Holiday rentals with a pool in Oak Bluffs

An outdoor pool area showcases a heated inground pool with clear water, surrounded by a wooden deck. Sun loungers are placed nearby, and patio umbrellas provide shade. Lush greenery and trees line the background, offering a serene environment. A beach ball floats in the water.

4.85 out of 5 average rating, 33 reviews

Exclusive New Seabury Home w/ Heated Pool ⛳️🏖🦞☀️🐠

~~ You Have Arrived! Welcome to "The Fore Seasons" in desirable New Seabury on Cape Cod. ⛳️🏖🌸☀️ You will be sure to fall in love with old Cape Cod in this 4,500 sqft private home located on the 10th hole fairway of the championship golf course. With its 4 bedrooms, 4 bathrooms, Heated Inground Pool, Outdoor Shower, Putting Green, Ping Pong table and Ctrl Air there is enough room for the largest families. Pool open from Mid-May until through Columbus Day! Available year round for all gathering

5 out of 5 average rating, 14 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!

The exterior of the villa is framed by lush greenery and flowering shrubs. A brick pathway leads to a welcoming entrance, featuring a single red door. The home is situated in a peaceful residential area, surrounded by mature trees and landscaping.

4.95 out of 5 average rating, 19 reviews

Cape Gem in New Seabury with private heated pool

Our Pristine, Newly Renovated, Patio home with Private heated Pool (RENOVATED 2026), located in the Mews of New Seabury, offers the privacy and peacefulness for the perfect vacation. The sandy local beaches—South Cape Beach and Popponesett—are both very short drive away (5-10 minutes)! Highlights of the seashore resort community of New Seabury: Mashpee Commons (fine dining, shops, movie cinema), golf courses, boating, walking trails, close proximity to ferries to Nantucket and Martha’s Vineyard.

4.95 out of 5 average rating, 132 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!

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 out of 5 average rating, 17 reviews

New Seabury Oasis with Pool!

Relax with the whole family at this peaceful New Seabury retreat. 5 bedrooms, 3 bathrooms with separate living rooms on each floor. Newly updated backyard and heated pool. Backs up to 10th/11th hole of the Ocean Course at New Seabury. Great for a large family or two families to share. Master bedroom has built in desk space to allow to work from home, as needed. Walk to Popponessett marketplace and all the beautiful outdoor space New Seabury has to offer. Short drive to South Cape beach.

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.

Apartment 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.

Guest house in Woods Hole

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.

5 out of 5 average rating, 65 reviews

Falmouth/Woods Hole Charming Cottage By the Sea

Welcome to our Cottage By The Sea Rental located only minutes from the quaint village of Woods Hole, Falmouth and the Martha's Vineyard Ferry. We are located in the perfect setting to relax and enjoy all the area has to offer. Come enjoy The Shining Sea Bike path which is 10.7 miles , Sandy beaches, lively restaurants & local music scene, shopping on historic Main Street, Farmers Markets & more. Your sure to fall in Love with " Ole Cape Cod " when you visit our home and area

4.97 out of 5 average rating, 176 reviews

Apartment 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.

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.

4.93 out of 5 average rating, 41 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!

4.8 out of 5 average rating, 114 reviews

Flat in North Falmouth

Falmouth, Cozy Studio Near Old Silver Beach

This private studio is located in a quiet neighborhood. Located on the second floor, it has A/C, a skylight, Dish TV Amenities include a gazebo. The kitchenette includes a microwave, toaster oven and a Keurig coffee maker. The pool is NOT heated and is open seasonally (July 1 - Labor Day) Close to beaches! Please note there is NO STOVE in the unit.

4.93 out of 5 average rating, 55 reviews

A spacious colonial house is framed by lush green grass and mature trees. The exterior features dark shingles with multiple windows reflecting natural light. A winding driveway leads to the entrance, while a wooden fence provides privacy at the rear.

Home in Edgartown

Beautiful Edgartown 3500 sq ft home, heated pool

Stunning 5 bedroom, 10 room, 3500 square foot colonial in beautiful area. Gourmet kitchen, dining room, living room, den, family room with ping pong. Huge deck, private yard with fire pit and outdoor shower. 30 x 16 x 4 heated in ground pool. Central air. Kayaks, bikes. Seven passenger Toyota Highlander available to rent May- October.