Escape

Minimal Modern Home Getaway

Charlestown RI Oasis !

Mid-Cent Artist Cape, Pool, 3B, Beaches, 22 Acres

Beach House in the Pier W/ POOL. Book for 2026!
Condo rentals with a pool

August Newport Inn on Long Wharf, Waterfront Unit

Newport Oceanfront Resorts

Wyndham Long Wharf Resort |2BR King Suite

Timeshare Rental. 3rd floor Condo w/ water view

Newport Resorts

Wyndham Newport Overlook | 2BR/2BA King Bed Suite

1BR Condo w/ Bay Views + Jacuzzi Tub

Wyndham Newport Onshore|1BR/1BA Balcony King Suite
Other vacation rentals with a pool

Beachhouse with Pool, Treehouse + 3 Seasons Room

River Front Farm Style Living

Beautiful historic house in the heart of Bristol

Family-Friendly Beach Getaway

Private suite-2 bed/2 bath, pool/ hot tub access

WFH Friendly: Cozy Winter Retreat in Bristol!

Downtown Waterfront Resort

private coastal getaway
When is the best time to visit Middletown?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ474 | ﺩ.ﺇ547 | ﺩ.ﺇ577 | ﺩ.ﺇ716 | ﺩ.ﺇ826 | ﺩ.ﺇ1,186 | ﺩ.ﺇ1,601 | ﺩ.ﺇ1,711 | ﺩ.ﺇ1,678 | ﺩ.ﺇ757 | ﺩ.ﺇ474 | ﺩ.ﺇ474 |
| Avg. temp | -2°C | -1°C | 3°C | 8°C | 13°C | 18°C | 22°C | 21°C | 17°C | 11°C | 6°C | 1°C |
Quick stats about vacation rentals with a pool in Middletown

Total vacation rentals
Explore 410 vacation rentals in Middletown

Nightly prices starting at
Middletown vacation rentals start at ﺩ.ﺇ220 per night before taxes and fees

Verified guest reviews
Over 4,830 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
250 properties have a dedicated workspace

Wi-Fi availability
410 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
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- Foxwoods Resort Casino
- Brown University
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