
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 $200 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.

“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.
FamilyLocationPool

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.
ValueLocationHot tub

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.
FamilyLocationIndoor spaces

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
ValueFamilyKitchen

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.
FamilyLocationParking

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 6/20-9/15/26. The reviews tell all!
FamilyValueView

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.
LocationFamilyCleanliness

"Cape Escape" luxury home w/pool & beach access.
Welcome to the Cape Escape! Enjoy views of Spectacle Pond from the 70 ft. deck of this recently renovated 5 bed/3 bath spacious home meeting all your needs! Relax by the in-ground pool in the private enclosed yard. Enjoy nights around the fire-pit. Directly across the driveway you can enjoy kayaking, sunbathing & swimming at the neighborhood beach. Within 6 miles of the home you will find the historic Sandwich boardwalk, Ocean beaches, Cape Cod Canal and more! Perfect for family gatherings!
FamilyLocationView

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!
LocationFamilyParking

The Holly Cottage
Welcome to Centerville, enjoy this fully equipped 1 bedroom 1 bath home with an easy walk or ride to just about everything. Enjoy the nearby ocean and beaches, or take a ride downtown to Main Street for dining and entertainment. Only a short distance to the ferries for a day trip to the islands and you can be back in time to catch a concert at the Melody Tent. Enjoy your days by the pool and your evenings grilling out on the large deck or chatting with the koi fish.
LocationFamilyNearby

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.
LocationFamilyOutdoor spaces

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 + 2 twins). Includes an equipped kitchen, in-unit laundry, and a covered patio with fairway views. Near Brewster’s beautiful beaches, shops, and dining.
FamilyLocationQuiet
Popular amenities for Brewster rentals with a pool
House rentals with a pool

5-bedroom Cape with a pool and yard games.
LocationFamilyNearby

House on Cape Cod with pool close to beach
LocationValueKitchen

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

ShoestringBayHouse, waterfront & pool in Cotuit
FamilyLocationQuiet

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

Game Room- Movie Projector Room- Fire Pit
FamilyLocationHospitality

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

Jolly Captain Lighthouse
LocationFamilyComfort
Condo rentals with a pool

Cozy Studio Just Steps Away From the Beach!
FamilyValuePool

1BR 2nd Floor Condo with pool
ValueLocationPool

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

Resort Pools & Golf Views · Walk to Bay Beaches
ValueLocationGrill

Lovely townhouse at Cape Cod's Ocean Edge
FamilyLocationOutdoor spaces

Vacation Bliss at Ocean Edge Resort
Getting aroundAccessHospitality

Hidden Hideaway
LocationValueOutdoor spaces

Mary's Cape Escape
FamilyValueLayout
Other vacation rentals with a pool

In-Ground Pool Oasis | 5 Min to Cape Cod Beaches!
FamilyValueOutdoor spaces

Cape Cod multi-structure family compound with Pool
FamilyLocationIndoor spaces

Breezy Pool Retreat Near Mayflower Beach
FamilyLocationAccess

Luxury Historic Estate with Expansive Grounds
LocationFamilyBeach

Coastal Charm New Seabury: 5BRs with Private Pool
FamilyLocationQuiet

Luxury retreat, in-ground pool, 10-person hot tub
LocationFamilyCleanliness

King Bed Suite (Pet Friendly) in a Great Location
LocationValueHospitality

Cottage at the Escape Inn
ValueFamilyAccuracy
When is the best time to visit Brewster?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $512 | $474 | $474 | $314 | $367 | $383 | $558 | $652 | $426 | $398 | $295 | $499 |
| Avg. temp | 32°F | 32°F | 37°F | 45°F | 54°F | 63°F | 70°F | 69°F | 64°F | 55°F | 46°F | 38°F |
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