Holiday rentals with a pool in Middletown

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.

4.93 out of 5 average rating, 152 reviews

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

Escape to our stunning, upscale, renovated home in Middletown, RI! This property boasts a prime location with the beach & downtown Newport just minutes away! With sleeping space for 10 adults + kids, our home offers a private getaway for groups in town for a wedding or seeking a memorable vacation. Lounge by the pool, grill up some food, or snuggle up and watch a movie inside, this home has it all! Make memories that will keep you coming back year after year. Follow us on Insta: Searenity.House

4.95 out of 5 average rating, 189 reviews

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

4.92 out of 5 average rating, 12 reviews

The exterior of the Inn on Long Wharf is captured at twilight, showcasing a modern building with large windows. A flag flutters above, while boats are docked in the foreground. Soft lighting illuminates the structure, blending into the evening ambiance.

Apartment in Newport

Newport 1BR Inn on Long Wharf Seaside Resort

Step back to the days when Newport, RI was a bustling port town and summer retreat for the country's elite. Inn on the Harbor managed by Wyndham is situated in the heart of the Historic Thames St. District, which is lined with unique waterfront shops, art galleries and restored colonial buildings. Visit the Brick Market Place for seaport shopping and dining. Unwind in this spacious one-bedroom resort suite that sleeps up to four guests. The Narragansett Bay is noted for its spectacular beauty.

4.95 out of 5 average rating, 44 reviews

The exterior of a spacious two-story home is showcased, with a white facade and blue shutters. A porch is visible at the front, while the lush green lawn leads towards the waterfront, seen in the background under a clear sky.

Home in Tiverton

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.

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.

5 out of 5 average rating, 46 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!

Apartment in Downtown Providence

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.

4.98 out of 5 average rating, 186 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!

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.

4.93 out of 5 average rating, 67 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.

4.92 out of 5 average rating, 13 reviews

An open-concept living space features a modern kitchen island with seating and stainless steel appliances. Soft lighting hangs above the island, while a comfortable seating area is arranged nearby. Large windows allow natural light to fill the room, complemented by neutral tones throughout.

Home in Portsmouth

5 bedroom house with pool

Enjoy the summer at our spacious home perfect for gatherings with family and friends. Enjoy the beautiful weather poolside or drive 5 to the local beach. We are also a 5 minute drive from the Greendale and Newport Wineries, a 7 minute drive from Newport Polo, and 15 minutes from downtown Newport! With 1 king bed, 2 queen beds, and 4 twin beds, this lovely property offers plenty of space for all guests. Pool open for Memorial Day weekend. 2-3 night minimum, discount for longer stays.

4.89 out of 5 average rating, 108 reviews

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.

4.98 out of 5 average rating, 50 reviews

A charming yellow exterior of a house is framed by leafy green trees and well-maintained shrubs. The entrance features a wooden door with a decorative lantern, complemented by vertical bamboo accents positioned alongside the driveway.

Cottage in Edgewood

The Denison Markham Carriage House

Ideal location! Situated on a grand avenue just steps from Roger Williams Park and a few hundred yards from Narragansett Bay. The Norwood Carriage House is ideal for travelers that want to be close to DownCity Providence (3 miles), all the major hospitals, Brown University, Johnson & Wales, Water Fire events, and the PVD airport. Explore Providence and environs from this beautifully-appointed carriage house filled with art and light. Safe and secure with off-street parking.

4.9 out of 5 average rating, 20 reviews

Holiday Getaway Near Newport & Coastal Golf

Retreat to this radiant 5BR/3 full & 2 half BA coastal home in Middletown, ideal for family gatherings year-round. Whether you're lounging by the sparkling pool, grilling in the outdoor kitchen, or soaking up the summer sun, this spacious home is perfect for warm-weather fun. Explore Newport’s famed mansions and unparalleled dining scene, all just minutes away from this serene all-season escape. This home is the ultimate summer retreat! **HEATED SWIMMING POOL IS NOW OPEN**

4.96 out of 5 average rating, 54 reviews

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

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.

Popular amenities for Middletown rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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.

4.92 out of 5 average rating, 105 reviews

Private Heated Pool | Upscale Oasis Newport & Navy

Home in Narragansett Pier

A charming exterior of a single-story house is displayed, featuring muted blue siding and a centrally located front door framed by white columns. Lush green bushes are neatly trimmed on either side of the entryway, with a manicured lawn extending in front.

5 out of 5 average rating, 85 reviews

Pier Escape

5 out of 5 average rating, 9 reviews

The exterior view of a two-story house showcases light-colored siding and a neatly landscaped yard. Two garages are visible, with a paved driveway leading up to the front entrance. Warm light shines from the windows, presenting a welcoming atmosphere.

Home in North Providence

Minimal Modern Home Getaway

A cozy living room is featured, showcasing a natural stone fireplace and built-in shelving. Light wood flooring complements two white sofas positioned around a central wooden coffee table decorated with a floral arrangement. Subtle artwork and potted plants enhance the inviting space.

Home in Charlestown

5 out of 5 average rating, 3 reviews

Charlestown RI Oasis!

5 out of 5 average rating, 6 reviews

A serene view of the sparkling water is captured, framed by bare trees and lush greenery. The scene is complemented by a well-maintained driveway leading down to the waterfront, inviting tranquility and relaxation.

Home in Portsmouth

Oyster Hill

Home in Narragansett Pier

The exterior of the home features a light gray wood-paneled façade complemented by a teal front door. A well-maintained yard showcases lush shrubbery and a stone pathway leading to the entrance. The sky is bright with scattered clouds, enhancing the inviting curb appeal.

5 out of 5 average rating, 15 reviews

Beach House in the Pier W/ POOL. Book for 2026!

The front of a charming white house is displayed, featuring a pointed roof and decorative trim. Two tall, white-framed windows flank a dark front door, which is adorned with a brass knocker. Lush green bushes border the entrance, complemented by a neatly maintained pathway.

Home in Wickford

4.7 out of 5 average rating, 37 reviews

Waterfront Historic Wickford Village Home!

4.67 out of 5 average rating, 3 reviews

A well-maintained swimming pool is surrounded by lush greenery, with tall hedges providing privacy. A red umbrella offers shade over a seating area, while the landscaped yard includes flowerbeds and a stone feature, creating a serene outdoor space for relaxation.

Home in South Kingstown

Three bedroom home with pool, dogs considered

Condo rentals with a pool

A marina setting showcases a collection of boats docked beside a series of multi-story buildings. Balconies with railings are visible, and the water reflects the surrounding structures. Cloud patterns are observed in the bright sky above, enhancing the waterfront ambiance.

Wyndham Onshore 2 Bedroom

A well-lit bedroom features a spacious bed with a blue accent pillow. Large windows provide a view of Newport Harbor and boats on the water. Sheer curtains allow natural light to fill the room, complemented by neutral-toned walls and a plush carpet.

5 out of 5 average rating, 5 reviews

August Newport Inn on Long Wharf, Waterfront Unit

4.88 out of 5 average rating, 41 reviews

Newport Oceanfront Resorts

An indoor hot tub is encircled by a textured stone area, featuring accessible steps for entry. Large windows allow natural light to illuminate the space, with comfortable seating arranged nearby. A relaxing atmosphere is created by the open layout, enhancing accessibility and enjoyment.

4.9 out of 5 average rating, 10 reviews

Wyndham Long Wharf Resort |2BR King Suite

The exterior of the Inn on Long Wharf is captured at dusk, showcasing a multi-story building with large windows reflecting the evening lights. A wooden boardwalk extends towards the harbor, lined with boats on either side, under a clear sky and gentle harbor breeze.

5 out of 5 average rating, 6 reviews

Timeshare Rental. 3rd floor Condo w/ water view

An indoor swimming pool is featured, surrounded by large windows allowing natural light. A jacuzzi is positioned beside the pool. Several lounge chairs are arranged along the side, providing a relaxing area for guests. The space is clean and well-maintained.

4.84 out of 5 average rating, 49 reviews

1BR Condo w/ Bay Views + Jacuzzi Tub

A modern building is viewed from a wooden dock, surrounded by various boats moored in calm waters. Illuminated windows reflect the evening light, and an American flag flutters gently above. The atmosphere is serene, highlighting the waterfront location.

5 out of 5 average rating, 6 reviews

Ocean Front View! Wyndham Inn on Long Wharf Resort

The waterfront view displays multiple multi-story buildings with varied architectural styles, reflecting in the calm water below. Marina docks are visible in the foreground, surrounded by gentle ripples, creating a serene atmosphere by the water's edge.

4.84 out of 5 average rating, 25 reviews

Ocean Resort

Other holiday rentals with a pool

A spacious and well-lit living area features two grey sofas and a glass coffee table. Large windows allow natural light to fill the room, and a ceiling fan is visible above. The open layout connects to a dining area and kitchen in the background.

Home in Narragansett

4.58 out of 5 average rating, 40 reviews

Beachhouse with Pool, Treehouse + 3 Seasons Room

5 out of 5 average rating, 41 reviews

An aerial view captures the beautiful property surrounded by lush greenery and the Taunton River. The two distinct buildings are highlighted, with a small boat docked near the water, suggesting a serene outdoor area. The landscape features natural vegetation, enhancing the peaceful environment.

Farm stay in Berkley

River Front Farm Style Living