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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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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

4.87 out of 5 average rating, 47 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

The living area features a light-colored sofa paired with matching armchairs. A small table holds fresh flowers. Soft lighting from lamps creates a comfortable environment. Large sliding doors provide natural light and open to an outdoor patio with a dining set.

Condo in Brewster

4.97 out of 5 average rating, 76 reviews

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

Condo in Brewster

5 out of 5 average rating, 78 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

The expansive pool, surrounded by a landscaped yard, features a vibrant blue surface reflecting the clear sky. Comfortable lounge chairs are positioned alongside, inviting relaxation. A floating inflatable adds a playful touch to the tranquil setting.

4.95 out of 5 average rating, 121 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, 184 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!

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, 108 reviews

The Sea Salt Studio - Steps to the Beach!

Gorgeous studio 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, Bluetooth speaker, and 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.

Condo in Brewster

4.93 out of 5 average rating, 58 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.

A spacious heated saltwater pool is surrounded by a large deck featuring colorful lounge chairs and an umbrella. The attractive two-story house stands in the background, framed by lush greenery and trees, creating a peaceful outdoor setting.

Home in Brewster

4.97 out of 5 average rating, 36 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 . Chef’s kitchen & all essential amenities provided. Spacious Beautiful indoor/outdoor dining/entertaining. Pool heat 05/15 to 10/01

Home in Plymouth

4.9 out of 5 average rating, 128 reviews

Seaview Summit | Ocean Views, Indoor Pool, Beach

Welcome to Seaview Summit House, where you can enjoy breathtaking panoramic ocean views, take a dip in our heated swimming pool, and take a short walk to the beach. Our spacious and beautifully decorated home features a large living area with comfortable seating, a fully equipped kitchen with all the essentials, and a dining area that seats everyone. You'll have plenty of room to spread out and enjoy your time together, whether you're lounging inside or soaking up the sun outside.

An aerial view of a spacious property featuring a private pool, surrounded by lush greenery and well-maintained gardens. The house showcases an expansive layout with multiple outdoor seating areas and pathways leading to vibrant landscaping.

Home in Brewster

5 out of 5 average rating, 13 reviews

Cape Cod Oasis: pool, hot tub, firepit & grill!

Over 4500 sqft of living space in the heart of Cape Cod, with an inviting pool, a brand new hot tub, magnificent garden and expansive outdoor living space big enough to fit your entire party. Welcome to your own private resort! This beautiful custom-built center entrance colonial has room to roam, both inside and out. 5 beds, 5 baths, eco pool, The building is surrounded by lush landscape and tastefully decorated. Fully equipped chef's kitchen. Short drive to the beach!

Bright and airy living space is highlighted by a spiral staircase leading to an open loft. A plush light grey sofa faces a coffee table on a woven area rug, while a dining table and chairs are visible in the background. Modern kitchen cabinetry offers a sleek contrast.

Apartment in Brewster

5 out of 5 average rating, 22 reviews

Townhouse at Ocean Edge 2B/2B + Loft

Experience resort-style living at its finest! Tucked away just a 10-minute drive to the beach, this delightful townhouse offers the perfect blend of comfort and convenience. With two bedrooms, two baths, and an additional cozy loft space, there's ample room for relaxation. Enjoy lounging on the patio, take a refreshing dip in one of the resort pools (for an additional fee paid directly to Ocean Edge) or head to the beach for some sun and surf. Your ultimate getaway awaits!

A private deck is showcased with outdoor furniture, including a round table and chairs. A colorful striped umbrella provides shade, while surrounding greenery and flowers add a natural touch. The deck is well-lit by sunlight, creating a warm and inviting space.

Apartment in Hyannis Port

4.88 out of 5 average rating, 130 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. Keurig, and kettle.

Vacation rentals for every style

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Villas

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Cottages

Quaint homes, peaceful surroundings

Popular amenities for Brewster rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

A private backyard features a large swimming pool surrounded by a patio with stone paving. Lush greenery and low shrubs border the area, while a wooden table and chairs are positioned nearby. The house is visible in the background, framed by trees.

Home in Mashpee

4.9 out of 5 average rating, 21 reviews

Beautiful Mashpee Home with Pool

Top guest favorite

Home in Sandwich

4.99 out of 5 average rating, 85 reviews

"Cape Escape" luxury home w/pool & beach access.

Top guest favorite

A saltwater pool is set within a stone patio area, surrounded by lush greenery. Lounge chairs and a shaded table with a red umbrella offer comfortable seating options. The serene view of Morey Pond is visible beyond the pool, framed by trees under a clear blue sky.

Home in Plymouth

4.97 out of 5 average rating, 62 reviews

Our families slice of heaven

An expansive outdoor pool is surrounded by a spacious deck with various lounge chairs and umbrellas for shade. Lush greenery and landscaped areas provide a serene ambiance, while the boundary features a white fence, enhancing privacy and relaxation.

5 out of 5 average rating, 12 reviews

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

An outdoor pool area showcases a heated inground pool with clear water, surrounded by a wooden deck. Sun loungers are placed nearby, and patio umbrellas provide shade. Lush greenery and trees line the background, offering a serene environment. A beach ball floats in the water.

Home in New Seabury

5 out of 5 average rating, 22 reviews

Exclusive New Seabury Home w/ Heated Pool ⛳️🏖🦞☀️🐠

A spacious, inviting pool is surrounded by a stone patio and lush greenery. Several lounge chairs are positioned around the pool, offering relaxation spots. The clear blue water reflects the sunlight, while a gentle slope leads to a grassy area beyond.

4.92 out of 5 average rating, 53 reviews

Cape Cod Lakefront Home

The exterior of the home is presented with natural wood siding, complemented by green shutters. Solar panels are mounted on the roof. A welcoming front porch leads to the main entrance, while a garage is visible to the left amidst well-maintained landscaping.

Home in Harwich

4.86 out of 5 average rating, 21 reviews

4 BD slice of Harwich Heaven

Top guest favorite

An in-ground pool is surrounded by a spacious patio, featuring several blue lounge chairs. Lush greenery frames the area, with a clear blue sky overhead. The pool’s water reflects the sunlight, creating a refreshing ambiance for relaxation and entertainment.

Home in Hyannis Port

5 out of 5 average rating, 18 reviews

Home in Hyannis Port

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

4.81 out of 5 average rating, 67 reviews

Cozy Studio Just Steps Away From the Beach!

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

4.92 out of 5 average rating, 37 reviews

1BR 2nd Floor Condo with pool

A charming, single-story building is visible from the road, featuring a gray exterior and a white picket fence that encloses a well-kept yard. Leafy trees provide shade, and clear blue skies are overhead, creating a welcoming ambiance for guests.

Condo in Dennis Port

4.83 out of 5 average rating, 82 reviews

Comfy Cape Escape! Spacious, Cozy, Close to Beach!

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, 54 reviews

Hidden Hideaway

A serene pool area is visible, featuring clear blue water under a sunny sky. Poolside loungers are arranged for relaxation, while the two-story condo building with balconies lines the background. Lush greenery and trees enhance the outdoor space.

Condo in West Dennis

4.96 out of 5 average rating, 54 reviews

Mary's Cape Escape

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

4.85 out of 5 average rating, 52 reviews

Mid Cape Cod, 3 Season Haven by Bass River

A serene beach scene features footprints in sandy shorelines under a colorful sunset. An inviting hot tub is showcased with bubbling water next to a sparkling outdoor pool. A cozy bedroom includes a spacious bed with light blue walls, accompanied by a small dining table and a stylish fireplace.

Condo in Dennis Port

4.83 out of 5 average rating, 6 reviews

Oceanfront 1-Bedroom Condo w/ Balcony Views

Condo in Dennis Port

4.78 out of 5 average rating, 9 reviews

A Beautiful Es-Cape

Other vacation rentals with a pool

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

4.78 out of 5 average rating, 23 reviews

Beachside Condo with Balcony - Oceanside Condos

Top guest favorite

An outdoor area features a spacious table with four chairs under a large yellow umbrella, providing shade. Nearby, a private hot tub is tucked away among trees, while a small white side table and a blue adirondack chair complete the relaxing ambiance.

Home in Dennis Port

5 out of 5 average rating, 11 reviews

Sauna, Hot Tub, Walk to Beach -Seaglass Cottage

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

4.94 out of 5 average rating, 17 reviews

Town House for Cape Cod fun, by Bass River.

Top guest favorite

The swimming pool is surrounded by a private wooden fence, with vibrant blue water reflecting the clear sky. Floating pool toys, including a unicorn and a large duck, are visible. The backdrop features a charming house and lush greenery, enhancing the secluded atmosphere.

Camper/RV in Wellfleet

5 out of 5 average rating, 34 reviews

Seasonal 27’ Retro Glamping Steps From Bike Trail

A spacious living area is highlighted by a large fireplace and a sleek television mounted above it. Comfortable seating arranged around a central coffee table invites relaxation. A leafy plant adds a touch of greenery, while natural light fills the space through nearby windows.

Home in West Yarmouth

5 out of 5 average rating, 8 reviews

Cape Cod Family Vacation

An A-Frame structure is set against a backdrop of trees, with expansive glass doors facing a private pool. The pool area features a stone deck, several lounge chairs, and a shaded seating area under a canopy. The fenced yard offers a spacious and inviting environment.

Farm stay in Brewster

4.94 out of 5 average rating, 16 reviews

Modern A-Frame Farm Stay! One bedroom+ loft

A bright bedroom features a spacious bed with striped bedding and decorative pillows. A cozy throw blanket is placed at the foot of the bed. Natural light filters through the two windows, and a floor lamp adds additional lighting. A framed art piece is mounted on the wall.

Home in Sandwich

4.89 out of 5 average rating, 9 reviews

Coastal Retreat in Sandwich -Pool Access, Dogs OK!

A serene beach scene at sunset features vibrant hues of orange, pink, and purple in the sky, reflecting on the gently rippling water. Soft sandy shore is visible in the foreground, with small clumps of seaweed scattered along the sand.

Townhouse in Brewster

5 out of 5 average rating, 7 reviews

Ocean Edge townhouse w/ access to resort amenities

Quick stats about vacation rentals with a pool in Brewster

Total rentals
60 properties
Nightly prices starting at
G$39,447 GYD 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