Vacation rentals with a pool in Tisbury

Guest suite in Centerville

“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.

4.99 out of 5 average rating, 107 reviews

5.0 out of 5 average rating, 23 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!

4.96 out of 5 average rating, 147 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!

5.0 out of 5 average rating, 71 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 Sandwich

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

Our Cape Cod Estate is truly one of a kind. This 2+ acre retreat boasts an extraordinary design built in the 1800s and updated with modern luxuries. Enjoy room for up to 20 guests with two homes, a separate bar and game barn and tons of amenities! Centrally located within 5 minutes of three public beaches, shops, dining & golf! The perfect getaway for family reunions, group vacations, wedding parties, corporate retreats, and more! SUMMER MONTHS: - Weekly bookings only - Saturday to Saturday

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.

4.98 out of 5 average rating, 43 reviews

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.

4.73 out of 5 average rating, 33 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

Enjoy your stay on Martha’s Vineyard in Causeway Harborview condos with this 2 bedroom/1 bathroom unit. - Views of the harbor from the unit - Pool & Laundry on-site - Parking on-site - Walk to ferry, restaurants, shops and beach - Bike to Oak Bluffs - All linens provided - Fully equipped kitchen with coffee and tea provided - Beach gear provided My goal is to provide guests with a 5-star experience, if there is anything that can improve your experience that isn’t listed, just ask!

4.92 out of 5 average rating, 50 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

This 3 bedroom (3 king) 2 1/2 baths newly renovated condo is in a private setting with screened in porch. New kitchen, gas grill on deck, outdoor shower. -Access to the Tashmoo Woods Association pool, tennis courts and play ground. -Close to West Chop beaches. -Two miles from downtown Vineyard Haven. On bus route, but best to have a car. -The primary bedroom (king bed) is downstairs and the 2 upstairs bedrooms share a bath (shower only). Minimum rental 5 days, 1 week in summer.

4.94 out of 5 average rating, 111 reviews

A cozy studio space features sloped ceilings and warm wooden flooring. A spacious bed is dressed in white linens, with accent pillows adding a touch of color. A small kitchenette is visible beside a comfortable chair and a blue rug, offering a relaxed atmosphere.

Guest suite in Dartmouth

The Loft @ Beechwood. Private, comfy, coastal!

The Loft is a detached and private studio apartment with a private entrance, beautifully decorated with a coastal decor befitting nearby Padanaram Harbor & Village. The skylights and a 'really, really comfortable bed' will help you relax and enjoy all the area has to offer. Ideal for two guests, but able to accommodate a third, or two children, The Loft is a great home base to explore the local area or the Islands of Cuttyhunk, Martha's Vineyard & Nantucket.

4.97 out of 5 average rating, 185 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.

4.94 out of 5 average rating, 53 reviews

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

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!

4.9 out of 5 average rating, 181 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.

5.0 out of 5 average rating, 26 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.

Popular amenities for Tisbury rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.74 out of 5 average rating, 233 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

4.97 out of 5 average rating, 32 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

4.93 out of 5 average rating, 15 reviews

Cape Cod Escape at Casa de Leo!

5.0 out of 5 average rating, 8 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

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.

4.97 out of 5 average rating, 31 reviews

Modern Cape Cod home steps to beach; pool access!

5.0 out of 5 average rating, 32 reviews

Home in Sandwich

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

The two-story home features a sleek white exterior with black accents. A set of wide steps leads to the front door, framed by large windows. A well-maintained lawn and driveway provide access, while trees gently surround the property, ensuring a sense of privacy.

5.0 out of 5 average rating, 32 reviews

Beautiful home! Clubhouse pool, tennis, basketball

4.86 out of 5 average rating, 7 reviews

Home in Falmouth

Pool Escape in East Falmouth

Condo rentals with a pool

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

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

4.97 out of 5 average rating, 29 reviews

Condo in Oak Bluffs

Island Inn - Two Bedroom Suite - 1A - Oak Bluffs,

4.75 out of 5 average rating, 4 reviews

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

Bright, Coastal Mashpee Condo Near the Commons

4.9 out of 5 average rating, 20 reviews

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

Condo in Falmouth MA

4.72 out of 5 average rating, 47 reviews

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

Falmouth MA, Cape Cod Getaway

4.84 out of 5 average rating, 19 reviews

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

Condo w/ Private Balcony + Pool Access in Mashpee

4.5 out of 5 average rating, 6 reviews

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

Two bedroom condo .on the water Falmouth, ma

5.0 out of 5 average rating, 5 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

4.78 out of 5 average rating, 18 reviews

Other vacation rentals with a pool

5.0 out of 5 average rating, 4 reviews

Apartment in Edgartown

Cozy downtown apartment

5.0 out of 5 average rating, 73 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

4.83 out of 5 average rating, 12 reviews

Private Saltwater Pool, Game Room, near Beaches!

5.0 out of 5 average rating, 12 reviews

Resort Home Pool, Hot Tub, Pickleball, Movie, Pets

4.95 out of 5 average rating, 92 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 Sandwich

Large Home Heated Swimming Pool Private Beach

4.92 out of 5 average rating, 24 reviews

Home in New Seabury

Cape Gem in New Seabury with private heated pool

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.

4.78 out of 5 average rating, 50 reviews

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

The exterior of the Cape Cod home presents a blend of shingle and clapboard siding in soft colors. Large windows are framed by well-maintained greenery and landscaping, adding to the home’s welcoming character. The setting is peaceful, surrounded by trees and lawn space.