Holiday rentals with a pool in Chatham

5 out of 5 average rating, 9 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

Pool. Hot Tub. Game Room. Walk to Beach. Luxury!

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!

4.92 out of 5 average rating, 49 reviews

A spacious outdoor area is highlighted by a seasonal heated pool surrounded by a wooden deck. Multiple blue lounge chairs are arranged around the pool, and a fire pit table is situated at the center. A large checkers board and garden beds add to the inviting atmosphere.

Home in Yarmouth Port

Winslow Acres [heated] Pool Escape; pool May-Oct

Pool Closes 10/14/25; reopens mid-may for 2026 season. Hot tub open year-round Escape to the Cape at this beautifully maintained home with lovely seasonal heated pool (heated spring/fall). Hot tub available all year. 4 bedrooms, 2.5 baths (2 showers) plus an outside shower May through October. Plenty of room for up to 8 people - sorry, no parties - (plus pets - fee applies)! Only 3 miles to beaches. The ferry to Nantucket and Martha's Vineyard is not far, and a great addition to any Cape trip!

5 out of 5 average rating, 101 reviews

The balcony offers a view of the lush golf course, framed by trees and natural landscape. A round table with two high stools sits center stage, accompanied by a candle, creating a peaceful outdoor setting for relaxation.

Apartment in Brewster

Ocean Edge Resort-Pool Access-CentralAC-2 bdr/2bth

Modern 2nd floor 2 bed/2 full bath Ocean Edge condo located in the heart of Brewster with balcony overlooking the resort golf course. Access to OE resort amenities (additional fees apply). Easy access to Cape Cod Rail Trail. Scenic route 6A offers arts & crafts galleries, coffee places 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. 15 minute walk to Ellis Landing Beach, great sunsets! Central A/C and heat

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 6/20-9/15/26. The reviews tell all!

4.98 out of 5 average rating, 42 reviews

Home in Brewster

Modern Cape, Private Heated Pool, Beach, Golf

Welcome to your perfect vacation/reunion in the center of the Cape. Min. to 3 golf courses, 5 ocean beaches, lakes, park, trails. Bright modern quality home available year-round. Vast serene private 1.5 acres adjacent to conservation land. Lighted Private heated saltwater pool Mid May to End Sept. Bocce Court, Putting green, Corn hole, Hammock, Outdoor shower, AC. Expansive double deck with awning. Beautiful indoor/outdoor dining/entertaining. All essentials provided. 7+ free parking.

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.

Flat 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.

Apartment in Dennis Port

Sea Salt Studio - Steps to Glendon Rd Beach

Funky studio (Unit #1) only 175 yards from a white sand beach on Nantucket Sound. 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.

4.95 out of 5 average rating, 57 reviews

A spacious wooden deck is surrounded by trees, offering a serene view of the natural landscape. A small round table with drinks is set between two folding chairs. A gas grill is positioned against a wooden railing, with sunlight filtering through the foliage.

Flat in Barnstable

Studio Apartment

Private Studio Apt on lower level of owner occupied House.Private deck overlooking Pond. Queen bed, single sofabed/and small sleeping loft. Very comfortable for 2 people but can sleep up to 4. Kitchenette w/dinnerware and cookware. Coffee maker, fridge, microwave, toaster oven, outside gas grill. Private bath/shower. TV, WiFi, A/C. Pond access, SUP, kayaks. Pool/hot tub on Main House level available for use on request. Sunrise view. Golfcourses, shopping, restaurants, beaches nearby.

A view overlooking a well-maintained pool surrounded by green grass, with beach access visible in the distance. The landscape features a mix of trees and charming houses, set against a clear blue sky and tranquil water.

4.9 out of 5 average rating, 323 reviews

Ocean Side, Amazing View, close to town/beach, Spa

PRICING IS FOR 2 GUESTS, 1 BEDROOM, 1 BATH ONLY, can add additional bed/bath for a fee, YOU WILL HAVE THE HOUSE TO YOURSELF. We only use this listing to fill gaps when the larger listing isn't rented & will decline ALL WEEKENDS, HOLIDAYS, PEAK times and will only accept mid-week, non summer/holidays. Please read additional info. OCEAN FRONT, HISTORIC SUMMER COTTAGE, AMAZING VIEWS, GREAT LOCATION, less than 1 mile walk to town and beach. Hot tub, fireplace, stocked kitchen, fresh linens.

5 out of 5 average rating, 33 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. 3 night Thursday to Sunday minimum in June.

4.93 out of 5 average rating, 100 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.

4.9 out of 5 average rating, 144 reviews

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.

Flat in Hyannis Port

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.

Popular amenities for Chatham rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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

A saltwater pool is set within a stone patio area, surrounded by lush greenery. Lounge chairs and a shaded table with a red umbrella offer comfortable seating options. The serene view of Morey Pond is visible beyond the pool, framed by trees under a clear blue sky.

4.97 out of 5 average rating, 65 reviews

Our families slice of heaven

4.97 out of 5 average rating, 29 reviews

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.

Home in New Seabury

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

4.74 out of 5 average rating, 69 reviews

Spacious Retreat With Pool, Game Room & Fireplace

4.85 out of 5 average rating, 66 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

4.94 out of 5 average rating, 71 reviews

A bright studio unit features a queen-sized bed with a comfortable pull-out sofa nearby. Natural light floods the space through large windows. A small dining table with two chairs is positioned next to the seating area, providing a functional living space.

Home in Dennis Port

Walk to the beach or sit poolside! Updated studio!

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.

4.94 out of 5 average rating, 48 reviews

Getaway with pool

4.95 out of 5 average rating, 60 reviews

A view from the deck reveals a well-maintained pool area surrounded by lounge chairs and umbrellas. Adjacent to the pool is a tennis court, framed by greenery, providing a serene backdrop. The water sparkles under a clear blue sky, inviting relaxation.

Home in East Falmouth

Family + Dog Retreat | Fenced Yard + Pool + Beach

Apartment rentals with a pool

4.82 out of 5 average rating, 74 reviews

A spacious sleeping area features a large bed with neutral bedding and colorful accent pillows. A TV is mounted on the wall. Natural light filters through a sliding glass door, which opens to an outdoor area with a small table and chairs.

Apartment in Dennis Port

Cozy Studio Just Steps Away From the Beach!

4.93 out of 5 average rating, 44 reviews

A light-filled living area features a cozy sofa layered with a soft throw, accompanied by a stylish coffee table. The calming wall art depicts ocean waves, while lamps provide additional lighting. A door leads outside, and a chair adds a pop of color.

Apartment in West Dennis

1BR 2nd Floor Condo with pool

4.84 out of 5 average rating, 87 reviews

The spacious living area features a queen-sized bed and a comfortable sofa. A dining table with two chairs sits near the window, allowing natural light to brighten the room. Simple decor includes star-shaped wall accents, enhancing the relaxed coastal ambiance.

Apartment in Dennis Port

Comfy Cape Escape! Spacious, Cozy, Close to Beach!

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.

Apartment in Truro

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

4.85 out of 5 average rating, 55 reviews

Apartment in Brewster

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

4.96 out of 5 average rating, 97 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.

Apartment 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.

Apartment in West Dennis

Hidden Hideaway

4.97 out of 5 average rating, 60 reviews

A serene pool area is visible, featuring clear blue water under a sunny sky. Poolside loungers are arranged for relaxation, while the two-story condo building with balconies lines the background. Lush greenery and trees enhance the outdoor space.

Apartment in West Dennis

Mary's Cape Escape

Other holiday rentals with a pool

4.8 out of 5 average rating, 5 reviews

A heated pool is surrounded by a spacious stone patio, featuring several lounge chairs with blue cushions. A black fence encloses the area, overlooking a lush green yard with trees in the background under a clear blue sky.

Home in Chatham

Family friendly luxury home with heated pool & spa

5 out of 5 average rating, 23 reviews

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

Home in Falmouth ~ 5 min drive to beach

4.89 out of 5 average rating, 57 reviews

A modern kitchen is displayed, featuring stainless steel appliances, sleek cabinetry, and contemporary lighting along the countertops. A dining table with high-backed stools is positioned near the kitchen, with a decorative vase of yellow flowers adding a touch of color.

Flat in Dennis

Pool Condo Near Mayflower Beach Sleeps 4

4.82 out of 5 average rating, 34 reviews

The exterior showcases a contemporary home with a blend of stone and siding elements. Solar panels are visible on the roof, and a circular driveway leads to a welcoming entrance with double doors. Surrounding greenery enhances the property’s serene setting.

Home in Sagamore

Sagamore Manor | Pool | Hot Tub | 5min to Beach!

5 out of 5 average rating, 6 reviews

A welcoming exterior view of a modern house is presented, featuring a well-maintained path leading to the entrance. Flanking the walkway, neat landscaping includes flowering bushes and a lush green lawn. A bright sun casts a soft glow over the façade, enhancing the inviting atmosphere.

Home in Mashpee

Mashpee Manor Pool House

4.82 out of 5 average rating, 11 reviews

A fenced backyard with a sparkling pool is surrounded by a manicured lawn and blooming shrubbery. Lounge chairs are positioned near the water, inviting relaxation. The home features a two-story design, with windows overlooking the outdoor space and wooded area in the background.

Home in Falmouth

Overlook Poolside Getaway Heated Pool (May - Oct 2

4.82 out of 5 average rating, 17 reviews

A heated saltwater pool glistens under the sun, surrounded by a spacious paver patio. The fenced backyard provides privacy, while a light-colored house with a deck offers a welcoming ambiance. Lush trees stand in the background, enhancing the serene outdoor space.

Home in Barnstable

Centerville Oasis, Heated Saltwater Pool!