Holiday rentals with a pool in Eastham

5.0 out of 5 average rating, 13 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!

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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.

5.0 out of 5 average rating, 109 reviews

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

FamilyLocationTV

4.98 out of 5 average rating, 50 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, AC, enjoyable year-round. Vast serene private 1.5 acres adjacent to conservation land. Pool heated Memorial day weekend- last Sunday of 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.

LocationFamilyTV

4.92 out of 5 average rating, 127 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

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.

FamilyLocationWalkability

4.93 out of 5 average rating, 40 reviews

The backyard features an inground pool illuminated at night, surrounded by wooden decking. Nearby, a shed with white shutters enhances the outdoor space, while lush greenery provides a serene backdrop.

Home in Orleans

5-bedroom Cape with a pool and yard games.

Five-bedroom and three-bath Cape style home with large fenced backyard and an inground pool. Various yard games are available - outdoor ping pong table and corn toss. Short distance to Pleasant Bay, freshwater ponds, and the ocean. Approximately five miles from downtown Chatham and Orleans Center. A variety of local shops, and restaurants, and catch the Cape Cod Baseball under the lights just minutes away. (Our pool is not heated - the opening and closing is weather dependent).

LocationFamilyGetting around

5.0 out of 5 average rating, 32 reviews

Bright and airy living space is highlighted by a spiral staircase leading to an open loft. A plush light grey sofa faces a coffee table on a woven area rug, while a dining table and chairs are visible in the background. Modern kitchen cabinetry offers a sleek contrast.

Apartment in Brewster

Townhouse at Ocean Edge 2B/2B + Loft

Experience resort-style living at its finest! Tucked away just a 10-minute drive to the beach, this delightful townhouse offers the perfect blend of comfort and convenience. With two bedrooms, two baths, and an additional cozy loft space, there's ample room for relaxation. Enjoy lounging on the patio, take a refreshing dip in one of the resort pools (for an additional fee paid directly to Ocean Edge) or head to the beach for some sun and surf. Your ultimate getaway awaits!

FamilyLocationBackyard

4.9 out of 5 average rating, 10 reviews

A distinctive A-frame cottage is situated among tall trees, surrounded by natural greenery. The entrance features a wooden deck with a picnic table and two chairs, inviting relaxation in the outdoors. Clear skies provide ample sunlight, enhancing the cottage's inviting atmosphere.

Cottage in Wellfleet

The Cottages at Even'tide Resort - Seagull

Seagull cottage is one of 8 cottages located at the Even'tide Resort. Where else on Cape Cod can you rent a private cottage and enjoy a huge heated indoor pool and direct access to a 22 mile paved bike path? A 1 mile hike through the woods takes you to Marconi National Seashore beach. You have access to all the amenities at the motel including ping pong, billiards, 5 hole mini golf, shuffleboard, corn hole, fitness room, playground, basketball court, and coin op laundry.

LocationFamilyBeach

4.89 out of 5 average rating, 107 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.

FamilyValueHospitality

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.

4.9 out of 5 average rating, 157 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.

LocationFamilyPool

5.0 out of 5 average rating, 6 reviews

Apartment in Brewster

Two Bedroom Condo in Ocean Edge Resort

Experience the perfect blend of relaxation and recreation in this updated 2-bed, 2-bath condo at Ocean Edge Resort, Brewster. Near the Arbor pool and Linx Golf Club, it’s an ideal hub. The primary suite features a queen bed, golf views, and a renovated ensuite. The second bedroom features an oversized bunk (full + 2 twins). Includes an equipped kitchen, in-unit laundry, and a covered patio with fairway views. Near Brewster’s beautiful beaches, shops, and dining.

LocationFamilyView

4.87 out of 5 average rating, 67 reviews

A charming cottage exterior is showcased, featuring natural wood shingles and red shutters. A bright orange door provides a welcoming entrance. Lush green leaves frame the image, highlighting the serene surroundings of the property against a clear sky.

Cottage in Wellfleet

Wellfleet~Beautiful One Day Perfect The Next

Are you looking for the perfect getaway in charming Wellfleet? This two-bedroom cottage is located in a private, detached cottage village. Enjoy the beautiful SEASONAL in-ground pool (OPENS July 4th & CLOSES LABOR DAY) and a welcoming family-friendly atmosphere. The cottage is centrally located with a five-minute drive to both bay and ocean side beaches, freshwater kettle ponds, Wellfleet center, and the rail trail!

FamilyLocationQuiet

4.88 out of 5 average rating, 120 reviews

The exterior of the Cape Cod cottage is shown, featuring a light-colored siding and a unique turret-like structure. Lush green landscaping surrounds the home, which is set back from a gently curved pathway. Tall trees provide natural shade in the area.

Townhouse in Brewster

Ocean Edge Cape House with Beach, Pool, and AC

Your dream Cape Cod getaway awaits! This classic Cape Cod cottage is nestled in the heart of Brewster, offering a perfect blend of comfort, relaxation, and outdoor adventure. With access to a private beach, resort-style amenities, and iconic local attractions, this is the ultimate retreat for families, couples, or groups looking to experience the best of the Cape.

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Popular amenities for Eastham rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.96 out of 5 average rating, 140 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

FamilyLocationComfort

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

LocationFamilyCleanliness

4.96 out of 5 average rating, 27 reviews

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.

Home in Barnstable

Beach Pass Included! Brand New Spa! Central AC!

LocationFamilyIndoor spaces

4.73 out of 5 average rating, 40 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

LocationValueBiking

4.81 out of 5 average rating, 42 reviews

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.

Home in Barnstable

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

LocationValueAmenities

4.94 out of 5 average rating, 48 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

FamilyLocationGetting around

Home in Barnstable County

A bright dining area is illuminated by natural light from large windows, offering views of the waterfront. A small table is surrounded by four blue stools, while a vase of flowers adds a touch of color. A comfortable gray sofa is positioned nearby.

4.91 out of 5 average rating, 33 reviews

Waterfront Bass River Jolly Captain

FamilyLocationQuiet

5.0 out of 5 average rating, 7 reviews

Home in East Dennis

Charming Cape Escape with Pool, Hot Tub & Fire Pit

FamilyLocationHot tub

Condo rentals with a pool

4.97 out of 5 average rating, 178 reviews

Condo in New Seabury

New Seabury Cape Condo | Pool & Beach Escape

LocationValueCheckout

4.97 out of 5 average rating, 256 reviews

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.

Condo in Provincetown

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

LocationFamilyComfort

4.91 out of 5 average rating, 22 reviews

Bright Cape Condo in Ocean Edge

LocationValueView

4.93 out of 5 average rating, 46 reviews

A spacious studio layout features two queen-size beds dressed in crisp white linens, complemented by a cozy seating area with a blue armchair. A dining table with four chairs sits nearby, and large windows offer views of the private balcony and outdoor surroundings.

Condo in Truro

Unit #48 - 2nd Floor Deluxe Studio with A/C

FamilyLocationHiking

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.

5.0 out of 5 average rating, 95 reviews

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

LocationValueBiking

4.85 out of 5 average rating, 68 reviews

Resort Pools & Golf Views · Walk to Bay Beaches

ValueFamilyHiking

4.95 out of 5 average rating, 65 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.

Condo in West Dennis

Mary's Cape Escape

LocationValueBathroom

4.96 out of 5 average rating, 77 reviews

Condo in West Dennis

Steps from Bass River Marina · Private Balcony

LocationFamilyGetting around

Other holiday rentals with a pool

4.88 out of 5 average rating, 42 reviews

A light-filled living area features a beige sofa and a matching loveseat, accented by navy and white decorative pillows. A round wooden coffee table sits in the center, surrounded by a patterned area rug. Sliding glass doors provide access to the outdoor space.

Townhouse in Brewster

Ocean Edge Townhouse/Pool Access

FamilyValueWi-Fi

4.85 out of 5 average rating, 13 reviews

Apartment in Dennis Port

Dennis Deluxe King Room | Full Studio w/ Kitchenet

ValueFamilyQuiet

4.76 out of 5 average rating, 38 reviews

A bright bedroom features blue walls and a floral accent wall. A spacious bed with a textured quilt is positioned prominently. Natural light enters through a skylight, and a flat-screen TV is mounted on the wall. Storage units in warm wood tones complement the space.

Apartment in Dennis Port

King Bed Suite (Pet Friendly) in a great location

LocationValueQuiet

4.96 out of 5 average rating, 28 reviews

Cottage in Yarmouth

Cottage at the Escape Inn

FamilyLocationCleanliness

4.88 out of 5 average rating, 41 reviews

A compact studio layout features a spacious bed adorned with neutral tones and decorative pillows. A modern kitchen area showcases stainless steel appliances and cabinetry, with a light tile floor enhancing the space. Natural light filters through sheer curtains, creating a bright and airy environment.

Home in Dennis Port

Beachwalk cozy studio with pool!

LocationPoolComfort

4.89 out of 5 average rating, 63 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.

Apartment in Dennis

Breezy Pool Retreat Near Mayflower Beach

FamilyLocationQuiet

Guest suite in Harwich Port

A bright, airy living space features a comfortable couch, accompanied by decorative pillows. Natural light enters through a skylight and glass doors, which open to an outdoor area. A small console table holds decorative items, adding to the inviting ambiance.

4.99 out of 5 average rating, 71 reviews

The Captain's Quarters Suite - #10

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