Become a host

Vacation rentals with a pool in Brewster

Find and book unique homes with a pool on Airbnb

Quick stats about vacation rentals with a pool in Brewster

  • Total vacation rentals

    Explore 60 vacation rentals in Brewster

  • Nightly prices starting at

    Brewster vacation rentals start at G$41,840 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,710 verified reviews to help you choose

  • Family-friendly vacation rentals

    50 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    60 of Brewster vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Brewster rentals

  • 4.8 Average rating

    Brewster stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated rentals with a pool in Brewster

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

1 of 1 pages1 / 1
Top guest favorite
Guest suite in Centerville

“The Hideaway”Private Guest Suite/Pool/Beach Pass

Enjoy a bit of Cape Cod in a friendly and walkable neighborhood of lush green trees , flower gardens, and a walking trail. Less than 1 mile from Centerville's shops and restaurants. Less than 2 miles from Craigville Beach and its beachside walk up shanty’s for lunch. A small beach on Lake Wequaquet is only 2 miles down the road . Main street Hyannis, a walkable downtown with many shops and restaurants is a quick 10-minute drive. Ocean marinas, and ferries to the islands, are a 15 minute drive.

4.99 out of 5 average rating, 105 reviews
Top guest favorite
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

Resort Home, Heated Pool, Putting Green, Game Room

Escape to our serene, spacious home, a private oasis perfect for families & groups! This stylish retreat features a heated pool, putting green, fire pit, and a full game room with a pool table, poker lounge, and arcade games. Nestled in a peaceful, wooded neighborhood with nearby lake access, it's the ultimate blend of relaxation and entertainment. Enjoy a seamless self-check-in experience with an on-site EV charger. You will receive a four-digit access code after you agree and complete the hous

4.93 out of 5 average rating, 29 reviews
Top guest favorite
An open living area features large glass doors that provide views of the golf course. A comfortable seating arrangement includes a recliner and a sectional sofa. A spiral staircase leads to the loft above, and a mounted television is positioned above a modern fireplace.
Condo in Brewster

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.

5.0 out of 5 average rating, 105 reviews
Top guest favorite
The balcony offers a view of the lush golf course, framed by trees and natural landscape. A round table with two high stools sits center stage, accompanied by a candle, creating a peaceful outdoor setting for relaxation.
Condo in Brewster

Ocean Edge Resort-Pool Access-CentralAC-2 bdr/2bth

Modern 2nd floor 2 bed/2 full bath Ocean Edge condo located in the heart of Brewster with balcony overlooking the resort golf course. Access to OE resort amenities (additional fees apply). Easy access to Cape Cod Rail Trail. Scenic route 6A offers arts & crafts galleries, coffee places 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. 15 minute walk to Ellis Landing Beach, great sunsets! Central A/C and heat

5.0 out of 5 average rating, 113 reviews
Top guest favorite
Home in Brewster

Modern Cape, Private Heated Pool, Beach, Golf

Welcome to your perfect vacation/reunion in the center of the Cape. Min. to 3 golf courses, 5 ocean beaches, lakes, park, trails. Bright modern quality home, AC, enjoyable year-round. Vast serene private 1.5 acres adjacent to conservation land. Pool heated Memorial day weekend- last Sunday of Sept. Bocce Court, Putting green, Corn hole, Hammock, Outdoor shower, AC. Expansive double deck with awning. Beautiful indoor/outdoor dining/entertaining. All essentials provided. 7+ free parking.

4.98 out of 5 average rating, 54 reviews
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

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.

4.96 out of 5 average rating, 99 reviews
Top guest favorite
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

Sea Salt Studio - Steps to Glendon Rd Beach

Funky studio (Unit #1) only 175 yards from a white sand beach on Nantucket Sound. 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.

4.93 out of 5 average rating, 134 reviews
Guest favorite
Condo in Brewster

Resort Pools & Golf Views · Walk to Bay Beaches

Spend your Cape Cod days at the beach and evenings on your private patio overlooking the golf course at Ocean Edge Resort. This spacious, freshly renovated 2-bed, 2-bath condo sleeps 6 and is steps from the CC Rail Trail, Blueberry Pond and a short walk to Ellis Landing Beach — with 10 bay beaches, shopping and restaurants nearby. Optional resort day passes unlock pools, fitness center, kids' activities, free shuttle, and rentals (bikes, kayaks, tennis & more). Perfect for families or friends!

4.87 out of 5 average rating, 77 reviews
Top guest favorite
Apartment in Brewster

Two Bedroom Condo in Ocean Edge Resort

Experience the perfect blend of relaxation and recreation in this updated 2-bed, 2-bath condo at Ocean Edge Resort, Brewster. Near the Arbor pool and Linx Golf Club, it’s an ideal hub. The primary suite features a queen bed, golf views, and a renovated ensuite. The second bedroom features an oversized bunk (full + twin beds) AND a pull out trundle bed. Includes an equipped kitchen, in-unit laundry, and a covered patio with fairway views. Near Brewster’s beautiful beaches, shops, and dining.

5.0 out of 5 average rating, 11 reviews
Top guest favorite
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

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!

5.0 out of 5 average rating, 37 reviews
Guest favorite
Home in East Dennis

Charming Cape Escape with Pool, Hot Tub & Fire Pit

Welcome to Searside Retreat, your ultimate Cape Cod escape in South Dennis! This charming home offers a private pool, open layout, and modern comforts just minutes from top beaches, restaurants, and shops. Relax in a quiet neighborhood in the heart of the Cape. Mayflower Beach - 10min Chapin Beach - 6 min Cape Cod Rail Trail – 10min The Marshside Restaurant – 2min Sesuit Harbor Cafe - 5 min Scargo Cafe - 5 min Smugglers Ice Cream - 5 min Learn more below!

5.0 out of 5 average rating, 11 reviews
Top guest favorite
Condo in New Seabury

New Seabury Cape Condo | Pool & Beach Escape

Top 5% of Air Bnbs! Welcome to your coastal getaway at The Mews in New Seabury, Mashpee—a refined Cape-style condo tucked within an intimate golf course community. This exclusive enclave of just 15 residences offers a peaceful, private escape with access to a shared association pool reserved solely for residents. Enjoy nearby beaches like South Cape Beach State Park and Mashpee Town Beach, both just minutes away, for the perfect Cape Cod retreat.

4.97 out of 5 average rating, 183 reviews

Popular amenities for Brewster rentals with a pool

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

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.
Home in Cotuit

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

4.96 out of 5 average rating, 146 reviews
Guest favorite
Home in West Yarmouth

Coastal Luxury Oasis - Ag2 Luxury Home

4.83 out of 5 average rating, 6 reviews
Guest favorite
The lighthouse features a round white structure topped with a lantern room. A spacious deck wraps around the building, accompanied by a well-maintained lawn and a decorative pumpkin. American flags are displayed, and the surrounding area includes additional nearby structures and views of the water.
Home in West Dennis

Jolly Captain Lighthouse

4.85 out of 5 average rating, 26 reviews
Top guest favorite
A spacious backyard is featured, highlighting a refreshing oval pool surrounded by a textured patio. Lounge chairs are positioned for relaxation under the sun. Lush greenery and trees provide a natural border, while a well-kept lawn enhances the inviting outdoor space.
Home in Chatham

Pool. Hot Tub. Game Room. Walk to Beach. Luxury!

5.0 out of 5 average rating, 15 reviews
Guest favorite
A spacious outdoor area is highlighted by a seasonal heated pool surrounded by a wooden deck. Multiple blue lounge chairs are arranged around the pool, and a fire pit table is situated at the center. A large checkers board and garden beds add to the inviting atmosphere.
Home in Yarmouth Port

Winslow Acres [heated] Pool Escape; pool May-Oct

4.93 out of 5 average rating, 54 reviews
Superhost
Home in Yarmouth

Heated Pool | 5 Min Walk to Beach | Dog-Friendly

5.0 out of 5 average rating, 7 reviews
Guest favorite
Home in Chatham

Walk 2Beach, Pool, Hot Tub, GameRoom, PetsOK

4.92 out of 5 average rating, 51 reviews
Guest favorite
An aerial view of a spacious property featuring a uniquely shaped heated saltwater pool surrounded by a stone patio. A large deck is positioned next to the pool, with several lounge chairs arranged nearby and greenery framing the area.
Home in New Seabury

Coastal Charm New Seabury: 5BRs with Private Pool

4.94 out of 5 average rating, 53 reviews

Condo rentals with a pool

Guest favorite
Condo in West Dennis

Steps from Bass River Marina · Private Balcony

4.96 out of 5 average rating, 83 reviews
Top guest favorite
A light-filled living area features a cozy sofa layered with a soft throw, accompanied by a stylish coffee table. The calming wall art depicts ocean waves, while lamps provide additional lighting. A door leads outside, and a chair adds a pop of color.
Condo in West Dennis

1BR 2nd Floor Condo with pool

4.92 out of 5 average rating, 51 reviews
Guest favorite
A wooden sign is displayed on a light-colored wall, featuring the phrase 'Heaven is a little closer by the Beach' in white lettering on a teal background. The sign is framed in a rustic white border, enhancing its coastal charm.
Condo in West Dennis

Hidden Hideaway

4.88 out of 5 average rating, 72 reviews
Superhost
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

Mid Cape Cod, 3 Season Haven by Bass River

4.86 out of 5 average rating, 65 reviews
Guest favorite
A view of Bass River is presented, featuring a calm waterway with several boats docked at a marina. Well-maintained lawns and planted shrubs frame the scene, while a flagpole with an American flag stands in the foreground under a clear blue sky.
Condo in West Dennis

Carolyn's Bass River Condo

4.9 out of 5 average rating, 30 reviews
Superhost
The exterior of a multi-story building showcases a charming design with cedar shingles and large windows. A covered porch with seating is visible at the entrance, while light clouds drift across a blue sky above.
Condo in Dennis Port

Cape Cod 1BR Condo on lovely Ocean Front Resort

5.0 out of 5 average rating, 4 reviewsA spacious living area features light yellow walls, a glass-top coffee table, and a patterned area rug. A dining table with seating for six is positioned nearby, with a flat-screen television visible on a stand. Natural light fills the space through multiple entrances.
Condo in Brewster

Brewster Roost, In Villages of Ocean Edge Resort

4.91 out of 5 average rating, 104 reviews
Guest favorite
A two-story condo is shown surrounded by lush green trees and shrubs. The exterior features a light gray facade with white trim, and large windows are visible on both levels, allowing natural light to fill the interior. A well-maintained pathway leads to the entrance.
Condo in Brewster

Lovely townhouse at Cape Cod's Ocean Edge

5.0 out of 5 average rating, 36 reviews

Other vacation rentals with a pool

Top guest favorite
Cottage in Yarmouth

Cottage at the Escape Inn

4.97 out of 5 average rating, 39 reviews
Guest favorite
A charming cottage exterior is showcased, featuring natural wood shingles and red shutters. A bright orange door provides a welcoming entrance. Lush green leaves frame the image, highlighting the serene surroundings of the property against a clear sky.
Cottage in Wellfleet

Wellfleet~Beautiful One Day Perfect The Next

4.87 out of 5 average rating, 67 reviews
Guest favorite
Apartment in Dennis Port

Deluxe Double Room | Full Studio w/ Kitchenette

4.91 out of 5 average rating, 11 reviews
Guest favorite
A modern kitchen is displayed, featuring stainless steel appliances, sleek cabinetry, and contemporary lighting along the countertops. A dining table with high-backed stools is positioned near the kitchen, with a decorative vase of yellow flowers adding a touch of color.
Apartment in Dennis

Fall Into Cape Cod | Cape Storia d'Amore

4.9 out of 5 average rating, 70 reviews
Guest favorite
Home in North Eastham

Game Room- Movie Projector Room- Fire Pit

5.0 out of 5 average rating, 12 reviews
Top guest favorite
A refreshing swimming pool is surrounded by a concrete deck, featuring several lounge chairs positioned along one side. Umbrellas provide shade near the pool's edge, and a fenced yard is adorned with greenery, creating a serene outdoor setting.
Home in Barnstable

Beach Pass Included! Brand New Spa! Central AC!

4.97 out of 5 average rating, 32 reviews
Superhost
Apartment in Dennis Port

King Bed Suite (Pet Friendly) in a Great Location

4.82 out of 5 average rating, 39 reviews
Top guest favorite
A spacious living area showcases an inviting arrangement of black leather sofas surrounding a dark wooden coffee table. A decorative area rug adds warmth to the room, while large windows allow natural light to fill the space. A stone fireplace is positioned against the far wall.
Home in Sandwich

Large Home Heated Swimming Pool Private Beach

4.95 out of 5 average rating, 92 reviews

When is the best time to visit Brewster?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$107,110 GYDG$99,160 GYDG$99,160 GYDG$65,689 GYDG$76,776 GYDG$80,123 GYDG$116,733 GYDG$136,398 GYDG$89,119 GYDG$83,261 GYDG$61,714 GYDG$104,390 GYD
Avg. temp0°C0°C3°C7°C12°C17°C21°C21°C18°C13°C8°C3°C

Destinations to explore