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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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A bright kitchenette area features light wood cabinetry and a blue countertop. Three wooden bar stools are positioned at the counter. A ceiling fan hangs above, and a flat-screen TV is mounted to the wall. Sliding glass doors open to an outdoor view.

Apartment in Dennis Port

4.77 out of 5 average rating, 30 reviews

Beachside Condo with Balcony - Oceanside Condos

This charming Cape Cod oceanside condominium unit is located only a few steps from the warm waters of Nantucket Sound. Offers a heated fresh-water pool, BBQ grill with outdoor table, high-speed wifi, cable, and 2 TVs. Do your own cooking with the fully furnished kitchenette (stove, refrigerator, microwave, coffeemaker, and utensils), or go out to the local restaurants, ice cream sundaes, go-carts, mini-golf, batting cages, kayaking, & jetskiing. This comfy unit has a Queen bed & pull-out futon.

The living room features two comfortable sofas adorned with colorful cushions, situated around a wooden coffee table on a vibrant area rug. Natural light fills the space, highlighting the dining area and fully equipped kitchen visible in the background.

Condo in Brewster

4.85 out of 5 average rating, 54 reviews

Ocean Edge: 2 bed/2 bath - Pools & Resort Access

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!

Top guest favorite

Condo in Brewster

5 out of 5 average rating, 85 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.

Top guest favorite

A spacious backyard is highlighted by a private, unheated in-ground pool surrounded by paved areas. Colorful lounge chairs and an inflatable float add to the inviting atmosphere. A patio table with patterned cushions is positioned nearby, offering a space for relaxation and outdoor dining.

4.95 out of 5 average rating, 127 reviews

Private Pool, near beaches, 3 BR/3 BA, Central Air

Enjoy the Barnstable historic seaside village of Cotuit in this sprawling house with central air, nestled in the pines on a quiet street with private gated (unheated) pool, lg. backyard, firepit, ample parking, just blocks from Main St, Ropes Beach, scenic ocean views, fort playground, and Kettleer baseball. Each bedroom has a TV and ensuite bathroom! Relax in the seasonal sunroom overlooking the pool; grill burgers on the patio. Max. 9 (6 adults). Pool open 6/20-9/15/24. The reviews tell all!

Condo in Brewster

4.97 out of 5 average rating, 191 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!

Top guest favorite

Apartment in Wellfleet

4.98 out of 5 average rating, 101 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.

Condo in Brewster

4.85 out of 5 average rating, 48 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.

A communal pool area features a clear blue pool surrounded by concrete decking. Lounge chairs are arranged neatly on the sides, with greenery visible in the background. A wooden fence encloses the area, providing a private atmosphere.

Condo in Dennis Port

4.91 out of 5 average rating, 112 reviews

The Sea Salt Studio - Steps to the Beach!

Gorgeous studio (Unit #1) only 175 yards from white sand Glendon Road beach. Soak up the sun at the beach, relax by the pool or enjoy a relaxing cocktail on your own private patio. This studio is equipped with a fridge, microwave and gas stove as well as a fully stocked kitchenette and cable/Roku TV. A futon couch offers extra sleeping space, if needed. Outside, enjoy a natural gas grill. Walk or bike to multiple restaurants, ice cream shops and all the amenities Dennis Port has to offer.

The exterior of the two-story home is showcased, featuring a spacious deck with ample seating and a swimming pool in the foreground. A colorful pool float rests on the water, while greenery surrounds the property, enhancing the cozy outdoor space.

Home in East Dennis

4.82 out of 5 average rating, 11 reviews

Family Fun- Games, Pool & HotTub, Dogs ok! Slps 10

Welcome to Sesuit Harbor Hideaway – your perfect Cape Cod getaway! This spacious 4-bedroom, 3-bathroom home offers a relaxing escape, complete with all the amenities you need for an unforgettable vacation. Nestled in a quiet, charming neighborhood, it’s ideal for families, friends, or groups looking to enjoy the best of the Cape. 6min to Cold Storage beach 5min to Sesuit Harbor Café 3min to Dennis Pines Golf Course 3min to Scargo Tower 10 minutes to Mayflower Beach

Home in Brewster

4.98 out of 5 average rating, 40 reviews

Modern Cape, Private Salt Water Pool, Beaches-Golf

Welcome to your perfect Cape Cod vacation! Nestled in the center of the Cape. Min. to 3 golf courses, 5 ocean beaches, lakes, bike trail etc. Vast serene private 1.5 acres adjacent to conservation land. Lighted Private heated salt water pool, Bocce Court, Putting green, corn hole, hammock, outdoor shower etc. Expansive double deck with awning . All essential amenities provided. Spacious Beautiful indoor/outdoor dining/entertaining. Pool heat 05/15 to 10/06

Top guest favorite

A welcoming living area features a comfortable sectional sofa and two wooden armchairs arranged around a circular coffee table. Natural light fills the space, highlighting a large area rug on the hardwood floor. A well-equipped kitchen is visible in the background.

Condo in New Seabury

4.97 out of 5 average rating, 159 reviews

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

Welcome to Your Coastal Getaway at The Mews, New Seabury – Mashpee, MA Tucked inside the beautiful New Seabury Country Club, our cozy Cape-style condo offers the perfect balance of relaxation and adventure on Cape Cod. Enjoy access to a private condo association pool just a 3-minute walk away, and a beach that is 5 min drive or 10 min bike ride or 30 min walk (walk cuts through golf course-ask host for directions).

An inviting living space is highlighted with a grey sofa, modern dining table with four chairs, and bright windows allowing natural light. The kitchen has sleek cabinets and appliances. Below, the scenic Keyes Memorial Beach is shown with soft sand and a sunset. A community pool featuring turquoise water and lounge chairs is also visible.

Apartment in Hyannis Port

4.87 out of 5 average rating, 102 reviews

Cute Cottage Near Beach & Main Street 3BR/3BA (15)

Stay at a charming 3-Bedroom cottage in a beautiful setting within walking distance to Cape Cod's warm sandy beaches and Main Street Hyannis. Captain Gosnold Village is ideally located within a short walk from three of the Cape's best beaches and nestled between picturesque Hyannis Port and the vibrant atmosphere of Hyannis Harbor with its island ferries, sightseeing and fishing charters.

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Popular amenities for Brewster rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Top guest favorite

The outdoor pool area features a clear blue pool surrounded by a concrete patio. Sun loungers and white Adirondack chairs are positioned nearby. A shaded cabana provides relief from the sun, complemented by lush greenery in the background, enhancing the serene atmosphere.

Home in North Eastham

5 out of 5 average rating, 19 reviews

Heated Pool, Game Room, Projector Room, Private

An inground pool is surrounded by lush greenery, featuring vibrant flowering plants and bushes. The clear blue water reflects the sky, while stairs lead into the pool. A natural stone patio borders the pool area, enhancing the outdoor space.

Home in Orleans

4.91 out of 5 average rating, 33 reviews

5-bedroom Cape with a pool and yard games.

A serene backyard setting features a private pool surrounded by a spacious patio. A sunbathing chair and a BBQ grill are positioned nearby, with a house showcasing large windows that invite natural light. Lush greenery frames the area, providing a sense of tranquility.

4.72 out of 5 average rating, 39 reviews

House on Cape Cod with pool close to beach

Home in Dennis Port

4.93 out of 5 average rating, 15 reviews

Sauna, Hot Tub, Walk to Beach -Seaglass Cottage

The exterior showcases a contemporary home with a blend of stone and siding elements. Solar panels are visible on the roof, and a circular driveway leads to a welcoming entrance with double doors. Surrounding greenery enhances the property’s serene setting.

Home in Sagamore

4.96 out of 5 average rating, 23 reviews

XL Cape Retreat - Pool - Hot Tub - 5min to Beach!

An outdoor area showcases a heated pool surrounded by lounge chairs and a shaded seating arrangement. The back of a large two-story home is visible, with multiple windows indicating spacious interiors. Green trees line the background, adding a natural element to the setting.

Home in Plymouth

4.88 out of 5 average rating, 25 reviews

Mansion with Heated Pool Near Ocean

A heated saltwater pool glistens under the sun, surrounded by a spacious paver patio. The fenced backyard provides privacy, while a light-colored house with a deck offers a welcoming ambiance. Lush trees stand in the background, enhancing the serene outdoor space.

Home in Barnstable

4.82 out of 5 average rating, 17 reviews

Centerville Oasis, Heated Saltwater Pool!

A spacious backyard is surrounded by trees, featuring a circular above-ground pool. Nearby, a hammock is hung between two trees. Several white lounge chairs are arranged on the grass, providing a relaxing spot in the sun.

Home in Mashpee

4.85 out of 5 average rating, 65 reviews

Sunny Cape w/Private Pool, Steps to Private Lake

Condo rentals with a pool

A spacious sleeping area features a large bed with neutral bedding and colorful accent pillows. A TV is mounted on the wall. Natural light filters through a sliding glass door, which opens to an outdoor area with a small table and chairs.

Condo in Dennis Port

4.82 out of 5 average rating, 74 reviews

Cozy Studio Just Steps Away From the Beach!

Top guest favorite

A clean outdoor pool is framed by a spacious concrete deck with lounge chairs positioned nearby. Lush greenery and landscaped areas are visible around the pool, contributing to a serene environment. The sky above is clear, enhancing the bright atmosphere of the setting.

Condo in West Dennis

4.93 out of 5 average rating, 44 reviews

1BR 2nd Floor Condo with pool

A clear blue pool is surrounded by lounge chairs, offering a refreshing spot for relaxation. The two-story building in the background features balconies with umbrellas and well-maintained landscaping, creating a serene atmosphere for guests.

Condo in West Dennis

4.85 out of 5 average rating, 60 reviews

Hidden Hideaway

An outdoor saltwater pool is framed by comfortable lounge chairs under clear blue skies. Lush greenery surrounds the pool area, providing a serene atmosphere for relaxation and enjoyment. A set of steps leads into the inviting water.

Condo in Mashpee

5 out of 5 average rating, 3 reviews

1BR Condo w/ Balcony in Mashpee, MA

An indoor pool area is illuminated by large windows that provide natural light. White lounging chairs are arranged around the pool, and potted plants add a touch of greenery. The clear water reflects the inviting setting, creating a serene atmosphere.

Condo in Teaticket

4.63 out of 5 average rating, 8 reviews

InnSeason Resorts Surfside

A crystal-clear pool is framed by a deck lined with blue lounge chairs. The setting includes landscaped greenery and trees, with two-story buildings in the background providing serene surroundings. The clear blue sky enhances the tranquil atmosphere of this communal outdoor space.

Condo in West Dennis

4.86 out of 5 average rating, 57 reviews

Mid Cape Cod, 3 Season Haven by Bass River

Condo in Dennis Port

4.5 out of 5 average rating, 12 reviews

A Beautiful Es-Cape

Top guest favorite

Condo in West Dennis

4.97 out of 5 average rating, 65 reviews

6 Min to Beach - Pool - Private Balcony - Central

Other vacation rentals with a pool

A spacious deck features a wooden dining table with matching chairs, overlooking a private heated pool and serene water views. Lush greenery surrounds the area, while a private dock is visible along the shoreline.

Home in New Seabury

5 out of 5 average rating, 7 reviews

Waterfront Home w/ Dock, Heated Pool, Kayaks & A/C

A sunny outdoor area is showcased, featuring a private heated pool surrounded by lounge chairs. Large blue umbrellas provide shade next to the pool, while decorative landscaping and a wooden playset are visible in the background. The space invites relaxation and comfort.

Home in Harwich

4.89 out of 5 average rating, 18 reviews

Cape Cod Heated Pool Putt-Putt Golf Speak Easy Gam

A private pool area features a rectangular swimming pool surrounded by a concrete deck. Several blue lounge chairs are positioned along the perimeter. Lush greenery and trees provide secluded shade, while a gravel pathway leads to the pool area, enhancing the outdoor experience.

Apartment in West Dennis

4.95 out of 5 average rating, 22 reviews

Town House for Cape Cod fun, by Bass River.

A clear blue pool is surrounded by a spacious patio area. Several lounge chairs are positioned nearby under the sun. The pool is accessed via a white gated area, with a clean, inviting atmosphere represented by the well-maintained surroundings.

Condo in Dennis Port

4.88 out of 5 average rating, 74 reviews

Stylish & Modern Studio Condo - Steps to the Beach

The exterior of a blue townhome is shown, featuring a red door and white trim. Lush green landscaping surrounds the entrance, with a well-kept lawn and mature trees in the background. A paved pathway leads up to the front door.

Townhouse in Brewster

4.86 out of 5 average rating, 21 reviews

Coastal Oasis: Brewster-Cape Cod

A view from the deck reveals a well-maintained pool area surrounded by lounge chairs and umbrellas. Adjacent to the pool is a tennis court, framed by greenery, providing a serene backdrop. The water sparkles under a clear blue sky, inviting relaxation.

Home in East Falmouth

4.95 out of 5 average rating, 55 reviews

Dog Friendly Cape Oasis | Pool+Beach |Tennis Court

The living area features a white fireplace and hardwood flooring. Two blue sofas are positioned around a white coffee table, while a round dining table sits nearby. A mirror and nautical-themed decor are visible against a blue accent wall.

Cottage in South Yarmouth

4.96 out of 5 average rating, 76 reviews

Cottage near beach with pool and breakfast

A covered walkway leads to a grassy area with well-maintained landscaping. Lounge chairs are arranged around a heated pool, with ocean views visible beyond a fenced area. The building's exterior features a wooden overhang, providing shade along the path.

Apartment in Dennis Port

4.78 out of 5 average rating, 9 reviews

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Quick stats about vacation rentals with a pool in Brewster

Total rentals
60 properties
Nightly prices starting at
ﺩ.ﺇ698 before taxes and fees
Total number of reviews
1.6K reviews
Family-friendly rentals
50 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace

Destinations to explore