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 €70 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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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

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.

4.9 out of 5 average rating, 10 reviews

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

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!

5.0 out of 5 average rating, 83 reviews

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

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!

4.98 out of 5 average rating, 195 reviews

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

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.

4.93 out of 5 average rating, 76 reviews

Guest favorite

Apartment in Middletown

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.

4.95 out of 5 average rating, 19 reviews

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

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.

4.9 out of 5 average rating, 147 reviews

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

Jamestown: In town cottage near beach and Newport

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.

4.93 out of 5 average rating, 135 reviews

Top 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

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.

4.94 out of 5 average rating, 265 reviews

Top guest favorite

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

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.

4.94 out of 5 average rating, 130 reviews

Guest favorite

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

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.

4.97 out of 5 average rating, 70 reviews

Top guest favorite

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

Beachfront W/ HotTub, 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!

4.99 out of 5 average rating, 197 reviews

Superhost

An aerial view captures a renovated home surrounded by lush greenery. A spacious deck with seating and a dining area adjoins a clear swimming pool, highlighting the outdoor space. The property is bordered by mature trees, creating a serene environment.

Home in Middletown

Modern Home w/ Pool & Game Room | Mins to Newport

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.

4.91 out of 5 average rating, 199 reviews