
Holiday rentals with a pool in Middletown
Find and book unique homes with a pool on Airbnb
Quick stats about holiday rentals with a pool in Middletown

Total holiday rentals
Explore 480 holiday rentals in Middletown

Nightly prices starting at
Middletown holiday rentals start at €70 per night before taxes and fees

Verified guest reviews
Over 5,480 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 80 rentals that welcome pets

Rentals with dedicated workspaces
280 properties have a dedicated workspace

Wifi availability
480 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
Top-rated rentals with a pool in Middletown
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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.

Oyster Hill
Fall in love with the Ocean State from this gorgeous 4-bedroom, 3-bath vacation home. Situated close to all that Aquidneck Island is known for — Steps from the Glen Manor Mansion, walking distance to Newport Polo, 15 minutes to downtown Newport, the Cliff Walk, and numerous beaches — this home away from home is ideal for who love life by the sea. After exploring, curl up with a good book in the sitting room or work remotely from the home office. Most rooms come with sparkling ocean views!

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!

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!

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.

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.

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.

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.

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.

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.

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.

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
House rentals with a pool

Island Escape with Salt Water Pool

Cozy Coastal Escape in Warren | Dog Friendly

Barrington Oasis: Waterview with an Inground Pool!

Minimal Modern Home Getaway

Family-Friendly Beach Getaway

Vitamin Sea Pier Beach House POOL. Book Fall 2026!

Three bedroom home with pool, dogs considered

Summer Getaway
Apartment rentals with a pool

Newport Resorts

Wyndham Long Wharf | 3BR/2BA King Bed Suite

Wyndham Long Wharf Resort |2BR King Suite

1BR Condo on Long Wharf Waterfront

Wyndham Newport Onshore|1BR/1BA Balcony King Suite

1 Bedroom at Club Wyndham Inn on The Long Wharf

2BR Newport Oceanside Condo Resort w/2 Pools!

Timeshare Rental. 3rd floor Condo w/ water view
Other holiday rentals with a pool

Mali's Place

Boutique Luxury Waterfront w/Pool & Sunset Views

Hot Tub/Pool/FirePit Near NFL Gillette/Xfinity/PVD

Vineyards, Newport, Narragansett, In-Ground Pool

★2 BEDROOM SUITE★ Wyndham Newport Onshore Resort!

Newport Waterfront 1 Bedroom

Modern, Bright, Private Studio w/POOL

NEW ENGLAND SEAPORT ESCAPE in our 2 Bedroom Deluxe
When is the best time to visit Middletown?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | €109 | €116 | €128 | €170 | €197 | €282 | €381 | €407 | €400 | €180 | €113 | €113 |
| 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 |
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- Gillette Stadium
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