Holiday rentals with a pool in South Boston

4.8 out of 5 average rating, 30 reviews

Flat in Chelsea

Boston Modern Apt: Luxe Stay w/ Gym, Parking

Discover Boston from a contemporary luxury apartment with exceptional ambiance and amenities. STRICT NONSMOKING!!! The Unit: → Lightning Fast Wi-Fi → Comfortable King Bed → Dedicated Corporate Office Workspace → 65" Living Room Smart TV → 55" Bedroom Smart TV → Fully Stocked Kitchen → Washer & Dryer → Private Parking The Amenities: → Business Lounge → Pool → Full Size Gym → Gameroom Ideal for business travelers, travel nurses and corporate clients looking to experience Boston in style.

4.97 out of 5 average rating, 336 reviews

Flat in Waltham

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)

4.96 out of 5 average rating, 313 reviews

Flat in Winthrop

Cody's Place Boston Airport Pool/Beaches ParkFree

Retreat, relax, & refresh in your own private entry basement in law apartment of our well bunkered Beach House. BEST LOCATION across from the mighty Atlantic & Iconic Winthrop Arms Hotel/Restaurant. Take in the salty air & breathtaking sunrises. Steps from Ocean Sunrise & Sandy Beach Surf. Walking distance to public transport, restaurants, parks, or Uber/Walk to the center bars & other attractions. Vacation living. Ferry minutes to downtown Boston. 1 of 3 officially licensed AirBnB's in town.

4.96 out of 5 average rating, 245 reviews

Flat in Winthrop

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.

4.96 out of 5 average rating, 53 reviews

Flat in Charlestown

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

4.84 out of 5 average rating, 165 reviews

Flat in East Boston

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

Cottage in Lakeside Marblehead

4.98 out of 5 average rating, 120 reviews

House with Pool, 4 Houses from Harbor, Fort Sewall

Marblehead Harbor is just 4 houses away from this beautiful antique home with a backyard pool in Old Town Marblehead. This quaint cottage is surrounded by a beautiful garden and is just steps away from The Barnacle Restaurant. Walkable to attractions like Fort Sewall, Fort Beach, Gas House Beach and local shops and restaurants. Car-free convenience in Old Town Marblehead. Perfect for couples or families seeking a charming and convenient getaway that offers off-street parking.

4.9 out of 5 average rating, 104 reviews

Flat in Malden

Luxe Serene 1BR 15 min from Boston with Gym & More

You will love this beautifully designed 1 Bedroom 1 Bath luxury unit that is in a central location between many great cities! You will be staying in a gorgeous private community with a gym, pool table, dog park, kids playground, tennis court, and tons of outdoor space. Have peace of mind knowing you’re in a safe space. Our luxury suite has a Queen Medium Firm bed along with a Queen Air Mattress for any additional guests. Check out more of our amenity spaces below!

4.88 out of 5 average rating, 17 reviews

Flat in Brighton

The Lister-Luxurious Studio Near Heart of Boston

Stylish Studio Minutes from Downtown Boston! Stay just 5 minutes from the T and 10 minutes from Harvard & Boston College. This modern studio features ultra-fast WiFi, a 65" Roku TV, a comfy queen bed, a full kitchen, and an in-unit washer/dryer. Enjoy access to premium amenities including a gym, lounges, and co-working spaces. Ideal for nurses, couples, and business travelers. Walk to top restaurants, bars, shops, and Whole Foods. Parking is available upon request!.

4.96 out of 5 average rating, 121 reviews

Flat in Holliston

Loch 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.

4.82 out of 5 average rating, 45 reviews

Flat in Somerville

Lovely 2- bedroom serviced apartment with pool

Apartment is located at Assembly Row in Somerville. Walking distance from shops, restaurants, medical centers and the Public Transportation (Orange Line). Ideal for traveling nurses, or long stays. The apartment complex has working space, gym, pool and an outside patio. 12 minutes from the Logan airport and 12 minutes from downtown Boston.

Guest suite in Manchester-by-the-Sea

4.9 out of 5 average rating, 162 reviews

Modern Space With Pool Close To Singing Beach

Situated in a very quiet neighborhood, you will rest comfortably. Drive five minutes and you can be in downtown Manchester-By-The-Sea with singing beach and great restaurants. secluded back yard with fire pit and pool. Inside you'll find a freshly updated and modern living space with fireplace. (Pool open from 5/27-9/8).

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Popular amenities for South Boston rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 18 reviews

Home in Hull

NEW! Walk To Beach! Sunshine House

TraciRating, 5 stars3 months ago

We had a Great Stay for a Few Days from Texas! The house is super Cute, and Perfect to have Family gathering. Thanks for welcoming us into Your Bnb!

5 out of 5 average rating, 19 reviews

Home in Newton

Villa with private Pool in Boston's Elite Enclave

JonRating, 5 stars3 weeks ago

Great option when staying in Newton and right down the street from an incredible entrance to a hiking trail. Serge was a great host and kept us informed the entire trip.

Home in Lakeside Marblehead

5 out of 5 average rating, 17 reviews

Large Pool, Nature Trails, Redd's Pond, 4-Bed

AlanaRating, 5 stars3 weeks ago

Amy was very responsive and communicative. The house was clean and maps took us right to the home. It was too early in the season to enjoy the pool but it was pristine and would have been great for hot summer weather. Amy was wonderful with trying to accomodate any requests and we liked the location from easy access to Salem and within a one hour drive to Boston!

Home in Revere

4.8 out of 5 average rating, 54 reviews

Boston 15 min away.

MelissaRating, 5 stars11 months ago

This is the third year we were able to rent Ediangela’s house. As always it’s beautiful and clean. The pool is spotless. Plenty of space for big groups and absolutely perfect for families with kids of all ages. There’s so much to do on the property itself. She is so kind and responsive. It’s always been amazing every time we stay. It’s becoming our summer staple to come and stay by the pool for a few days of vacation. 10/10 absolutely worth renting this space. This year we brought two 10 year olds, a 5 year old, and a 2 year old, with 4 adults. They had the best time in the little play houses and pool. The adults had a great time as well. If you’re looking for a low key - big fun spot where you don’t have to run around to entertain, this is perfect! Everything you need or may need is on site or minutes away if you need to shop. Including the actual beach. I sincerely hope we get the chance to make it year 4 next summer!

4.94 out of 5 average rating, 34 reviews

Home in Arlington

Beautiful Spacious 4BRM House!

NicholasRating, 5 stars1 week ago

I loved everything Maxine said and how she helped navigate around every even in the house, everything was so clean, very quite place good for professional working, everything was just beyond, amazing & lovely place you feel right at home with so much space to move around the house. Being free having your privacy. Thank you Maxine 🙏👏🏽

4.95 out of 5 average rating, 44 reviews

Home in Norwood

the house of id; vintage shop, accessible space

JasonRating, 5 stars1 week ago

Super fun and eclectic house! What really made the stay were the owners, they are thoughtful and very responsive, they clearly care a lot about their guests!