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Vacation rentals with a pool in Milford

Find and book unique homes with a pool on Airbnb

Quick stats about vacation rentals with a pool in Milford

  • Total vacation rentals

    Explore 20 vacation rentals in Milford

  • Nightly prices starting at

    Milford vacation rentals start at ﺩ.ﺇ 257 per night before taxes and fees

  • Verified guest reviews

    Over 60 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Milford vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Milford rentals

Top-rated rentals with a pool in Milford

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

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Top guest favorite
The exterior of a rustic wooden house is surrounded by lush greenery and trees. A small fenced area is visible near the entrance, where a welcoming front door can be seen. The building features windows and a gabled roof, set in a tranquil natural environment.
Farm stay in Thompson
5.0 out of 5 average rating, 261 reviews

Rustic Farmette Studio w/yearround Hot Tub

Relax and rejuvenate at this unique getaway on 20 acres in CT’s Quiet Corner. Just an hour from Boston, Providence, & Hartford, enjoy this private in-law studio with beautiful forest views. Lounge in bath robes & soak in the hot tub, take a walk along the trails, enjoy local vineyards, or explore antiques. Folks from all backgrounds and identities are welcome at The Farmette. Ideal for couples, solo travelers, or a family with a young kid. Please include all individuals (&pets) in your booking.

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Top guest favorite
An outdoor lounge area features a circular table surrounded by curved sofas adorned with cushions. Soft curtains frame the space, while potted flowers add vibrant color. Natural light filters through the overhead structure, creating a relaxed atmosphere for gatherings.
Home in Worcester
4.97 out of 5 average rating, 129 reviews

Gather, Cook & Unwind, 3BR, Fireplace

A private resort — without leaving Worcester. Heated pool, fire table, garden courtyard … your own enclosed escape. ★ "Tania’s place was much more than a place….it was a full on fabulous experience." 🏊Heated Pool (to 81F) 🌿 Courtyard w. lounge + garden 🔥Patio w/ Zen fire table* 🍽️ Natural gas + charcoal grills 💧 Reverse osmosis water filter 66” smart TV projector ❄️ Central air conditioning 🔥Indoor gas fireplace 📶300+ Mbps WiFi For non-smokers. No smoking/vaping inside or outside.

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Superhost
Apartment in Charlestown
4.87 out of 5 average rating, 191 reviews

Lux 2BR Apt w/ Pool and Gym

Welcome to your perfect getaway! Our space combines the comforts of home with luxurious amenities to make your stay truly special. Highlights: • Conveniently close to Downtown Boston • Meticulously deep-cleaned before every stay • Complimentary gourmet coffee, fresh linens, and premium bathroom essentials • 24/7 access to a state-of-the-art fitness center • Modern yoga studio and high-tech training equipment • Experience the charm of Somerville while enjoying hotel-quality amenities at home.

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Top 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, 179 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 4 futons/mattresses. 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!

ValueFamilyHospitality

Guest favorite
A well-lit living area features a cozy white sectional sofa and a stylish floor lamp. Light from large windows illuminates the space, highlighting the warm wooden wall design. A round mirror complements the room, while a small table is adorned with decorative plants.
Apartment in Brighton
4.96 out of 5 average rating, 159 reviews

The Murthy : Bright • Spotless • W/D

Enjoy Boston in this elegant suite for long and short stays. Just a 5 min walk from the T and close to Boston College/Harvard, you can tastefully engage with all of Boston. Unit Features -> Blazing Fast WiFi -> 65” Roku TV Living Room -> 50” (x2) Roku TV Bedroom -> Fully Stocked Kitchen -> 2 Queen Bed -> 1 Twin Bed -> 1 Sleeper Sofa Rolling cot and air mattress available on request! Ideal for business travelers, couples, nurses, and everyone looking to experience Boston in style!

ValueFamilyIndoor spaces

Top guest favorite
A historic stone farmhouse is set on a spacious green lawn, complemented by a vibrant red barn in the background. Tall trees provide shade, and a carefully arranged stone border outlines the lush garden area, creating a tranquil outdoor setting.
Farm stay in Hopkinton
4.96 out of 5 average rating, 166 reviews

1790 Stone Manor Farm

This historic New England farm and home is on almost 7 acres of land with mature gardens and places to hike, it is a warm and inviting place to spend lovely summer days by the pool and enjoy warm nights by the fire in the fall and winter. Kitchen and bathrooms all renovated. Located centrally in Ma- 90/495 interchange. Located 45 minutes from Boston, beach, history, mountains, lakes, & NE sports. This home is in historic Hopkinton, where the Boston Marathon starts, center of MA.

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Top guest favorite
A bright bedroom features a spacious bed with a white coverlet and colorful pillows. Natural light filters through multiple windows, enhancing the wooden accents of the walls and furniture. A television is mounted on the wall above a wooden dresser, creating a comfortable and inviting space.
Guesthouse in West Roxbury
4.95 out of 5 average rating, 216 reviews

Country Cottage in the City

This poolside cottage is a country retreat in the city. We are nestled into a small bit of woods on top of the "hill" as it is called locally. The cottage is a studio apartment that has a microwave and mini-fridge as well as sitting area and table. It has a lovely view of the pool and gardens. Besides the pool, there are two garden ponds where we keep ornamental fish. Outside the garden fence there is often a parade of various types of birds, bunnies and even wild turkeys and deer.

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Top guest favorite
A spacious exterior view showcases a two-story light gray house with a brick chimney, set against a backdrop of lush greenery and a mix of trees. A charming barn is visible in the distance, complementing the well-maintained gardens and open lawn.
Apartment in Groton
5.0 out of 5 average rating, 108 reviews

Farmhouse Guest Apartment

Welcome to our quiet private guest apartment! Our property, is surrounded by fields, woods, gardens, and a pond. You will enter through a shared entrance & stairway to the second floor in our home, but have an entire 725 sq. ft. guest apartment all to yourself that includes a living room, full kitchen, bathroom, and large bedroom with a desk. It has ample light with views of fields, stone walls, Christmas trees and our barn. Out back we have a pool, table & chairs you may use.

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Superhost
A small seating area is presented with a pink loveseat adorned with patterned pillows, positioned beside a bedside table. A soft lamp is placed atop the table, and a tissue box is situated nearby. Light wood flooring complements the neutral color scheme.
Guest suite in Framingham
4.78 out of 5 average rating, 104 reviews

Exquisite 1 Bedroom Suite-Charming,W/Private Entry

An exquisite and convenient I BR Modern suite nestled between Boston and Worcester is available for you. Bright and charm w/ a . Beautiful kitchen, remodeled bathroom and a bedroom. Private entrance w/ it’s lovely courtyard to sit outdoor, a free parking spot/ WiFi. The apartment is conveniently located to Babson and Wellesley College, both within 7 miles , FSU is 1 mile train station 2 miles , easy drive to Cape Cod. For all travelers & enjoy your stay her !

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Top guest favorite
A spacious sleeping area features a canopy bed with an orange quilt. Surrounding the room are colorful artworks and wooden sculptures. Natural light enters through windows, highlighting the eclectic decor and greenery from nearby plants.
Home in Scituate
4.95 out of 5 average rating, 259 reviews

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.

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Top guest favorite
The living room features floral patterned sofas arranged around a wooden coffee table. A decorative fireplace is framed by white molding, above which hangs a painting depicting a serene landscape. Natural light enters through two windows, with a basket and various items adding to the homey ambiance.
Home in Burrillville
4.87 out of 5 average rating, 186 reviews

Great country getaway

Quiet country 1895 victorian living.House is in a small neighborhood on a main road across from a cemetery. All bedrooms are located on the 2nd floor, may not be suitable for those with mobility issues,family owned wineries nearby and a micro brewery. 20 min to major highway. Small downtown village area with restaurants and groceries. 30 min from Bryant University and about one hour from Newport, Boston and beaches. Hosts live two houses away

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Top guest favorite
A modern kitchen features white cabinetry and granite countertops, equipped with a refrigerator, microwave, and stove. A small dining table is set with white chairs, and a potted plant adds a fresh touch. Natural light enters through a nearby window.
Guest suite in Brooklyn
4.94 out of 5 average rating, 238 reviews

Affordable In-Law Apartment in Brooklyn, CT

This is a great in-law style apartment which was fully renovated in 2020. It can be booked for short stays or more lengthy visits to Northeast CT. The apartment is one minute from Scenic route 169 and Route 6. It is 30 minutes to UCONN and ECSU. We are close toThe Pomfret School/Rectory School. It is 35 mins to Mohegan Sun and Foxwoods. My place is rural and peaceful. It is good for couples, solo adventurers, business travelers, and families.

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Popular amenities for Milford rentals with a pool