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Vacation rentals with a pool in Middlesex County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Middlesex County

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guesthouse in Essex

4.82 out of 5 average rating, 28 reviews

Privateers Boathouse (Village Waterfront)

Right in the middle of everything Essex Village has to offer. Very special little waterfront cottage with unrivaled views & access to town is hosting guests. Park your car off-street and enjoy all the wonders of Essex Village by foot during your visit. Secluded, yet utterly central Village location. Short drive to beaches, golf, hikes & more. 🌟 Request a WEEKLY rate 🌟 🛶 Access to swimming pool ONLY WITH ADVANCE ARRANGEMENT 🚣‍♀️ (No onsite kayaks/launch)

Cottage in Guilford

4.95 out of 5 average rating, 174 reviews

Luxury cottage by the sea with hot tub and pool

We built this guest cottage to provide an ultimate luxury experience for people wanting to escape from hectic life!With incredible coastal views, this home is a haven of tranquility. It sits on a special stretch of the Connecticut coast, with spectacular bird and wild life-watching year-round. Enjoy great shopping in Guilford's boutiques around the historic town green. Watch the sun set over the water and relax in the hottub for some night time star gazing year round (pool open June-beg/mid Oct)

Barn in Deep River

4.91 out of 5 average rating, 32 reviews

Zen retreat

You won’t forget your time in this romantic, memorable place. Perfect for a couple that want to retreat to renew and reset. Bathroom has an accujet shower in a steam capsule. Outdoor shower and bath tub in our healing garden. Swimming pool (in season) with a sun deck. Meditation garden and weeping willow will relax and rejuvenate your spirit. Wintertime a sauna is available after we close the pool. Windows and some of the furnishings were last in Katherine Hepburns home. Imagine the stories.

Place to stay in Middletown

4.96 out of 5 average rating, 49 reviews

A Luxury Estate Elegant & Private~White Lion Manor

Escape the frenzy of the world in this family friendly rental, every detail is taken care of, From the garden, saltwater pool, and courtyard views. With over 7,500 sq ft of opulent living space, White Lion Manor is more than a stay it’s a unique experience tailored for those seeking the extraordinary.The 6 person hot tub, sauna, massage chair, and endless amenities will help you Indulge in the opulence of our meticulously curated mansion and immerse yourself in the lavish lifestyle you deserve.

Home in Old Saybrook

5 out of 5 average rating, 45 reviews

3BR Updated Cottage w/ Pool in Old Saybrook

Welcome to Osprey Lookout! 3 bedroom, 1 full bath updated cottage located in the quintessential New England beach town of Old Saybrook, CT. With distant views of Long Island Sound from the pool deck, this single-family cottage in a private setting has everything you need to enjoy a relaxing family vacation, including an outdoor shower to rinse off after a day at the beach! Nearby: - Harvey's Beach - Connecticut Wine Trail - Essex Steam Train - Mohegan Sun & Foxwoods - Historic Mystic Seaport

Home in East Haddam

4.98 out of 5 average rating, 44 reviews

Cloud 9 - Guest favorite! Pool, hot tub, game room

Spacious 5 bedroom 6 bath sleeps 14 -WHAT YOU’LL LOVE- • Private resort style patio, including STUNNING POOL, HOT TUB, fireplace and firepit, bar and grill, 65" TV, outdoor bathroom and shower. • Open concept floor plan that is great for groups and families. • Authentic New England experience. • Fun game room for adults and kids with wet bar and mini fridge • Quiet street and neighborhood. NY times listed East Haddam in their “52 places to love” in 2021 1 mile to East Haddam Center

Villa in Killingworth

5 out of 5 average rating, 14 reviews

1-of-a-kind Estate w/ Pool, Spa, Tennis & Pond

Nestled in nature, this luxurious property is situated on 3.5 park-like acres with two streams that wrap around the house. This one-of-a-kind estate has breathtaking views, deluxe amenities, & comes fully stocked for all your vacation needs. Relax in the comforts of the home or enjoy the blue stone patios, heated gunite pool & spa, private tennis court, or kayaking on the pond. Secluded yet conveniently located, the property is a mere 15 minutes away from shops, restaurants, and the shoreline.

Villa in Guilford

5 out of 5 average rating, 26 reviews

TREETOPS! An upscale, unique 5 bdrm home with POOL

TREETOPS is a 4850 square ft 5 bedroom Mid century Modern perched on an outcropping of granite cliffs, surrounded by 2 acres of beautiful forest. *Property not suitable for children under 8 years old* Stroll along the loop trail in our woods, sit in the garden, have a fire in the fire pit, or relax and get some sun by the marine-blue, stone-decked pool! Birdwatching, breakfast, and evening cocktails are best on the spacious wrap-around deck. Hiking is just steps away at "Westwoods Trailhead".

Apartment in Glastonbury

4.89 out of 5 average rating, 424 reviews

Quiet 2 bed room apt w/ private entrance.

NOTE WELL: This light, spacious basement apartment is located in a residential neighborhood in South Glastonbury near the Connecticut River and many good hiking areas, shops, and restaurants. We are working professionals who rise and retire early. We have a large exuberant dog who is fenced (electric) away from the apartment and house entrances and driveway. The space is not appropriate for parties. Do not inquire or book if your life situation is not amenable to this description.

Vacation home in Westbrook

4.88 out of 5 average rating, 33 reviews

Modern Coastal Home with Pool

Welcome to Salty Marsh! This stylish 3-level home is perfect for just about anyone looking for beautiful sunsets, coastal vibes, and a comfortable and unique vacation. Every inch of this space has been thoughtfully designed and decorated to make you feel at home while on vacation. A perfect location for a family gathering, a few couples get away, girls weekend or any excuse to escape. This unique property offers 3-levels of living with two equipped kitchens.

Home in Clinton

4.9 out of 5 average rating, 10 reviews

Clinton Beach House & Cottage w/ Pool, Near Shore

A block and a half from the water and marinas! Beautiful 4BR/2.5 BA beach area home (sleeps 10), close to marina/town beach. Property includes in-ground pool and 1BR/1BA guest house (sleeps 4). A spacious colonial-style main house and carriage house share a bright sunny half-acre. Fully fenced in backyard makes it idea for families. Backyard fire-pit, new plantings, beach stone, window boxes, and an outdoor shower add to the property's appeal.

Guest suite in Portland

4.95 out of 5 average rating, 21 reviews

Cozy waterview in-law apartment

Take it easy at this tranquil getaway. This in-law apartment offers beautiful views overlooking the CT river. Featuring its own separate entrance the house, outdoor seating, and parking spaces. Next to a marina for easy access to water sports. Location is conveniently between both downtown Middletown and south Glastonbury (about a five min drive either way) and offers a wide variety of restaurants and entertainment. 25 yo age minimum.

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Popular amenities for Middlesex County rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in Old Saybrook

5 out of 5 average rating, 13 reviews

Beautiful Shoreline home in parklike setting

Home in Old Lyme

4.7 out of 5 average rating, 10 reviews

Gorgeous 1700s Home Sleeps 10, 3 bath, Pool

Home in Guilford

5 out of 5 average rating, 5 reviews

Peaceful private home with pool and pond

Home in East Hampton

5 out of 5 average rating, 4 reviews

Direct riverfront luxury home!

Home in Clinton

4.96 out of 5 average rating, 28 reviews

NEW! 5-bedroom historic cottage, near beach

Home in Killingworth

4.75 out of 5 average rating, 4 reviews

Quiet Connecticut Retreat w/ Pool, Deck & Fire Pit

Home in Westbrook

4.73 out of 5 average rating, 132 reviews

Secluded Family escape w/ pool & jacuzzi

Condo rentals with a pool

Condo in Greenport

4.83 out of 5 average rating, 125 reviews

Seaside Escape w Pool, Private Beach + Patio

Condo in Greenport

4.89 out of 5 average rating, 148 reviews

Beautiful Waterview Condo on the North Fork of LI

Condo in Norwich

4.98 out of 5 average rating, 159 reviews

Peaceful Oasis steps from Mohegan Sun

Condo in Norwich

4.97 out of 5 average rating, 118 reviews

The Vacay Villa

Condo in Norwich

4.93 out of 5 average rating, 70 reviews

Spa Creek - Chic Modern Villa near Spa & Casinos

Condo in Greenport

5 out of 5 average rating, 107 reviews

"Breathtaking Waterfront Water's Edge view"

Condo in Greenport

4.92 out of 5 average rating, 137 reviews

Beachside Waterview 2Br Condo w/ Pool in Greenport

Condo in Norwich

4.88 out of 5 average rating, 229 reviews

The N-V ...The Spa at the Norwich Inn.

Home rentals with a private pool

Home in East Hampton

4.73 out of 5 average rating, 15 reviews

Historical Estate Home with Backyard Pool

Home in East Hampton

4.94 out of 5 average rating, 16 reviews

Walk to Water. Stunning Home with Gorgeous Pool & Grounds.

Home in East Hampton

4.98 out of 5 average rating, 128 reviews

Explore the Water & Woods at a Relaxing Retreat

Bungalow in East Hampton

4.93 out of 5 average rating, 107 reviews

East Hampton Ranch with Access to Clearwater Private Beach

Home in Southampton

5 out of 5 average rating, 81 reviews

Best of Country and Beach Living

Home in East Hampton

4.82 out of 5 average rating, 45 reviews

Enchanting Home with Large Decks and Heated Pool

Home in Southampton

4.95 out of 5 average rating, 20 reviews

Perfect Getaway at Sunny Modern Shampton Lake House

Home in East Hampton

5 out of 5 average rating, 13 reviews

Saltbox with Separate Poolhouse in Northwest Woods

Destinations to explore