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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Top guest favorite

An aerial view of a spacious backyard showcases a private swimming pool surrounded by a patio area. Chairs and umbrellas are positioned around the pool, with a barbecue grill nearby. The home features light-colored siding and multiple outdoor seating options, creating an inviting outdoor space.

Apartment in Waltham

4.97 out of 5 average rating, 312 reviews

Cozy Private Studio Unit w/ Laundry and Parking!

Almost every guest describes my place as cozy, which was the feeling I was going for when I designed the space! You'll love this good sized 300 sq. ft PRIVATE 1 bedroom studio. This unit has its own entrance w/ punch code door, full bathroom, large walk-in closet, mini fridge, freezer and microwave. It has one parking spot in the driveway and a washer /dryer. The backyard is shared but the unit has a private patio. Rental is attached to a single family home. (Please note: No full kitchen)

Guest favorite

A private outdoor area features a cold pool surrounded by a spacious patio. Two red umbrellas provide shade over lounge chairs, with a hot tub nearby. The light-colored house, framed by green trees, offers access to a cozy seating area visible at the rear.

Villa in Newton

4.92 out of 5 average rating, 66 reviews

Explore Boston in style! Dream home, pool, sauna.

Relax in this calm, elegant lovely home with fully equipped high-end kitchen, 4 modern bathrooms, private fenced garden with hot tub and cold pool. Conveniently located in South Newton - one of the most desirable and safe suburbs of Boston. 3 minutes walk to a temple, 15-20 minutes drive to downtown Boston, 8 minutes drive to BC, 20 minutes drive to Babson, Bentley, Harvard & MIT. 25 minutes walk to a T (Green line "Newton Highlands"). Great restaurants and shopping areas within minutes drive.

Guest favorite

An outdoor swimming pool is surrounded by a spacious patio and lush greenery. Sun loungers are arranged around the pool, with a shaded seating area nearby. The house features a multi-level deck overlooking the pool, creating a relaxing outdoor space for guests.

Home in Hopkinton

4.95 out of 5 average rating, 153 reviews

Hopkinton Mass 3+ Bedrooms - Great location!

This my home in which I am now an "empty-nester". I have 3 bedrooms available, each with a Queen bed, plus a room over the garage with 2 futons and a mattress. NOTE: I live here and will be home during your stay. You'll have access to a private bathroom and the rest of the house: kitchen, dining room, living room, etc. NO pets allowed My place is close to Boston, Worcester, Providence, state parks, etc. Good for singles, couples, business travelers and families. Great pool and hot tub!

Superhost

A spacious outdoor pool area is surrounded by lounge chairs and tables, offering a relaxing atmosphere. The pool is clear and inviting, with steps leading into the water. A rustic building with large windows is positioned nearby, set against a backdrop of lush greenery.

Cottage in Westford

4.92 out of 5 average rating, 37 reviews

Beach & pond cottage ! Westford MA and Boston!

Summer Village resort is only 20 miles from Boston. Best of both worlds! Your New England style cottage is steps to the beach, Lodge restaurant & bar, heated pools (family & adult), hot-tub, playground, tennis/ basketball/ fire pits pocket parks, golf putt, fishing, 24-hr fitness center. You'll enjoy lake views of Long Sought for Pond from the sun-filled porch, sandy beach, nestled in a beautiful gated seasonal cottage community. CENTRAL A/C !! Queen beds, Bunk bed. Weber outdoor grilling.

Top guest favorite

Guesthouse in Maynard

5 out of 5 average rating, 27 reviews

Cute mill house: 3BR•Wood stove *Brkfst included*

Welcome to the most walkable town in Metro Boston, w/ movie theater, live performance venue, beer garden, galleries, shops, & 17 restaurants 1/2mi from our front door. Our 1910 mill town company house is a little oasis. This is a two-family house; two separate private residences side-by-side. My family occupies the other side. Between house & garage, the outside dining area and fire pit are for your private use. Beyond the garage, we invite you to share our backyard w/ pool and badminton.

Superhost

A welcoming entrance is displayed with a polished brick pathway leading to a well-maintained white house. The front features large black-framed windows and a pair of bold red doors flanked by pots of colorful flowers, complemented by lush green landscaping.

Home in Canton

4.87 out of 5 average rating, 23 reviews

Hidden Gem near Boston w/ Private lake access

Waterfront 3BR home 1 mile from commuter rail to Boston. 1 mile from Blue hills ski. 2.2 miles from New England's 1st and only TopGolf. This 3BR, 2.5 BA features an open floor plan w/ view of your private lake from the kitchen and dining rooms. Head downstairs to play pool, ping pong or darts. Or relax by the fire and watch tv (all streaming channels). Warmer months turns into a resort: Fishing, boating, swimming, grill, fire pit, furnished cabanas, hiking the blue hills and much much more.

Guest favorite

Apartment in Fitchburg

5 out of 5 average rating, 20 reviews

Relaxing Poolside Getaway

Welcome to our charming 1-bed, 1-bath side-by-side unit, a perfect paradise with poolside access available during the warmer months! My husband and I, along with our cat, Mia, live in the main house. Enjoy the TVs in both the living room and bedroom, each offering streaming options, along with a fully equipped kitchen. The futon converts into a full-size bed for additional guests. It’s a great place to unwind, whether indoors or relaxing in the backyard setup. We look forward to hosting you!

Guest favorite

A private pool area features loungers arranged beside a clear water swimming pool. Blue-and-white striped umbrellas provide shade over the seating. A stone wall outlines the space, complemented by leafy shrubs and a dedicated area for outdoor dining and grilling.

Home in Framingham

4.91 out of 5 average rating, 11 reviews

Luxury Boston Ranch –Sleeps 8|Pet+|Private pool

A gleaming, beautiful pool – a rare find in the Boston area – awaits you at this must-visit retreat! This Boston getaway has 4 spacious bedrooms & a fully equipped kitchen that blends luxury and comfort. Relax in the cozy living area, challenge your group in the lively game room, or start your mornings with a specialty brew from the charming coffee bar. Spend your afternoons by the private pool in the serene, pet-friendly yard – the ideal escape for creating unforgettable memories together.

Superhost

Apartment in Boston

4.84 out of 5 average rating, 31 reviews

The Curie-Perfect for Monthly Stays

Experience Boston in a 1 bedroom with comfortable decor and charming feel! Just a 5 min walk from the T and close to Boston College/Harvard/MIT, you can tastefully engage with all of Boston. Unit Features -> Blazing Fast WiFi -> 65” Roku TV Living Room -> 55” Roku TV Bedroom -> Fully Stocked Kitchen -> Washer & Dryer -> Comfortable Queen Bed -> Balcony Ideal for business travelers, couples, nurses, and anyone looking to experience Boston in peace and comfort.

Guest favorite

A clear blue pool reflects the surrounding area, framed by a patio with lounge chairs. A shaded seating area is visible next to the pool, enhancing outdoor relaxation options.

Home in Worcester

4.96 out of 5 average rating, 98 reviews

Courtyard Garden | Pool | BBQ+Fire Tbl | Fireplace

★ "Tania’s place was much more then a place….it was a full on fabulous experience." ☞ Courtyard w. lounge + garden ☞ Patio w/ zen fire table* ☞ Natural gas + charcoal grill ☞ Reverse osmosis water filter ☞ 66” smart TV projector ☞ Air filter + purifier: whole house ☞ Apple Home pod mini's ☞ Indoor gas fireplace ☞ 300+ Mbps wifi For non-smokers. No smoking inside or outside. 8 mins → DT Worcester (cafe, shops, dining) 17 mins → Worcester Regional Airport ✈

Guest favorite

A tranquil outdoor pool area is surrounded by lush greenery, featuring a swimming pool with a waterfall. Colorful chairs in pink and turquoise are positioned nearby, inviting relaxation. A hot tub is situated adjacent to the pool, contributing to the serene atmosphere.

Apartment in Holliston

4.96 out of 5 average rating, 121 reviews

Lake Link

Beautiful fully stocked 2 BR apartment located in Holliston Historic District. Top of the line swimming pool with waterfall and hottub (May 31-Sep 30). Full kitchen, full bath, washer/dryer, central heat and AC, fireplace, wireless internet, Cable TV with almost all premium channels available, private driveway and entrance. Sorry, but no pets allowed. Note: COVID19- We require all eligible guests to be vaccinated or have 72 hr negative test.

Guest favorite

The backyard features a tranquil swimming pool with sunlit reflections, surrounded by elegant outdoor seating arranged on a stone patio. Large windows in the main house offer views of the inviting outdoor space, enhancing the serene atmosphere.

Home in North Andover

4.94 out of 5 average rating, 152 reviews

Nana-tucket Inn

Charming historic town, home of Brooks School and Phillips Academy, 30 minutes to Boston and Seacoast. Families will enjoy our children’s park and town park, just a short walk from property. Enjoy pastural views while relaxing poolside (availability May 1 - Oct 1)in a quiet & private backyard setting. Hot tub is also open May 1 til Nov 1. Seven minutes to commuter rail for those who desire traveling into Boston, no hassle!