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

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)

World Cup Boston • Pool • Sleeps 4 • Near Airport
Cody’s Place is a clean, comfortable stay mins from Boston, airport & beach - with heated pool & free parking. Thoughtfully hosted for a smooth, stress-free stay perfect for travelers, couples, or a quick getaway seeking convenience, comfort & prime location Private entry basement directly across from the ocean. Enjoy fresh sea air, sunrises & a restaurant steps away • Steps to beach • Mins to Airport • Boston access (ferry/Uber) • Free on-site parking • Fast WiFi + Smart TV • Easy self check-in

The Franklin: Wellness • Aesthetic • W/D • Gym
Experience Boston in this incredible eye-catching studio. Comes with a room divider for 1 bedroom like feel! Just a 5 min walk from the T and close to Boston College/Harvard, you can engage with all of Boston tastefully. Unit Features -> Blazing Fast WiFi -> 65” SmartTV with Streaming -> Fully Stocked Kitchen -> Washer & Dryer -> Comfortable Queen Bed Ideal for business travelers, couples, nurses, those in hospital treatment and everyone looking to experience Boston in comfort and peace.

Oceanfront Pool. Close to Boston. Free Parking.
Enjoy a relaxing & tranquil beach setting while having quick access to Boston and all it has to offer. Stunning ocean views can be seen from our seasonal saltwater pool and all-season hot tub (exclusive during your stay). We are 4 short miles from Boston & public transportation is easily accessible. Winthrop is a welcome relief from the hustle and bustle of the city, where you can come "home" and wind down to the sound of ocean waves, seaside birds, gorgeous sunrises, and beautiful moon rises.

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.

Stylish and Cozy at Revere Beach
Unwind in the stylish Studio apt in the heart of Revere. Enjoy the apartment all to yourself and your family. The city is full of award-winning restaurants, bars, shops, historic landmarks, and attractions. Adventure through Revere and the metro Boston region easily from this prime location with very close walking distance to Blue Line subway station and Revere Beach. ✔ Fully Equipped Kitchen ✔ Comfortable Bedroom w/ Full Bed ✔ Office Desk ✔ High-Speed Wi-Fi ✔ Free Parking ✔ Pool ✔ Gym

Cozy Private Suite halfway between Cape & Boston
Large private room located in the Basement of a single family home. The home is conveniently located less than one minute from route 3 half way between Boston and Cape Cod. The room has a full size bed, and a euro lounger that can be used to relax and watch TV or reclyned for sleeping. There is a kitchenette located in the room which has a Fridge with top freezer, a microwave and a Keurig . The private bath is located inside the bedroom. Cool off in the pool during summer months.

the house of id; vintage shop, accessible space
🏡🚨‼️ Now Featured in The Boston Globe ‼️🚨🏡 Stay. Id's design is informed by our firsthand experience of living with a chronic/invisible illness. To us, accessibility means joy at your fingertips; and participation without overexertion. Unmask. Shop. We did the legwork, filling the house with buyable treasures. Live with the pieces you love. Then take them home. Take Part. Some of the house is experiential. Change hardware. Move art. Bake for the community. Get involved.

Spacious vacation unit in premium suburban town
Weston is one of Boston area's most desirable towns. <30 min to downtown Boston with a lot of open space. Centrally located with easy access to highways, train stations, etc. Next to a park with hiking trails, this is a secondary unit (Duplex units) with its own separate entry/exit. 3 bedrooms (one on lower level, two on 2nd level), kitchen, 2 baths (both on lower level). ~2000 square feet of space. Some seasons (including some winters) we have hens in the backyard...

Private Pool Retreat w/Fire Pit Near Singing Beach
Relax in a private coastal retreat with a pool and fire pit just minutes from Singing Beach. This updated suite offers a clean, modern layout with fireplace, comfortable sleeping space, and is ideal for relaxing stays or remote work. Enjoy a secluded backyard—rare this close to the beach. Located in Manchester-by-the-Sea near downtown, dining, and coastal views. Private entrance, free parking, and fast WiFi. Seasonal pool (5/20–9/8).

Luxury suite, robes/pool/1GB wifi, near Boston
Every detail of this apartment was personally designed by your host. Plush robes, slippers, toothbrush, toothpaste, bottled water, coffee, and laundry pods are waiting for you. Arrive with just your suitcase. 1GB dedicated fiber internet. Pool, gym, BBQ, and study rooms in the building. Garage parking available — rare in Cambridge. Steps to Lechmere Station, MIT, Harvard, and MGH.

Pool Is Open! Steps from Harbor + Walk to Old MHD
HIGHLIGHTS: • Marblehead Harbor - 4 houses away • The Barnacle Restaurant - 4 houses away • Private backyard pool • 0.2 Miles to Fort Sewall • 0.3 Miles to Gas House beach • 0.4 Miles to Old Town Marblehead • 300 Feet to The Barnacle Restaurant • Walkable to restaurants and shopping • Beautiful private garden • 1 King, 2 Twin and 1 Sofa Bed • 2-car off-street tandem parking spaces
Popular amenities for Boston rentals with a pool
House rentals with a pool

Summer heated Pool ~Easy Boston Access! STR-25-22

Pool Is Open! 4-Bed Home w/Pool + Walking Trails

Bauhaus Retreat in Nature Preserve w/ Pool

Boston 15 min away.

Beautiful Spacious 4BRM House!

Weymouth Waterfront Getaway w/ Swim Spa & Hot Tub

Explore Boston in style! Dream home (STR-26-3)

Hidden Gem near Boston w/ Private lake access
Other holiday rentals with a pool

The Murthy : Bright • Spotless • W/D

Hotel-like amenities, all the comforts of home!

Luxury Stay in Somerville | River & City View

Free Parking Close to All Major Boston Attractions

The Crawford: Spacious • Elegant • W/D

Stylish StudioLux in Vibrant East Boston

Spacious 3-BR Furnished Beach Home

The Warren : Groups • Elegant • Cozy • W/D • Pool
When is the best time to visit Boston?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $240 SGD | $258 SGD | $273 SGD | $419 SGD | $424 SGD | $475 SGD | $450 SGD | $436 SGD | $429 SGD | $431 SGD | $287 SGD | $247 SGD |
| Avg. temp | -1°C | 0°C | 4°C | 9°C | 15°C | 20°C | 23°C | 23°C | 19°C | 13°C | 7°C | 2°C |
Quick stats about holiday rentals with a pool in Boston

Total holiday rentals
Explore 450 holiday rentals in Boston

Nightly prices starting at
Boston holiday rentals start at $38 SGD per night before taxes and fees

Verified guest reviews
Over 9,460 verified reviews to help you choose

Family-friendly holiday rentals
170 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 270 rentals that welcome pets

Rentals with dedicated workspaces
260 properties have a dedicated workspace

Wifi availability
440 of Boston holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Boston rentals

4.7 Average rating
Boston stays receive an average rating of 4.7 out of 5 from guests

Nearby attractions
Boston’s top spots include Fenway Park, Boston Common and TD Garden
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Tuckahoe Holiday rentals
- Long Island Holiday rentals
- Montreal Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Pocono Mountains Holiday rentals
- The Hamptons Holiday rentals
- Rentals with breakfast Boston
- Flat rentals Boston
- Rentals with a patio Boston
- Rentals with a kayak Boston
- Rentals with a firepit Boston
- Guest house rentals Boston
- Family-friendly rentals Boston
- Boutique hotels Boston
- Waterfront rentals Boston
- Rentals with a cinema Boston
- Fitness-friendly rentals Boston
- Rentals with lake access Boston
- Rentals with a sauna Boston
- Townhouse rentals Boston
- Rentals with a washing machine and dryer Boston
- Beachfront rentals Boston
- Rentals with a hot tub Boston
- Serviced apartment rentals Boston
- Rentals with beach access Boston
- Hotel rooms Boston
- Bed and breakfasts Boston
- Smoking-friendly rentals Boston
- Pet-friendly rentals Boston
- Rentals with an accessible-height bed Boston
- Rentals with outdoor seating Boston
- House rentals Boston
- Loft rentals Boston
- Rentals with an EV charger Boston
- Private suite rentals Boston
- Apartment rentals Boston
- Rentals with a fireplace Boston
- Rentals with pools Suffolk County
- Rentals with pools Massachusetts
- Rentals with pools United States
- Hampton Beach
- Fenway Park
- TD Garden
- Harvard University
- Boston Common
- Brown University
- New England Aquarium
- Revere Beach
- Boston Seaport
- Northeastern University
- Boston University
- Gillette Stadium
- Freedom Trail
- Boston Convention and Exhibition Center
- MIT Museum
- Canobie Lake Park
- Crane Beach
- Duxbury Beach
- Quincy Market
- Onset Beach
- Roxbury Crossing Station
- North Hampton Beach
- Museum of Fine Arts
- Prudential Center
- Things to do Boston
- Art and culture Boston
- Food and drink Boston
- Sightseeing Boston
- Things to do Suffolk County
- Sightseeing Suffolk County
- Art and culture Suffolk County
- Food and drink Suffolk County
- Things to do Massachusetts
- Food and drink Massachusetts
- Sports activities Massachusetts
- Art and culture Massachusetts
- Sightseeing Massachusetts
- Nature and outdoors Massachusetts
- Things to do United States
- Tours United States
- Sightseeing United States
- Art and culture United States
- Wellness United States
- Food and drink United States
- Nature and outdoors United States
- Entertainment United States
- Sports activities United States







