
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 $278 CAD 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 and kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
60 of Brewster vacation rentals include wifi 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.

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.

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.

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

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.

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!

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.

"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!

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!

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.

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.

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.

Ocean Edge Townhouse/Pool Access
End unit townhouse located in heart of OE Villages with private patio, A/C & W/D. There’s no better way to experience all that Brewster has to offer than taking your family to stay at the Ocean Edge Resort. Just minutes off the property you will find yourself at the beach, on the golf course, or at one of the many excellent local restaurants. Unit has pool & fitness access for additional fees.
Popular amenities for Brewster rentals with a pool
House rentals with a pool

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

5-bedroom Cape with a pool and yard games.

House on Cape Cod with pool close to beach

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

ShoestringBayHouse, waterfront & pool in Cotuit

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

Game Room- Movie Projector Room- Fire Pit

Winslow Acres [heated] Pool Escape; pool May-Oct
Condo rentals with a pool

Cape Cod 1BR Condo on lovely Ocean Front Resort

Cozy Studio Just Steps Away From the Beach!

1BR 2nd Floor Condo with pool

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

Lovely townhouse at Cape Cod's Ocean Edge

Vacation Bliss at Ocean Edge Resort

Hidden Hideaway

Mary's Cape Escape
Other vacation rentals with a pool

Renovated Cape Oasis W/ New Pool and Game Room!

Pet Friendly Near Mayflower Beach | Pool & Hot Tub

Town House for Cape Cod fun, by Bass River.

Breezy Pool Retreat Near Mayflower Beach

King Bed Suite (Pet Friendly) in a great location

Coastal Charm New Seabury: 5BRs with Private Pool

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

Cottage at the Escape Inn
When is the best time to visit Brewster?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $713 CAD | $660 CAD | $660 CAD | $437 CAD | $511 CAD | $533 CAD | $777 CAD | $908 CAD | $593 CAD | $554 CAD | $411 CAD | $695 CAD |
| Avg. temp | 0 °C | 0 °C | 3 °C | 7 °C | 12 °C | 17 °C | 21 °C | 21 °C | 18 °C | 13 °C | 8 °C | 3 °C |
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