Vacation rentals with a pool in Brewster

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Brewster

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

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Guest favorite

Condo in Mashpee

4.97 out of 5 average rating, 101 reviews

Sleep 6 @ New Seabury w/ Pool Access, All Seasons!

Welcome to our beautiful Cape Condo located in The Mews at New Seabury Country Club in Mashpee, MA. Our unit provides access to a private condo association pool a 3 min walk from the unit. Also, we have: -5 min bike/car ride to beach -2 bicycles available for use -Central air, wifi, cable, gas grill -Located on Championship Golf Course -Beach chairs, beach towels/toys -New Seabury Village restaurants, mini-golf, bowling, museums -20 min drive to Hy-Line Ferry to Nantucket/Martha's Vineyard

Feb 8 – 15

ﺩ.ﺇ649 per night

Guest favorite

Condo in Brewster

4.97 out of 5 average rating, 39 reviews

Ocean Edge 2 Bed 2 Bath, Golf & Resort Free Access

Enjoy this 1,000 SF, 2 bed, 2 full new marle tile bathrooms, 2 showers, at Ocean Edge, right in the middle of the golf course. This Airbnb is a full member of the Ocean Edge Resort and allows you access to Ocean Edge golf, and free resort access included up to 6 guests to swimming pools, tennis, gym & pickleball. No one lives here, it is absent of personal items. From the moment you enter, you will know that you have made a great choice and that your time here will be above your expectations.

Nov 12 – 19

ﺩ.ﺇ947 per night

Guest favorite

Condo in Brewster

5.0 out of 5 average rating, 52 reviews

Ocean Edge Resort/Pool access/2bedroom-2bath Condo

Recently renovated end unit townhouse located in the heart of The OE Villages. Beautiful views towards the golf course, and southern exposure with lots of natural light, A/C, W/D and private patio with Weber grill and outdoor furniture. Sports Membership so Guest passes are available for purchase at Linx for use of pools, hot tubs and gyms. Additional costs for use of courts may apply. Bike rail trail, Ice cream store, great restaurants, coffee, beaches and Kayak/Bike rentals are all close by.

Jan 10 – 17

ﺩ.ﺇ1,805 per night

Superhost

Condo in Brewster

4.83 out of 5 average rating, 18 reviews

Ocean Edge: 2 bed/2 bath - Pool/Gym, Near Beaches

Welcome to our spacious and well-appointed 2-bed, 2-bath condo with a private patio overlooking the golf course at Ocean Edge Resort. Access to resort amenities (additional fees apply) and restaurants. We acquired this condo in 2023 and are excited to host you! Perfect for families with kids or a group of friends! You will be a short walk from Ellis Landing Beach and CC Rail Trail and a short car ride away from 10 Brewster bay beaches. Route 6A offers shops, restaurants, art galleries and more!

Jun 20 – 27

ﺩ.ﺇ1,176 per night

Guest favorite

Condo in Brewster

4.97 out of 5 average rating, 158 reviews

Ocean Edge Resort-Pool Access-End Unit-2 bdr/2 bth

2nd floor Ocean Edge end unit condo located in the heart of Brewster with access to OE resort amenities: pools, gyms, tennis courts, as well as access to resort activities (fees apply). Easy access to Cape Cod Rail Trail for bicycles. Scenic route 6A offers arts & crafts galleries and local shops. A 10 minute car ride to a 36 hole Captains Golf course. Short ride to 10 Brewster bay beaches famous for tidal flats. A 30 minute ride to Cape Cod National Sea Shore. Welcome to your Happy Place!

Nov 20 – 27

ﺩ.ﺇ1,028 per night

Guest favorite

Apartment in Wellfleet

4.97 out of 5 average rating, 34 reviews

Rock on Wellfleet!

A wonderful Wellfleet location! This second floor rental has a spacious bedroom with a queen bed, bathroom with a tub and living area with a well stocked kitchen. You would have the whole upstairs to yourself with a private door to come and go. You are also invited to use our pool at anytime! We're located very close to the Cape Cod Rail Trail for miles of bike riding, PB Boulangerie Bistro, Marconi Beach, the iconic Wellfleet drive-in and so much more. Bedding, towels and essentials provided.

Jan 7 – 14

ﺩ.ﺇ547 per night

Guest favorite

Condo in Brewster

4.84 out of 5 average rating, 31 reviews

Golf Course Views and Pools

Enjoy your Cape Cod vacation in Brewster, MA by staying in a cozy and bright condo unit. The unit itself is overlooking hole #12 on a beautiful golf course, owned by well-known Ocean Edge Resort. Lined with plenty of trees there is privacy and quietness, perfect for sitting on the outdoor balcony underneath the stars with a relaxing glass of wine. Part of a country club, you have access to multiple indoor/outdoor swimming pools, gym, saunas, hot tubs, golf course, and restaurants for a fee.

May 22 – 29

ﺩ.ﺇ542 per night

Guest favorite

Cottage in Sandwich

4.92 out of 5 average rating, 131 reviews

Blue Anchor Cottage - private hot tub getaway!

This newly renovated cottage is an amenity-filled launching point to explore all of Cape Cod! Just 0.4miles to the beach and with our own salt water pool, you’ll be able to fully enjoy the Cape's most historic town. Some of our favorites nearby: 2min- your local coffee shop 2min- great fish tacos + bar 2min- nice conservation area hike 2min- local convenience store 7min- downtown Sandwich 7min- golf course 9min- Sandwich Boardwalk 10min- Heritage Museums & Gardens 22min- Cape Cod Rail Trail

Oct 14 – 21

ﺩ.ﺇ1,269 per night

Guest favorite

Apartment in Dennis

4.88 out of 5 average rating, 16 reviews

Pool condo in Dennis Village, 4 mins to Mayflower

Relax in this calm, stylish, new, fully equipped 1 BR condo. “Cape Storia d’ Amore” is 4 mins from Mayflower in the heart of Dennis Village. Located less than 5 minutes from The Merc, Scargo, Oliver's & Planck's Tavern & more. 12 minutes from Cape Cod Inflatable Park. Large, fully enclosed pool is just steps away. new: - kitchen with new range, DW, fridge, Keurig/drip coffee maker, cookware. New bathroom w/walk in shower, washer & dryer. Smart TV, Roku, internet, fireplace, AC in summer.

May 10 – 17

ﺩ.ﺇ563 per night

Guest favorite

Apartment in Hyannis

4.89 out of 5 average rating, 102 reviews

Great Location. Near Beach & Main Street. Unit M1

Our home-away-from-home accommodations include this charming studio with lawn space, a private deck with outdoor furniture and a gas grill. The cottage is comfortably furnished and features a small kitchen. This cottage has a queen bed and a table with sitting area. The kitchen is nicely updated with updated with beautiful granite countertops and stainless steel appliances including an stove/oven, microwave, mini-fridge, toaster, coffee maker, and kettle. This studio has air conditioning.

Jul 12 – 19

ﺩ.ﺇ1,049 per night

Superhost

Condo in Brewster

4.87 out of 5 average rating, 23 reviews

Stylish Ocean Edge Condo #TheCouplesNest

Experience Cape Cod from our stylish 2nd floor condo in Fletcher Village at Ocean Edge, Brewster. Centrally located, it offers easy access to beaches, the Rail Trail, and local dining. Enjoy amenities like pools, tennis, and golf. The modern condo features a fully equipped kitchen and a balcony, perfect for relaxation or adventure throughout the year. Whether you're biking on scenic trails or relaxing by the pool, our condo provides the ideal setting for a memorable Cape Cod experience.

Nov 9 – 16

ﺩ.ﺇ848 per night

Superhost

Townhouse in Brewster

5.0 out of 5 average rating, 3 reviews

Coastal Oasis: Brewster-Cape Cod

Beautiful Townhome in the Villages of Ocean Edge Resort in Brewster with golf course view and a meticulous landscape. You'll have access to outdoor & indoor pools, tennis & pickleball courts, kayaking, beach volleyball court, bike rentals & many club activities (fees apply). Easy access to Cape Cod Rail Trail, route 6A with local shops, art galleries and much more! Brewster and Orleans Beaches are minutes away, with their famous tidal flats and breathtaking sunset.

Nov 9 – 16

ﺩ.ﺇ1,425 per night