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 €69 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.

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Top guest favorite
The serene outdoor pool area features a spacious heated pool and spa, surrounded by a gray stone patio. Numerous lounge chairs are evenly arranged around the pool, with green trees providing a natural backdrop. A gated fence surrounds the area, enhancing security and privacy.
Apartment in Tiverton
4.96 out of 5 average rating, 57 reviews

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.

Guest favorite
A single-story home is set back from the street, featuring light blue siding and white trim. A well-maintained lawn surrounds the house, with a variety of shrubs and ornamental plants. A small path leads to the front steps, enhancing the inviting entrance.
Home in Middletown
4.98 out of 5 average rating, 43 reviews

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.

Superhost
An aerial view of a spacious vacation home features a large, inviting outdoor swimming pool surrounded by landscaped greenery. The home's exterior showcases a combination of wood and shingle siding, with multiple gabled roofs and well-maintained gardens. Seating areas are visible near the pool.
Home in Middletown
4.86 out of 5 average rating, 7 reviews

Solo Fish - Family home, walk to beach and pool!

STAY proudly presents "Solo Fish." 4-bed, 4-bath + POOL vacation home centrally located to all. Our home features an outdoor swimming pool with bar, perfect for entertaining! The lower has a second living area complete with a queen-size bed and a convenient kitchenette. There is an abundance of space for the whole family to relax and have fun. Smart TVs, high-end furnishings and cozy fireplace in the main living. "Solo Fish" is a 10min walk to beach, ensuring an enjoyable escape for everyone.

Guest favorite
Apartment in Middletown
4.89 out of 5 average rating, 19 reviews

Bass Rocks Upper Decks apartment

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.

Top guest favorite
A spacious dining area features a large circular table surrounded by white upholstered chairs. Natural wood walls and exposed beams create a warm atmosphere. A unique wooden horse sculpture adorns one wall, while a cozy sofa and armchairs provide additional seating.
Home in Middletown
5 out of 5 average rating, 76 reviews

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!

Top guest favorite
A cozy living area is presented, featuring a spacious sectional sofa adorned with decorative pillows. A coffee table sits in front, accompanied by wine glasses. A large television is positioned against the wall, with soft natural light filtering in through sheer curtains covering the nearby window.
Apartment in Downtown Providence
4.98 out of 5 average rating, 195 reviews

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!

Guest favorite
A private pool area is surrounded by lounge chairs and umbrella-shaded dining. The two-story house, featuring a light-colored exterior, is complemented by greenery and a spacious deck. Clear blue skies and sunlight enhance the inviting atmosphere of the outdoor space.
Home in Middletown
4.93 out of 5 average rating, 72 reviews

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.

Guest favorite
A rustic cabin with a stone chimney is set against a backdrop of lush trees and a warm sunset. The wraparound porch features wooden railings and is complemented by neatly landscaped areas. A stone wall borders the driveway, leading to the cabin's entrance.
Cabin in Glocester
4.9 out of 5 average rating, 143 reviews

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.

Guest favorite
A two-story house is set against a sunset backdrop, showcasing a spacious deck with wooden railings. A circular pool is visible on the deck, surrounded by a grassy area and decorative fencing, creating a welcoming outdoor space.
Home in Warren
4.91 out of 5 average rating, 67 reviews

Cozy Coastal Escape in Warren | Dog Friendly

Welcome to River's Edge Retreat! With captivating views of the Kickemuit River, our home promises a truly relaxing stay. Unwind in spacious, light-filled living areas, designed with utmost comfort in mind, and enjoy outdoor fun with the refreshing pool, an outdoor BBQ grill, and a cozy outdoor dining area. Located in historic Warren, River's Edge Retreat offers the perfect balance of tranquility, family bonding, and convenient amenities at our idyllic riverside haven.

Guest favorite
A sparkling blue pool is featured in the foreground, reflecting sunlight on its surface. Beyond the pool, a spacious outdoor deck is visible, furnished with lounge chairs, umbrellas, and shaded seating areas, surrounded by lush greenery.
Cottage in Jamestown
4.93 out of 5 average rating, 134 reviews

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.

Guest favorite
A spacious sleeping area features a canopy bed with an orange quilt. Surrounding the room are colorful artworks and wooden sculptures. Natural light enters through windows, highlighting the eclectic decor and greenery from nearby plants.
Home in Scituate
4.94 out of 5 average rating, 250 reviews

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.

Superhost
A scenic view of Newport Harbor showcases a collection of moored boats and yachts reflecting in the calm waters. The surrounding buildings feature a blend of coastal architecture, nestled against a clear blue sky.
Apartment in Newport
4.83 out of 5 average rating, 6 reviews

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

When is the best time to visit Middletown?

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