Vacation rentals with a pool in Eastham

5 out of 5 average rating, 8 reviews

A spacious backyard is featured, highlighting a refreshing oval pool surrounded by a textured patio. Lounge chairs are positioned for relaxation under the sun. Lush greenery and trees provide a natural border, while a well-kept lawn enhances the inviting outdoor space.

Home in Chatham

Heated Pool. Hot Tub. Game Room. Beach Nearby!

Welcome to The Tide Watch - our luxurious retreat, perfect for families or a group of friends! This stunning home features high-end furniture, a pool, hot tub & games including ping pong & air hockey. With kid-friendly amenities, everyone will feel at home. Relax, play & create unforgettable memories in this upscale oasis designed for fun & relaxation! Walk to small neighborhood beach 3 min drive to Jacknife Beach 6 min drive to downtown Chatham Experience Chatham with us & Learn More Below!

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!

4.97 out of 5 average rating, 195 reviews

A welcoming entryway is observed, featuring a rustic 'WELCOME' sign on the wall. Light wood flooring extends into a cozy living and dining space, illuminated by natural light. A dining table is visible in the background, surrounded by comfortable chairs.

Condo in Brewster

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!

4.98 out of 5 average rating, 42 reviews

A spacious heated saltwater pool is surrounded by a large deck featuring colorful lounge chairs and an umbrella. The attractive two-story house stands in the background, framed by lush greenery and trees, creating a peaceful outdoor setting.

Home in Brewster

Modern Cape, Private Salt Water Pool, Beaches-Golf

Welcome to your perfect Cape Cod vacation! Nestled in the center of the Cape. Min. to 3 golf courses, 5 ocean beaches, lakes, bike trail etc. Vast serene private 1.5 acres adjacent to conservation land. Lighted Private heated salt water pool Mid May to Early Oct. ,Bocce Court, Putting green, corn hole, hammock, outdoor shower etc. Expansive double deck with awning . All essential amenities provided. Spacious Beautiful indoor/outdoor dining/entertaining. 2026 Pool season 05/14- 10/05

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.

4.91 out of 5 average rating, 115 reviews

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

The Sea Salt Studio - Steps to the Beach!

Gorgeous studio (Unit #1) 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 and cable/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.

5 out of 5 average rating, 6 reviews

Home in Chatham

Luxury Home w/ Salt Water Pool Overlooking Ocean

Welcome to your dream Cape Cod getaway! Our brand-new, fully renovated 4-bedroom, 5-bath luxury home offers breathtaking views of Buck’s Creek and Nantucket Sound, creating the perfect backdrop for your vacation. Inside, you'll find a stunning cathedral-ceiling living room designed for relaxation and gathering. The chef’s kitchen features a massive 15-foot eat-in island, perfect for family breakfasts or evening cocktails. Each of the spacious bedrooms offers comfort and privacy.

4.93 out of 5 average rating, 123 reviews

Home in North Truro

15% OFF 25x42 heated pool, pets, ADA, EV, 4ensuite

-15% OFF until April 2nd 2026. 25X42 heated pool(April 1-Nov 30) -SEASON- June 20-Sept 4th (7) night min. SAT.-SAT. ONLY -OFF SEASON- April 18-June 20 and Sept4th-January 4 (2) night min. -NO BALLOONS, PARTY, EVENTS, BRIDAL, WEDDING RECEPTIONS, MAX 12 for pool/ dinners. Extra guests=immediate eviction. -We encourage you to comp our home to others w/ same amenities/local to know market rates of Truro. If you find a home of lesser value we will adjust accordingly.

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.

A scenic view showcasing the bay with gently rippling waters and distant land on the horizon. The foreground features coastal vegetation, including pines and shrubs, along a wooden pathway leading toward the beach. Nearby, a stop sign indicates road access.

4.97 out of 5 average rating, 238 reviews

P-Town Beach Beauty on the Bay. Water View!

Beautiful Water View East End 2 bedroom condo across the street from the beach on the bay. Just cross the road and take the association maintained steps down to the beach. This beach boasts a nice tidal swing where you can walk out in the shallows during low tide. The condo is in the perfect East End location, combining closeness to the center of town, with your own beach and not having the noise and parking issues of downtown Provincetown.

4.9 out of 5 average rating, 140 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.

4.97 out of 5 average rating, 164 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).

Popular amenities for Eastham rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 23 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!

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!

4.72 out of 5 average rating, 39 reviews

A serene backyard setting features a private pool surrounded by a spacious patio. A sunbathing chair and a BBQ grill are positioned nearby, with a house showcasing large windows that invite natural light. Lush greenery frames the area, providing a sense of tranquility.

Home in Dennis

House on Cape Cod with pool close to beach

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, 25 reviews

An aerial view of a spacious backyard features a heated pool surrounded by a grey stone patio. Lounge chairs and umbrellas are positioned around the pool. The house showcases multiple large windows and a deck, with green grass and trees creating a private setting.

Home in Plymouth

Mansion with Heated Pool Near Ocean

4.85 out of 5 average rating, 65 reviews

A charming Cape-style house is surrounded by lush green grass, featuring a well-maintained front yard adorned with flower beds and small American flags. The entrance is highlighted by a decorative door with a wreath, framed by neatly arranged bushes. A single-car garage is visible on the right.

Home in Mashpee

Sunny Cape w/Private Pool, Steps to Private Lake

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

Condo rentals with a pool

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

4.75 out of 5 average rating, 16 reviews

A living area features a light-colored sofa and an armchair beside a wooden table. A bookshelf with nautical decor and a lamp provides soft lighting. Sliding glass doors open to a private deck, offering views of greenery beyond.

Condo in Truro

Unit #6 - 2nd Floor- Efficiency Studio, with A/C

4.96 out of 5 average rating, 90 reviews

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

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

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

The open living space features large windows providing direct views of Cape Cod Bay. A light-colored sectional sofa is positioned to maximize views, while a ceiling fan offers air circulation. The room's modern decor is complemented by natural light streaming through the windows.

4.85 out of 5 average rating, 39 reviews

Spectacular Waterfront Condo

A scenic view of a coastline is presented, showcasing calm blue waters meeting a sandy beach. Rocky outcrops create a natural border, with a distant lighthouse visible along the horizon. The sky exhibits clear blue tones, enhancing the overall serene landscape.

4.89 out of 5 average rating, 109 reviews

Bright Beach Condo • Walk to Sand & Shops

A modern living area features a vibrant orange sectional sofa complemented by light walls and hardwood flooring. A glass coffee table sits centrally, while a small dining area with white chairs is visible. Artwork adorns the walls, contributing to a welcoming ambiance.

4.94 out of 5 average rating, 48 reviews

Newly Updated Condo w/ Pool - Steps to Boatslip!

5 out of 5 average rating, 87 reviews

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.

Condo in Brewster

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

Other vacation rentals with a pool

Vacation home in South Yarmouth

A cozy bedroom area is highlighted by a spacious bed adorned with decorative pillows and a colorful bedspread. Nightstands with lamps are positioned on either side, while a seating area and dining table are visible in the background, providing a seamless connection to the living space.

4.88 out of 5 average rating, 16 reviews

Oceanfront location with amenities

4.9 out of 5 average rating, 31 reviews

A charming cottage features shingle siding and a well-maintained exterior. A large deck with a grill is visible at the front. Surrounding greenery and a stone pathway lead to the entrance, which is framed by large windows allowing natural light into the interior.

Cottage in North Truro

Beachside cottage with pool in Provincetown

5 out of 5 average rating, 40 reviews

Camper/RV in Wellfleet

Seasonal 27’ Retro Glamping Steps From Bike Trail

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

4.75 out of 5 average rating, 4 reviews

1BR Condo w/ Balcony in Mashpee, MA

4.93 out of 5 average rating, 46 reviews

The exterior of the beach house is presented, featuring multiple stories and a light grey facade. A lap pool is nestled beside a spacious patio, equipped with lounge chairs and an umbrella. Lush greenery surrounds the property, enhancing the serene environment.

Home in Plymouth

Getaway with pool

4.9 out of 5 average rating, 87 reviews

The exterior of a contemporary cottage is seen, featuring a light-colored wooden facade and a circular window. An American flag is displayed proudly from the front. A fenced yard surrounds the property, complemented by greenery and a gravel pathway.

Cottage in Dennis Port

Bright and Lovely Cottage With Community Pool

5 out of 5 average rating, 7 reviews

A paved outdoor seating area is visible with several round tables and chairs arranged to provide views of the water at sunset. The sky features warm hues of orange and purple as the sun dips below the horizon, with the ocean beyond and neighboring houses in the background.

Apartment in Dennis Port

Steps to the Beach & Heated Pool!