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Vacation rentals with a pool in Osterville

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Osterville

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Top guest favorite

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

5 out of 5 average rating, 23 reviews

Hyannis Port Coastal Escape – Pool & Walk to Beach

Welcome to "The Sand Box” in Hyannis Port, our Cape Cod Rental. We can’t wait to answer all your questions about our property! Our home is 4 bedroom, 2 full bath that was fully renovated in October of 2021. It’s walking distance to two beaches and central to many more across Barnstable. Lush outdoor entertainment area with an in-ground pool and patio with an outdoor gas grill. 5 minute drive from downtown Hyannis. It’s a fantastic getaway for 4 couples or for a whole family. Cert# C0457270200

A spacious backyard is highlighted by a large solar-heated pool, surrounded by a stone patio with lounge chairs and umbrellas. The well-maintained house is framed by lush trees and colorful foliage, creating a peaceful outdoor retreat.

Home in Barnstable

5 out of 5 average rating, 6 reviews

CapeSearenity-Large Pool-Beach Passes-Family Fun!

Visit Cape SeaRenity–a stunning home w/solar heated pool and outdoor lounge, perfect for a memorable family vacation and a fabulous Cape Cod experience. Escape to Cape SeaRenity—a beautifully updated home near Barnstable Village with a pool, outdoor lounge, & stylish interiors. Minutes from beaches, shops, dining, & whale-watching. Enjoy a modern kitchen, game-filled garage, bikes & kayaks. With thoughtful design & ProHost® support, it’s the perfect base for exploring Cape Cod with your family.

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.

4.95 out of 5 average rating, 127 reviews

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!

Top guest favorite

A cozy seating area is presented with woven furniture beneath soft lighting. The pool glistens quietly in the background, surrounded by natural scenery. The space allows for relaxed outdoor gatherings, with easy access to the water views beyond.

Apartment in Barnstable

4.94 out of 5 average rating, 53 reviews

Studio Apartment

Private Studio apartment on lower level of Main House with deck overlooking Pond. Queen bed, single sleeper sofa and small sleeping loft. Very comfortable for 2 people but could sleep up to 4. Kitchenette with dinnerware and cookware. Coffee maker, full size fridge, microwave, toaster oven, outside gas grill. Private bath with shower. TV, WiFi, A/C. Pond access, SUP, kayaks available. Pool and hot tub at Main House. Sunrise views. Golf courses, shopping, restaurants, and beaches nearby.

Condo in Brewster

4.97 out of 5 average rating, 189 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!

An indoor heated saltwater pool is surrounded by large windows that invite natural light. The space is accented by sleek white walls and high ceilings with skylights. A hot tub is visible near the pool, contributing to a relaxing atmosphere.

Villa in New Seabury

4.98 out of 5 average rating, 52 reviews

Heated Indoor Pool & Spa - Golf Course View

CHERRY BLOSSOM RETREAT Cold days, raining days and power outage won't hinder your stay at this luxurious home, boasting an indoor heated salt water pool and hot tub fully equipped with a backup generator, overlooking the renowned 3-Hole Championship Golf Course. Our ultimate luxury home features an array of indoor entertainment options including arcades, air hockey, foosball PS5, Switch, etc. comfortably accommodating 6 to 8 guests, and merely a short drive to all all New Seabury's amenities.

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.

Condo in Dennis Port

4.91 out of 5 average rating, 111 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.

Top guest favorite

Home in Sandwich

4.99 out of 5 average rating, 89 reviews

"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!

The spacious outdoor area features a heated saltwater pool surrounded by paver stones. Lounge chairs are positioned around the pool, accompanied by blue umbrellas. A nearby cabana is visible, along with vibrant landscaping, providing a relaxing atmosphere for guests.

Home in Popponesset

5 out of 5 average rating, 16 reviews

18 Menemsha Rd., Popponesset, Pool, 3-Beds, 4 bath

This home was custom built in 2022, and is designed to provide comfort, luxury and loads of charm for the discerning vacationer. New construction with a nod to the Nantucket Sea Captain's houses of yesteryear. Professionally decorated and landscaped, offering every amenity you could possibly desire; from an in-ground, heated, saltwater pool (with electric cover), hot tub, outdoor shower, fire-pit, and even a cabana with a sink, refrigerator, and smart TV. Just a 3 min walk to private beach.

Top guest favorite

The pool area features two lounge chairs positioned beside a sparkling blue pool. Surrounding lush greenery and flowering bushes create a secluded ambiance, with a hint of sun shining down on the concrete patio, offering a serene outdoor space for relaxation.

Guest suite in Centerville

4.99 out of 5 average rating, 89 reviews

Cape Cod Hideaway

Enjoy a bit of Cape Cod in a neighborhood of lush green trees , flower gardens, and a walking trail. Less than 1 mile from Centerville's shops and restaurants. Only 2 miles from Craigville Beach and its beachside walk up shanty’s for fresh seafood / burgers. Main street Hyannis is the "Hub" of the Cape and a quick 10-minute drive. Explore the many beaches and local fare by day and the lively clubs at night. Ocean docks, marinas, and ferries to the islands are a 10–15-minute drive.

A crystal-clear pool is surrounded by a fenced patio, featuring two white adirondack chairs and a red lounge chair nearby. Lush trees and green grass create a serene backdrop, while a spacious yard extends into the distance, enhancing the outdoor leisure space.

Cottage in Centerville

4.93 out of 5 average rating, 98 reviews

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.

A spacious in-ground pool is surrounded by a sunbathing area featuring a lounge chair and umbrella. Lush greenery and flowering bushes frame the backyard, while a pool house is visible in the background, equipped with comfortable seating. The pool area invites relaxation and enjoyment.

Home in Barnstable

4.83 out of 5 average rating, 29 reviews

Stunning Cape Home - Inground Pool, 5 Min To Beach

Stunning in-ground pool. Just 5 minutes from Craigville, Dowses and Covell's Beach! Perfect for mid-size groups or families, this home sleeps 8 and boasts a dreamy, private, fenced-in backyard w/ a, pool house w/ TV & bar, outdoor shower, and cozy patios. Complete w/ all your beach essentials. Conveniently located, we're 13 minutes from Mashpee Commons and 10 minutes from local grocery stores, local bakeries& restaurants. Central to all the Cape has to offer!

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Popular amenities for Osterville rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

The charming exterior of the newly renovated home is highlighted by a sloping roof and a welcoming front door. Framing the entrance are neatly trimmed bushes and a small pathway leading to the door. A garage is located on the side, complemented by grassy green surroundings.

Home in Falmouth

5 out of 5 average rating, 23 reviews

Home in Falmouth ~ 5 min drive to beach

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

4.93 out of 5 average rating, 15 reviews

Sauna, Hot Tub, Walk to Beach -Seaglass Cottage

A light-filled living area features comfortable seating with blue and white accents. A natural wood coffee table sits in the center, surrounded by a cozy area rug. A separate dining space is visible through an open archway, showcasing a charming dining table and decorative elements.

Home in Plymouth

4.73 out of 5 average rating, 67 reviews

Plymouth Family Retreat with Pool

Top guest favorite

A spacious, inviting pool is surrounded by a stone patio and lush greenery. Several lounge chairs are positioned around the pool, offering relaxation spots. The clear blue water reflects the sunlight, while a gentle slope leads to a grassy area beyond.

4.93 out of 5 average rating, 58 reviews

Cape Cod Lakefront Home

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 Sandwich

4.92 out of 5 average rating, 13 reviews

Coastal Retreat in Sandwich -Pool Access, Dogs OK!

The home's exterior features a spacious deck with a spacious area for outdoor seating. A private, unheated inground pool is visible in the foreground, surrounded by a paved patio. Lush greenery provides privacy, enhancing the tranquil atmosphere.

Home in Falmouth

4.87 out of 5 average rating, 31 reviews

Sippewissett Forest Magic by the Sea

An inground pool is surrounded by a spacious patio with lounge chairs and a gazebo, offering a shaded area. Lush green grass and trees enhance the outdoor setting, creating a relaxing environment for recreation and leisure.

Home in Plymouth

4.82 out of 5 average rating, 33 reviews

The Plymouth Pool House

The image shows a spacious pool area surrounded by sun loungers. The inviting inground pool is complemented by a paved patio, featuring a vibrant array of floats. Lush greenery enriches the setting, while adjacent outbuildings provide additional outdoor space.

Home in Falmouth

4.96 out of 5 average rating, 28 reviews

Secluded Cape Cod home in Falmouth with pool

Condo rentals with a pool

A clean outdoor pool is framed by a spacious concrete deck with lounge chairs positioned nearby. Lush greenery and landscaped areas are visible around the pool, contributing to a serene environment. The sky above is clear, enhancing the bright atmosphere of the setting.

Condo in West Dennis

4.93 out of 5 average rating, 42 reviews

1BR 2nd Floor Condo with pool

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.

Condo in Brewster

4.84 out of 5 average rating, 51 reviews

Ocean Edge: 2 bed/2 bath - Pools & Resort Access

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.

Condo in Brewster

4.95 out of 5 average rating, 82 reviews

Ocean Edge 2 Bed 2 Bath, Golf & Free Resort Access

A clear blue pool is surrounded by lounge chairs, offering a refreshing spot for relaxation. The two-story building in the background features balconies with umbrellas and well-maintained landscaping, creating a serene atmosphere for guests.

Condo in West Dennis

4.84 out of 5 average rating, 58 reviews

Hidden Hideaway

The entrance of the condominium is shown, featuring a wooden exterior with shingles. A pathway leads to the door, surrounded by neatly trimmed shrubs and grass. Bright sunlight highlights the clear sky and the inviting pathway.

Condo in Falmouth

4.7 out of 5 average rating, 27 reviews

Condo in Falmouth MA

A crystal-clear pool is framed by a deck lined with blue lounge chairs. The setting includes landscaped greenery and trees, with two-story buildings in the background providing serene surroundings. The clear blue sky enhances the tranquil atmosphere of this communal outdoor space.

Condo in West Dennis

4.86 out of 5 average rating, 56 reviews

Mid Cape Cod, 3 Season Haven by Bass River

Condo in Brewster

5 out of 5 average rating, 84 reviews

Ocean Edge Resort/Pool access/2bedroom-2bath Condo

A clear blue swimming pool is visible in the foreground, surrounded by a spacious deck with lounge chairs. The two-story building showcases multiple windows and a covered porch area, providing a view of the pool. A white fence encircles the pool area.

Condo in Falmouth

5 out of 5 average rating, 8 reviews

Spacious 2BR by the Sea in Falmouth

Other vacation rentals with a pool

The exterior of the house is presented, featuring a light-colored facade with a black roof and six front-facing windows. A porch is accessible with seating arranged nearby. A well-maintained lawn with flower beds is visible, complemented by a gravel driveway and American flag displayed.

Home in East Falmouth

5 out of 5 average rating, 23 reviews

Modern Cape Cod home steps to beach; pool access!

Top guest favorite

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

5 out of 5 average rating, 15 reviews

Renovated Cape Oasis W/ New Pool and Game Room!

A private pool area features a rectangular swimming pool surrounded by a concrete deck. Several blue lounge chairs are positioned along the perimeter. Lush greenery and trees provide secluded shade, while a gravel pathway leads to the pool area, enhancing the outdoor experience.

Apartment in West Dennis

4.95 out of 5 average rating, 22 reviews

Town House for Cape Cod fun, by Bass River.

A private swimming pool is surrounded by a spacious patio, featuring comfortable lounge chairs for relaxation. The home, with a light-colored facade, is partially visible in the background, showcasing large windows and a deck that overlooks the picturesque outdoor space.

Home in Barnstable

4.71 out of 5 average rating, 21 reviews

New Pool, beach, kayak, Marina in Barnstable.

An aerial view reveals a spacious bay front home surrounded by lush greenery. A large pool is visible in the backyard, with steps leading down to a beach area featuring kayaks. The residence is set in a tranquil, wooded environment.

4.95 out of 5 average rating, 20 reviews

ShoestringBayHouse, waterfront & pool in Cotuit

An aerial view captures the spacious property featuring a well-maintained in-ground pool surrounded by a fenced area. Lush gardens and trees in various autumn colors frame the grounds, with expansive fields visible in the background, offering a serene outdoor setting.

Home in Sandwich

5 out of 5 average rating, 6 reviews

Saltfish Bay - Heated Pool and Beach Access

A seasonal swimming pool is covered and secured, bordered by a concrete patio. Several outdoor seating options are visible, including a round table with chairs. The surrounding area features a mix of grass and fencing, with trees softly framing the space.

Cabin in Falmouth

4.67 out of 5 average rating, 607 reviews

Waterside Guest House

An aerial view of a spacious property featuring a uniquely shaped heated saltwater pool surrounded by a stone patio. A large deck is positioned next to the pool, with several lounge chairs arranged nearby and greenery framing the area.

Home in New Seabury

4.93 out of 5 average rating, 30 reviews

Home w/ golf view, salted heat pool, mins to beach

Quick stats about vacation rentals with a pool in Osterville

Total rentals
20 properties
Nightly prices starting at
R9,652 ZAR before taxes and fees
Total number of reviews
180 reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace

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