
Holiday 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.

Secluded Oasis w/ Heated Salt Pool - 10 to Newport
🏡 Welcome to your Newport escape - an elegant, sun-filled retreat designed for elevated coastal living: • Heated saltwater pool (late May–Sept) set within our lush, manicured grounds • Beautiful, updated interiors with timeless finishes & thoughtful design • Minutes to 1st & 2nd Beach, Newport Harbor, boutiques, and dining • High-end kitchen ideal for entertaining • Outdoor veranda + deck for alfresco lounging, grilling, & gatherings • Three fireplaces (seasonal) + bonus spaces with games

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.

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.

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.

Bass Rocks Upper Decks, special winter rates
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.

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.

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

Private Heated Pool • Upscale 4BR • 13 min 2 Beach

Cozy Coastal Escape in Warren | Dog Friendly

Minimal Modern Home Getaway

WFH Friendly: Cozy Winter Retreat in Bristol!

Mid-Cent Artist Cape, Pool, 3B, Beaches, 22 Acres

Private POOL, Central AC, Walk to beach, king MBR

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

Waterfront Historic Wickford Village Home!
Condo rentals with a pool

Club Wyndam Newport Onshore Marina sunset views

Wyndham Onshore Waterfront 2/2 & Harbor Balconies!

August Newport Inn on Long Wharf, Waterfront Unit

Newport Oceanfront Resorts

Wyndham Inn on Long Wharf |1BR/1BA King Bed Suite

Newport Onshore Resort Getaway

Wyndham Long Wharf Resort |2BR King Suite

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

Beachhouse with Pool, Treehouse + 3 Seasons Room

North Queenstown

Beautiful South Coast Entire House w/ Pool – MA

Hopeworth Homestead. Sleeps 10+ Pool, Beach, AC

Timeshare overlooking Narragansett Bay

Family-Friendly Beach Getaway

Ocean Cliff I, II May 17 to May 22

Grey Wulf Excursions / Spanish Mastiff Guard
When is the best time to visit Middletown?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $224 NZD | $259 NZD | $273 NZD | $339 NZD | $391 NZD | $561 NZD | $757 NZD | $809 NZD | $793 NZD | $358 NZD | $224 NZD | $224 NZD |
| 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 holiday rentals with a pool in Middletown

Total holiday rentals
Explore 410 holiday rentals in Middletown

Nightly prices starting at
Middletown holiday rentals start at $104 NZD per night before taxes and fees

Verified guest reviews
Over 4,830 verified reviews to help you choose

Family-friendly holiday rentals
230 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
250 properties have a dedicated workspace

Wi-Fi availability
410 of Middletown holiday 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
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