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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 $112 CAD 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 and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 80 rentals that welcome pets

  • Rentals with dedicated workspaces

    280 properties have a dedicated workspace

  • Wifi availability

    480 of Middletown vacation 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

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 favourite
A backyard pool area is showcased at sunset, with soft hues reflecting off the water's surface. Surrounding greenery is neatly landscaped, and a basketball hoop is visible in the background. A secured fence outlines the spacious yard, enhancing the sense of privacy.
Home in Portsmouth
5 out of 5 average rating, 18 reviews

Perfect Coastal Escape close to Newport & Beaches!

Located in Portsmouth's desirable Lilac Lane neighborhood, and conveniently located between downtown Newport and Bristol, this beautiful home offers everything you're looking for! Enjoy the sunset as you relax and unwind in privacy on the back deck or by the pool. You'll be surrounded by landscaped gardens and sweeping picturesque farmlands. 6 miles from Historic Newport and Middletown beaches, 2.4 miles from Sandy Pt. Beach, 8 miles from Bristol, and a short drive to many local vineyards!

Guest favourite
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.

Guest favourite
Apartment in Middletown
5 out of 5 average rating, 16 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 favourite
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, 194 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 favourite
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, 71 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 favourite
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, 137 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 favourite
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, 133 reviews

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.

Guest favourite
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, 244 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.

Top guest favourite
A light-filled living space features a curved beige couch, complemented by a green stool and decorative pillow. Lush indoor plants add vibrancy alongside wall art in frames. The cohesive color palette includes soft blues and natural wood accents, creating an inviting atmosphere near an open bathroom doorway.
Home in Middletown
4.93 out of 5 average rating, 122 reviews

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.

Superhost
Apartment in Newport
5 out of 5 average rating, 4 reviews

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.

Guest favourite
A newly built wooden deck features a dining table with four chairs and a lounge area with two cushioned chairs. An umbrella provides shade, while potted plants add greenery. A grill is visible in the foreground, with a glimpse of the pool in the background.
Townhouse in Middletown
4.97 out of 5 average rating, 65 reviews

Townhouse Close to Downtown Newport & Beaches

Two bedroom townhouse in residential neighborhood; 1 mile from historic/downtown Newport (shops/restaurants); 2 miles from Easton's Beach; 2 playgrounds within walking distance; above ground pool, fire pit, 20' furnished deck, grill; plenty of parking; WiFi & apps; central air. It's about a 7 minute uber ride to downtown Newport or Easton's Beach. Shaws/LQ/Starbucks/Dunkin are one mile away in the opposite direction.

Top guest favourite
A spacious wrap-around porch is shown with comfortable seating, offering panoramic views of the waterfront. The warm glow of sunrise reflects on the water, and a distant bridge is visible under a clear sky. The setting invites relaxation and enjoyment of the serene environment.
Home in Somerset
4.99 out of 5 average rating, 186 reviews

Beachfront W/ Hot Tub, Sauna, Pool & Panoramic View

Welcome to the Heart of Somerset! Read our reviews & stay a while! 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. Grab a kayak, or sit back and relax and let the gentle sea breeze wash your worries away!

Popular amenities for Middletown rentals with a pool

When is the best time to visit Middletown?

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