
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 R 3,239 ZAR 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.

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

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/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.

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.

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.

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!

"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!

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.

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.

Ocean Edge Cape House with Beach, Pool, and AC
Your dream Cape Cod getaway awaits! This classic Cape Cod cottage is nestled in the heart of Brewster, offering a perfect blend of comfort, relaxation, and outdoor adventure. With access to a private beach, resort-style amenities, and iconic local attractions, this is the ultimate retreat for families, couples, or groups looking to experience the best of the Cape.
Popular amenities for Brewster rentals with a pool
House rentals with a pool

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

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

5-bedroom Cape with a pool and yard games.

ShoestringBayHouse, waterfront & pool in Cotuit

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

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

Charming Cape Escape with Pool, Hot Tub & Fire Pit

Waterfront Bass River Jolly Captain
Condo rentals with a pool

New Seabury Cape Condo | Pool & Beach Escape

Steps from Bass River Marina · Private Balcony

Carolyn's Bass River Condo

Mid Cape Cod, 3 Season Haven by Bass River

Hidden Hideaway

Mary's Cape Escape

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

Cozy Studio Just Steps Away From the Beach!
Other vacation rentals with a pool

Wellfleet~Beautiful One Day Perfect The Next

Dennis Deluxe King Room | Full Studio w/ Kitchenet

Cottage at the Escape Inn

Breezy Pool Retreat Near Mayflower Beach

The Captain's Quarters Suite - #10

Beachwalk cozy studio with pool!

King Bed Suite (Pet Friendly) in a great location

Game Room- Movie Projector Room- Fire Pit
When is the best time to visit Brewster?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | R 8,291 ZAR | R 7,676 ZAR | R 7,676 ZAR | R 5,085 ZAR | R 5,943 ZAR | R 6,202 ZAR | R 9,036 ZAR | R 10,558 ZAR | R 6,898 ZAR | R 6,445 ZAR | R 4,777 ZAR | R 8,080 ZAR |
| 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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- Cape Cod
- Mayflower Beach
- West Dennis Beach
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