Holiday rentals with a pool in Brewster

4.71 out of 5 average rating, 28 reviews

The exterior of the cottage-style condo displays a welcoming entrance under a clear blue sky. Lush green shrubs and flowering plants add a vibrant touch, while a grill is positioned on the porch, inviting outdoor gatherings.

Condo in Harwich Port

Cape Cod Condo,Walk to Beach, near Nantucket Ferry

Enjoy your next beach vacation at this charming cottagecore-style condo located in the quintessential seaside town of Harwich Port, just a short walk to nearby Wyndemere Bluffs beach.This delightful beach cottage includes 1 bedroom, 1 bathroom, with an additional queen pull out to accommodate 2-4 guests. Grill out on the porch, take a stroll down Main St for ice cream or lobster rolls, or take a dip in the private community pool (steps from your front door)!Nantucket ferry 1 mile down the road!

The living room features two comfortable sofas adorned with colorful cushions, situated around a wooden coffee table on a vibrant area rug. Natural light fills the space, highlighting the dining area and fully equipped kitchen visible in the background.

4.85 out of 5 average rating, 55 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!

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.

4.96 out of 5 average rating, 90 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.

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.

5 out of 5 average rating, 100 reviews

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

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.

5 out of 5 average rating, 87 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.

4.95 out of 5 average rating, 128 reviews

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

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 6/20-9/15/24. The reviews tell all!

4.98 out of 5 average rating, 105 reviews

A cozy living area is furnished with a comfortable sofa adorned with decorative pillows. A dining table with seating for four is visible, alongside a well-equipped kitchen in the background. Natural light enters through the windows, highlighting the warm wood floors.

Apartment in Wellfleet

Rock on Wellfleet!

A wonderful Wellfleet location! This second floor rental has a spacious bedroom with a queen bed, bathroom with a tub and living area with a well stocked kitchen. You would have the whole upstairs to yourself with a private door to come and go. You are also invited to use our pool at anytime! We're located very close to the Cape Cod Rail Trail for miles of bike riding, PB Boulangerie Bistro, Marconi Beach, the iconic Wellfleet drive-in and so much more. Bedding, towels and essentials provided.

5 out of 5 average rating, 32 reviews

An aerial view showcases a tranquil swimming pool surrounded by a spacious lawn. Adjacent seating areas, including sun loungers and a fire pit with chairs, are positioned within the private fenced yard. Lush greenery and garden beds enhance the outdoor space.

Home in Harwich Center

Harwich Haven: Pool & Fire Pit

Welcome to The Harwich Haven! This 4-bed, 3.5-bath retreat in Harwich, MA offers a spacious family room, modern kitchen, swimming pool, fire pit, two decks with outdoor dining, an outdoor grill, private fenced in yard, two newly renovated ensuite bathrooms with spa amenities and more. With easy access to beaches, restaurants, and shops, it's your perfect vacation getaway! Saturday to Saturday weekly rentals only July & August. 4 night Thursday to Sunday minimum in June.

4.85 out of 5 average rating, 61 reviews

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

Welcome to Mid Cape Cod. Location, Location, Location. Wake up in the morning and have coffee on your private patio. The view overlooks the well manicured back yard bordered by tress and bunnies running around. After coffee, walk down main street for breakfast and more coffee at 3 Fins. Now that you are hyped, walk across the street and rent a Kayak or SUP for the day. Paddle out the Bass river down to the Nantucket sound. Have lunch next door at Sundancers.

4.97 out of 5 average rating, 60 reviews

A pool area features a rectangular swimming pool surrounded by a stone patio. Loungers and two shaded areas offer seating options. The home in the background is two stories with white siding, and leafy trees provide a pleasant backdrop.

Home in Chatham

Luxury Beach Barn with Pool, Hot Tub & Sauna

Experience the ultimate getaway at this stunning 7-bedroom retreat, just a mile from Cape Cod’s pristine beaches. Enjoy a top-rated gourmet kitchen, a charming renovated barn, and a Catina Pool Bar perfect for poolside relaxation. With a sparkling pool and a soothing sauna, this home offers the perfect blend of elegance and comfort. This property is ideal for family vacations, group getaways, and special celebrations. Book now No events allowed.

4.97 out of 5 average rating, 162 reviews

A welcoming living area features a comfortable sectional sofa and two wooden armchairs arranged around a circular coffee table. Natural light fills the space, highlighting a large area rug on the hardwood floor. A well-equipped kitchen is visible in the background.

Condo in New Seabury

Sleep 6 @ New Seabury w/ Pool Access, All Seasons!

Welcome to Your Coastal Getaway at The Mews, New Seabury – Mashpee, MA Tucked inside the beautiful New Seabury Country Club, our cozy Cape-style condo offers the perfect balance of relaxation and adventure on Cape Cod. Enjoy access to a private condo association pool just a 3-minute walk away, and a beach that is 5 min drive or 10 min bike ride or 30 min walk (walk cuts through golf course-ask host for directions).

Apartment in Hyannis Port

An inviting living space is highlighted with a grey sofa, modern dining table with four chairs, and bright windows allowing natural light. The kitchen has sleek cabinets and appliances. Below, the scenic Keyes Memorial Beach is shown with soft sand and a sunset. A community pool featuring turquoise water and lounge chairs is also visible.

4.87 out of 5 average rating, 102 reviews

Cute Cottage Near Beach & Main Street 3BR/3BA (15)

Stay at a charming 3-Bedroom cottage in a beautiful setting within walking distance to Cape Cod's warm sandy beaches and Main Street Hyannis. Captain Gosnold Village is ideally located within a short walk from three of the Cape's best beaches and nestled between picturesque Hyannis Port and the vibrant atmosphere of Hyannis Harbor with its island ferries, sightseeing and fishing charters.

Popular amenities for Brewster rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 43 reviews

An aerial view captures the estate's expansive layout, featuring two charming buildings, a central saltwater pool, and a clay tennis court. Surrounded by greenery, the property showcases landscaped areas and pathways, creating an inviting outdoor space suitable for various activities.

Home in East Sandwich

XL Estate: 2 Homes-Pool-Tennis-Game Barn - 20 ppl

4.8 out of 5 average rating, 30 reviews

An inviting outdoor space is depicted, featuring a spacious in-ground pool surrounded by lounge chairs. String lights are strung across the pool area, illuminating the backyard. A pool house and umbrellas provide additional amenities, while the home's facade is visible in the background.

Home in Barnstable

Stunning Cape Home - Inground Pool, 5 Min To Beach

4.91 out of 5 average rating, 33 reviews

The backyard features an inground pool illuminated at night, surrounded by wooden decking. Nearby, a shed with white shutters enhances the outdoor space, while lush greenery provides a serene backdrop.

Home in Orleans

5-bedroom Cape with a pool and yard games.

4.88 out of 5 average rating, 40 reviews

Home in Barnstable

Beachside Retreat pool&spa bball court

5 out of 5 average rating, 7 reviews

An inviting outdoor area features a heated in-ground pool surrounded by a wide patio of pavers. Sun loungers are positioned near the water, and a dining set is shaded under an umbrella. Lush greenery is visible in the background, providing a sense of privacy.

Home in Popponesset

49 Clover Lane, 3 beds, 3.5 baths, pool & firepit

4.94 out of 5 average rating, 18 reviews

A bright bedroom features a spacious bed with striped bedding and decorative pillows. A cozy throw blanket is placed at the foot of the bed. Natural light filters through the two windows, and a floor lamp adds additional lighting. A framed art piece is mounted on the wall.

Home in East Sandwich

Coastal Retreat in Sandwich -Pool Access, Dogs OK!

4.92 out of 5 average rating, 49 reviews

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 15

4.94 out of 5 average rating, 79 reviews

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 East Sandwich

Large Home Heated Swimming Pool Private Beach

Condo rentals with a pool

A spacious sleeping area features a large bed with neutral bedding and colorful accent pillows. A TV is mounted on the wall. Natural light filters through a sliding glass door, which opens to an outdoor area with a small table and chairs.

4.82 out of 5 average rating, 74 reviews

Cozy Studio Just Steps Away From the Beach!

The spacious living area features a queen-sized bed and a comfortable sofa. A dining table with two chairs sits near the window, allowing natural light to brighten the room. Simple decor includes star-shaped wall accents, enhancing the relaxed coastal ambiance.

4.84 out of 5 average rating, 87 reviews

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

A living area is highlighted by a large window offering a view of the ocean. Soft blue curtains frame the window, while a modern TV is mounted on the wall. A gray sectional sofa is arranged near a glass coffee table, with a dining table set for four nearby.

5 out of 5 average rating, 3 reviews

Ocean Breeze

An outdoor saltwater pool is framed by comfortable lounge chairs under clear blue skies. Lush greenery surrounds the pool area, providing a serene atmosphere for relaxation and enjoyment. A set of steps leads into the inviting water.

Condo in Mashpee

1BR Condo w/ Balcony in Mashpee, MA

4.82 out of 5 average rating, 17 reviews

A serene waterfront view features a wooden dock extending into calm waters, reflecting a colorful sunset with shades of orange and blue. Silhouettes of boats and poles can be seen against the horizon, enhancing the tranquil atmosphere.

Condo in Hyannis Port

Beachfront Complex in Hyannis

The view captures a beachside setting with blue waters and gentle waves lapping at the shore. Multiple buildings with light-colored façades line the beach, showcasing balconies and decks. The sandy beach features scattered rocks, leading to open dunes under a clear sky.

5 out of 5 average rating, 4 reviews

Oceanfront beach house - Entire 1st floor

4.97 out of 5 average rating, 67 reviews

A bright and airy studio features a queen bed with a soft blanket, paired with a small dining table and chairs. The kitchenette is equipped with modern appliances, while a flat-screen TV hangs above. A large window opens to a private balcony with outdoor seating.

Condo in West Dennis

Oct + Nov Discount | Central | Private Balcony

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.

4.91 out of 5 average rating, 115 reviews

The Sea Salt Studio - Steps to the Beach!

Other holiday rentals with a pool

5 out of 5 average rating, 7 reviews

A spacious deck features a wooden dining table with matching chairs, overlooking a private heated pool and serene water views. Lush greenery surrounds the area, while a private dock is visible along the shoreline.

Home in New Seabury

Waterfront Home w/ Dock, Heated Pool, Kayaks & A/C

5 out of 5 average rating, 15 reviews

A charming single-story home is presented with a neatly manicured lawn, adorned with blooming blue hydrangeas. A flag is displayed on the front porch, and large windows provide a view of the inviting interior. The clear blue sky complements the home's fresh appearance.

Home in Hyannis Port

Renovated Cape Oasis W/ New Pool and Game Room!

5 out of 5 average rating, 14 reviews

Home in South Yarmouth

Fenced Pool, Fire pit, Outside dining, Coffee bar

4.94 out of 5 average rating, 16 reviews

An outdoor area features a spacious table with four chairs under a large yellow umbrella, providing shade. Nearby, a private hot tub is tucked away among trees, while a small white side table and a blue adirondack chair complete the relaxing ambiance.

Home in Dennis Port

Sauna, Hot Tub, Walk to Beach -Seaglass Cottage

4.88 out of 5 average rating, 24 reviews

The exterior of the home is presented with natural wood siding, complemented by green shutters. Solar panels are mounted on the roof. A welcoming front porch leads to the main entrance, while a garage is visible to the left amidst well-maintained landscaping.

Home in Harwich Center

4 BD slice of Harwich Heaven

The exterior of a blue townhome is shown, featuring a red door and white trim. Lush green landscaping surrounds the entrance, with a well-kept lawn and mature trees in the background. A paved pathway leads up to the front door.

Townhouse in Brewster

4.86 out of 5 average rating, 22 reviews

Coastal Oasis: Brewster-Cape Cod

5 out of 5 average rating, 26 reviews

An in-ground pool is surrounded by a spacious patio, featuring several blue lounge chairs. Lush greenery frames the area, with a clear blue sky overhead. The pool’s water reflects the sunlight, creating a refreshing ambiance for relaxation and entertainment.

Home in Hyannis Port

Hyannis Port Coastal Escape – Pool & Walk to Beach