Vacation rentals with a pool in Tisbury

Guest suite in Centerville

4.99 out of 5 average rating, 101 reviews

“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.

FamilyLocationIndoor spaces

5.0 out of 5 average rating, 19 reviews

A cozy living area features a light-colored sofa along with two blue armchairs, creating a comfortable seating arrangement. Natural light fills the space through large windows, while an entertainment unit is present with a flat-screen TV. Decorative pillows and a round coffee table enhance the inviting atmosphere.

Home in Oak Bluffs

Chic Oak Bluffs Home with Hot Tub, Walk to Town

A chic coastal escape where upscale comfort meets effortless Vineyard charm. Nestled in the heart of Oak Bluffs and just a 15-minute stroll to Circuit Avenue and the beach, this 3-bedroom, 2-bath home is designed with elegance and ease in mind. Enjoy a serene coastal palette, brand new furnishings, a spacious deck for outdoor dining, and generous yards perfect for barbecues, games, and slow summer mornings. This cozy retreat is ideal for families or couples. It's a modern twist on island living!

ValueLocationLayout

4.96 out of 5 average rating, 141 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 6/20-9/15/26. The reviews tell all!

LocationValueCheck-in

4.97 out of 5 average rating, 39 reviews

A sandy beach extends toward calm waters bordered by a tree-lined shore, creating a serene natural setting. The gentle curve of the waterway leads to a distant point, where lush greenery enhances the picturesque landscape. The bright blue sky adds to the tranquil atmosphere.

Home in East Falmouth

Renovated ranch with pool access

Renovated home in E. Falmouth offers endless relaxation and recreation: swim, bike, fish, kayak, walk, lounge. Short walk to Assoc beach or to the Seashores Clubhouse pool (seasonal). Bring your kayak: explore Washburn Island & Waquoit Bay. Sleeps 6 with 1-floor living, AC, laundry, large back deck, and outdoor shower. Nearby, you'll find dining/shopping areas, wineries/breweries, & more. A short drive to Woods Hole offers fast boats to Martha's Vineyard. Book now and enjoy Sandy Feet Retreat.

FamilyLocationParking

4.99 out of 5 average rating, 100 reviews

Home in Sandwich

"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!

LocationFamilyWalkability

4.96 out of 5 average rating, 28 reviews

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.

Home in Cotuit

ShoestringBayHouse, waterfront & pool in Cotuit

Rent four nights: get the 5th night for $49 Prime Summer 2027: rates in the area of $10,000-13,775; please inquire Welcome to ShoestringBayHouse in Cotuit, waterfront on Popponesset Bay. It's all about the views. Our home overlooks the pool, beach and bay. We include: 2-Bikes, 2-Kayaks, and a Barnstable beach pass with beach chairs. Pet friendly and spacious with 4 BR/ 4.5 baths is priced for six adult guests plus children. Pool: May 15th through late October

FamilyLocationOutdoor spaces

4.89 out of 5 average rating, 108 reviews

The exterior of the cottage features a well-maintained lawn with lush green trees in the background. A wooden deck extends from the house, along with patio chairs overlooking a tranquil pond surrounded by vibrant flowers and plants.

Cottage in Centerville

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.

LocationValueSleep quality

Apartment in Hyannis Port

A private deck is showcased with outdoor furniture, including a round table and chairs. A colorful striped umbrella provides shade, while surrounding greenery and flowers add a natural touch. The deck is well-lit by sunlight, creating a warm and inviting space.

4.91 out of 5 average rating, 158 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.

LocationFamilyBiking

4.97 out of 5 average rating, 179 reviews

Condo in New Seabury

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.

FamilyLocationDecor

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.

4.94 out of 5 average rating, 50 reviews

Coastal Charm New Seabury: 5BRs with Private Pool

Welcome to our sunny 5-bedroom New Seabury home! Perfect for families, we offer an open layout, full kitchen, and coffee bar. Relax on the deck, enjoy our fire pit, or swim in our heated saltwater pool (open mid-May to Oct). We’re just 5 mins from South Cape Beach and close to Mashpee Commons and the Popponesset Marketplace. Come make memories in our little slice of Cape Cod paradise! We’d love to host your next getaway!

ValueFamilyBackyard

4.9 out of 5 average rating, 174 reviews

A heated indoor pool is framed by sleek gray walls and illuminated with recessed lighting. Large sliding glass doors offer a view of the outdoor patio. Colorful pool floats and equipment are neatly arranged nearby, providing options for leisure activities.

Home in Plymouth

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.

FamilyValueGetting around

5.0 out of 5 average rating, 23 reviews

An inviting in-ground pool is situated within a meticulously maintained grassy area, surrounded by trees. The pool area features slate-like patio stones and is complemented by six lounge chairs organized neatly under a shaded umbrella.

Home in Edgartown

Modern & Spacious Edgartown Home with Pool

Enjoy your vacation in this wonderfully charming three bedroom home with an in-ground heated pool. Head to the beach or stay at home and go for a swim in your own backyard. There is plenty of dining room & deck space to entertain. The bike path and bus shuttle are at the end of the road (a two minute walk away). Downtown Edgartown is less than two miles away for you to enjoy shopping and multiple dining choices.

ValueLocationWifi

Popular amenities for Tisbury rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.91 out of 5 average rating, 101 reviews

Home in Wareham

Edgewater Retreat | Oceanfront Home | Heated Pool

ValueFamilyPool

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.

4.81 out of 5 average rating, 43 reviews

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

LocationFamilyGetting around

4.73 out of 5 average rating, 226 reviews

An indoor pool area features large windows and skylights that allow ample natural light. A tropical plant in a pot is positioned in the foreground. The pool is surrounded by a spacious deck with seating options, providing a relaxed environment for enjoyment.

Home in New Bedford

Poseidon's Palace - 2.0

LocationValueGetting around

4.8 out of 5 average rating, 5 reviews

Home in Falmouth

Pool Escape in East Falmouth

LocationFamilyPets

5.0 out of 5 average rating, 25 reviews

Home in Sandwich

Family Cape Cod Oasis-Pool-Hot Tub-Game&Kids Room

LocationFamilyLayout

5.0 out of 5 average rating, 28 reviews

The exterior of the ranch-style home features a spacious deck with seating and a hammock, surrounded by landscaping. Kayaks are available below the deck, and large windows provide ample natural light. The property is set within a green, tree-lined area, enhancing the outdoor appeal.

Home in East Falmouth

Waterfront Home w/Dock, Deck, Central A/C & Kayaks

LocationFamilyParking

4.97 out of 5 average rating, 30 reviews

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

Modern Cape Cod home steps to beach; pool access!

LocationFamilyGetting around

A refreshing swimming pool is surrounded by a concrete deck, featuring several lounge chairs positioned along one side. Umbrellas provide shade near the pool's edge, and a fenced yard is adorned with greenery, creating a serene outdoor setting.

4.96 out of 5 average rating, 28 reviews

Beach Pass Included! Brand New Spa! Central AC!

LocationValueLayout

Condo rentals with a pool

4.92 out of 5 average rating, 49 reviews

A clear blue swimming pool is surrounded by lounge chairs positioned for relaxation. Lush greenery provides a natural backdrop, while a shaded area offers protection from the sun. Steps lead from the pool to a nearby structure, adding convenience for guests.

Condo in Tisbury

Private 3bdrm Condo Tashmoo Woods

FamilyValueTV

4.71 out of 5 average rating, 31 reviews

A bright living area features a navy blue sectional sofa and a wooden dining table with four chairs. Light streams in through a large window adorned with green curtains, complementing a coastal-themed wall art piece. A cozy area rug lies beneath a wooden coffee table.

Condo in Tisbury

Heart of VH, w/ac, pool & harborview

FamilyLocationBiking

4.67 out of 5 average rating, 9 reviews

An aerial view captures the resort's layout alongside the coastline. Sandy beach stretches along the water's edge, while the Atlantic Ocean meets a calm bay. Behind the resort, residential areas are interspersed with patches of greenery, illustrating the natural beauty surrounding the location.

Condo in Falmouth

InnSeason Resorts Surfside

FamilyLocationBackyard

A spacious pool area is enclosed by a white fence, surrounded by lush greenery. Lounge chairs are positioned around the edge of the inviting water, with trees and houses framing the scene in the background. The sky transitions to soft hues during sunset.

Condo in Tisbury

4.96 out of 5 average rating, 26 reviews

Relax....You're on Island Time......

FamilyLocationIndoor spaces

A spacious living area features a large dark leather sectional sofa with decorative pillows. The room is illuminated with natural light and displays coastal-themed artwork on the walls, adding a relaxed atmosphere. A sliding barn door is visible, contributing to the modern design.

Condo in Falmouth

4.84 out of 5 average rating, 19 reviews

Falmouth MA, Cape Cod Getaway

LocationFamilyNearby

A community pool is surrounded by a tan deck and green lounge chairs. The pool features clear blue water and a ladder for entry. Lush greenery provides a natural backdrop, with a few buildings visible in the distance, emphasizing a peaceful environment.

Condo in New Seabury

4.89 out of 5 average rating, 19 reviews

Bright, Coastal Mashpee Condo Near the Commons

FamilyLocationBeach

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

4.5 out of 5 average rating, 6 reviews

Condo w/ Private Balcony + Pool Access in Mashpee

LocationFamilyKitchen

A relaxing outdoor pool area features lounge chairs arranged along the pool's edge. The surrounding building, showcasing spacious balconies, houses multiple units. Guests enjoy sunbathing and walking nearby, with clear skies overhead enhancing the scene.

Condo in Falmouth

5.0 out of 5 average rating, 4 reviews

Two bedroom condo .on the water Falmouth, ma

FamilyLocationBeach

Other vacation rentals with a pool

5.0 out of 5 average rating, 71 reviews

The exterior of a spacious cottage is displayed, framed by vibrant green lawns and seasonal flowers. A stone pathway leads up to the entrance, with pumpkins placed decoratively in the garden area. The clear blue sky enhances the overall inviting presence of the home.

Guesthouse in Woods Hole

Falmouth/Woods Hole Charming Cottage By the Sea

LocationComfortCondition

4.89 out of 5 average rating, 98 reviews

A lagoon-style pool surrounded by a concrete deck provides lounge chairs and shaded areas under umbrellas. A gazebo is visible in the background, complementing the lush greenery that borders the property.

Villa in Wareham

Perfect Farmhouse for groups-golf/trails/beach

FamilyLocationSleep quality

4.95 out of 5 average rating, 21 reviews

Cape Gem in New Seabury with private heated pool

FamilyLocationCondition

A serene backyard features a heated pool surrounded by paved stone decking. Multiple lounge chairs are positioned for comfort, offering views of the lush greenery. The two-story home is visible in the background, with a deck equipped for outdoor relaxation.

5.0 out of 5 average rating, 20 reviews

New Seabury Oasis with Pool!

FamilyLocationAmenities

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.

5.0 out of 5 average rating, 8 reviews

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

LocationFamilyIndoor spaces

A spacious outdoor area features a plunge pool surrounded by green grass and a stone patio. Lounge chairs are arranged nearby under a white umbrella, offering shade. The yard is bordered by trees and flowering plants, providing a serene setting for relaxation.

4.8 out of 5 average rating, 35 reviews

Swing Set, Plunge pool, and large yard await!

FamilyLocationCondition

An outdoor oasis showcases a large in-ground pool with sparkling blue water, surrounded by a wooden deck and lounge chairs. A luxurious hot tub sits nearby, with cozy lighting strung overhead, offering a serene atmosphere for relaxation and enjoyment.

5.0 out of 5 average rating, 37 reviews

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

FamilyLocationHot tub