Holiday 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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Guest favourite

Condo in Brewster

4.88 out of 5 average rating, 48 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 favourite

Condo in Brewster

4.97 out of 5 average rating, 79 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.

Guest favourite

Condo in Brewster

5 out of 5 average rating, 81 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.

Guest favourite

Condo in Brewster

4.97 out of 5 average rating, 185 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!

Superhost

Condo in Brewster

4.85 out of 5 average rating, 47 reviews

Golf Course Views and Pools

Enjoy your Cape Cod vacation in Brewster, MA by staying in a cozy and bright condo unit. The unit itself is overlooking hole #12 on a beautiful golf course, owned by well-known Ocean Edge Resort. Lined with plenty of trees there is privacy and quietness, perfect for sitting on the outdoor balcony underneath the stars with a relaxing glass of wine. Part of a country club, you have access to multiple indoor/outdoor swimming pools, gym, saunas, hot tubs, golf course, and restaurants for a fee.

Guest favourite

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.

Guest favourite

Condo in Brewster

4.93 out of 5 average rating, 60 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.

Top Guest favourite

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

Guest favourite

Apartment in Brewster

5 out of 5 average rating, 23 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!

Guest favourite

Apartment in Hyannis Port

4.89 out of 5 average rating, 135 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.

Guest favourite

Condo in Brewster

4.92 out of 5 average rating, 26 reviews

Escape to the Cape

PRIVATE QUIET COMMUNITY overlooking Cape Cod Bay. 3 Spacious Bedrooms, 2 Baths, (Sleeps 6) 3 minute walk to exclusive private beach, community pool & 2 tennis courts Relax, Sun, Swim, Shop – Stroll the Beach During the Summer Season, we rent Sunday ~ Sunday to avoid the traffic on the Mid Cape Highway. Take a well deserved break in this cozy, well appointed 3 bedroom bay-side vacation rental. We hope to host you soon! ~Betsy & Jonathan

Guest favourite

Home in Plymouth

4.9 out of 5 average rating, 129 reviews

Seaview Summit | Ocean Views, Indoor Pool, Beach

Perched above the coastline with panoramic Atlantic views, Seaview Summit House is Plymouth's premier oceanfront retreat. Designed for discerning travelers seeking serenity, space, and sophistication. With a heated indoor pool, expansive outdoor living areas, and direct beach access just moments away, this stunning property delivers a five-star experience in every season. Book your stay today. You'll be glad you did.