
Holiday 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.

Beachfront W/ HotTub, Sauna, Pool & Panoramic view
Welcome to the Heart of Somerset! Nestled at the very tip of Somerset on a private dead-end road, this coastal waterfront home is the perfect place for a family retreat, romantic getaway or friends seeking adventure Marvel at the panoramic views and dramatic colors from Sunrise to Sunset of the Braga Bridge, Mt. Hope Bridge & Bay, Bristol, Tiverton Rhode Island & the Fall River cityscape on the horizon. Grab a kayak or relax, soak up the sun & let the gentle sea breeze wash your worries away!

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.

Campfires & Porch Swings, 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.

Waterfront Oasis Pool EPIC Views
Welcome to Sakonnet Sunset Manor! This stunning 4BR/2BA home sleeps 6 - 8 guests and offers epic waterfront views. Featuring 40ft pool w/hot tub, three king-size beds, 2-in-1 trundle bed, laundry, & indoor and outdoor dining areas. Relax on the front and rear porches allowing the stress to melt away as you Savor breathtaking west-facing sunsets over the Sakonnet River! Just 0.4 mi from Grinnell's Beach, near Evelyn's Diner, Bridgeport Seafood, Coastal Roasters, Red Dory & Black Goose Cafe.

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.

Modern Home w/ Pool & Game Room | Mins to Newport
Here’s a tightened, natural version under 500 characters with the game room woven in smoothly. Escape to our upscale 5 bedroom home in Middletown, RI, just minutes from the beach and downtown Newport. Sleeps 10 comfortably and is perfect for weddings or group getaways. Enjoy the private pool, fire up the grill, challenge friends in the game room, or relax with a movie night. A prime location, plenty of space, and amenities designed for memorable stays year after year.

Jamestown: Cottage New Year’s 1 night Min. Grab it
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.

Vineyards, Newport, Narragansett, In-Ground Pool
Wickford area of North Kingstown , 5 minutes to Gooseneck Vineyards. Clean, Smoke Free Home w/room to spare! Large 4 bed/3 bath with pool and cabana, central a/c, 15 minutes from Narragansett, Newport. 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!
Popular amenities for Middletown rentals with a pool
House rentals with a pool

HUGE family house. 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!
Apartment rentals with a pool

Wyndham Onshore 2 Bedroom

August Newport Inn on Long Wharf, Waterfront Unit

Newport Oceanfront Resorts

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

Wyndham Long Wharf Resort |2BR King Suite

Timeshare Rental. 3rd floor Condo w/ water view

Newport Resorts

Ocean Front View! Wyndham Inn on Long Wharf Resort
Other holiday rentals with a pool

Beachhouse with Pool, Treehouse + 3 Seasons Room

River Front Farm Style Living

Modern Tiny Home | Stunning Views + Top Amenities

Serenity Retreat

Beautiful 2-story Apartment in Oceancliff

Cozy 2BR Long Wharf Resort

Timeshare overlooking Narragansett Bay

Family-Friendly Beach Getaway
When is the best time to visit Middletown?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $165 SGD | $191 SGD | $201 SGD | $250 SGD | $289 SGD | $414 SGD | $559 SGD | $598 SGD | $586 SGD | $382 SGD | $246 SGD | $183 SGD |
| 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 holiday rentals with a pool in Middletown

Total holiday rentals
Explore 400 holiday rentals in Middletown

Nightly prices starting at
Middletown holiday rentals start at $103 SGD per night before taxes and fees

Verified guest reviews
Over 4,520 verified reviews to help you choose

Family-friendly holiday rentals
220 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
240 properties have a dedicated workspace

Wifi availability
400 of Middletown holiday rentals include wifi 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
- Charlestown Beach
- East Sandwich Beach
- Craigville Beach
- Point Judith Country Club
- Duxbury Beach
- Ocean Beach Park
- Easton Beach
- Blue Shutters Beach
- Onset Beach
- Groton Long Point Main Beach
- Oakland Beach
- White Horse Beach
- Horseneck Beach State Reservation
- Roger Williams Park Zoo
- Second Beach
- The Breakers
- Pinehills Golf Club
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- Island Park Beach
- Groton Long Point South Beach
- South Shore Beach
- Goddard Memorial State Park




