
Vacation rentals with a pool in Middletown
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Middletown
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Beachfront W/ HotTub, Sauna, Pool & Panoramic view
Welcome to the Heart of Somerset! 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 of the Braga Bridge, Mt. Hope Bridge & Bay, Bristol, Tiverton Rhode Island & the Fall River cityscape on the horizon. Grab a kayak or relax, soak up the sun & let the gentle sea breeze wash your worries away!

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

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.

Bass Rocks Upper Decks
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.

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.

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**

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.

Jamestown: Coastal Cozy Cottage in town pets OK
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.

Vineyards, Newport, Narragansett, In-Ground Pool
Wickford area of North Kingstown , 5 minutes to Gooseneck Vineyards. Clean, Smoke Free Home w/room to spare! Large 4 bed/3 bath with pool and cabana, central a/c, 15 minutes from Narragansett, Newport. Short 5 minute ride to NK town beach. If you're not in the mood for the beach, relax in the in-ground pool. (Seasonal May-Sept)10 minutes from TF Green airport and Wickford Train station, 10 minutes to University of Rhode Island. In the middle of EVERYTHING!

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
House rentals with a pool

HUGE family house. Sleeps 10+ Pool, Beach, AC

Private Heated Pool | Upscale Oasis Newport & Navy

Pier Escape

Minimal Modern Home Getaway

Charming Victorian Farmhouse, Inground Pool

Charlestown RI Oasis!

Oyster Hill

Beach House in the Pier W/ POOL. Book for 2026!
Condo rentals with a pool

Wyndham Onshore 2 Bedroom

August Newport Inn on Long Wharf, Waterfront Unit

Wyndham Long Wharf Resort |2BR King Suite

Timeshare Rental. 3rd floor Condo w/ water view

Newport Resorts

1BR Condo w/ Bay Views + Jacuzzi Tub

Ocean Front View! Wyndham Inn on Long Wharf Resort

Wyndham Inn on Long Wharf |1BR/1BA King Bed Suite
Other vacation rentals with a pool

Beachhouse with Pool, Treehouse + 3 Seasons Room

River Front Farm Style Living

CityView 1BR/Pool/Gym/Parking

Newport 2BR Long Wharf Waterfront Resort

Superior 1BR suite @ Wyndham Long Wharf Resort

Jamestown-The Newport Overlook OceanView TownHouse

Beautiful 2-story Apartment in Oceancliff

Newport 3BR Long Wharf Waterfront Resort
When is the best time to visit Middletown?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$26,991 GYD | G$31,176 GYD | G$32,849 GYD | G$40,800 GYD | G$47,077 GYD | G$67,582 GYD | G$91,225 GYD | G$97,502 GYD | G$95,619 GYD | G$62,351 GYD | G$40,173 GYD | G$29,920 GYD |
| 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 |
Quick stats about vacation rentals with a pool in Middletown

Total vacation rentals
Explore 400 vacation rentals in Middletown

Nightly prices starting at
Middletown vacation rentals start at G$16,739 GYD per night before taxes and fees

Verified guest reviews
Over 4,520 verified reviews to help you choose

Family-friendly vacation rentals
220 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
240 properties have a dedicated workspace

Wi-Fi availability
400 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
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- Foxwoods Resort Casino
- Brown University
- Charlestown Beach
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- Craigville Beach
- Point Judith Country Club
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- Ocean Beach Park
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