Holiday rentals with a pool in Eastham

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Eastham

Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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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
4.71 out of 5 average rating, 28 reviews

Cape Cod Condo,Walk to Beach, near Nantucket Ferry

Enjoy your next beach vacation at this charming cottagecore-style condo located in the quintessential seaside town of Harwich Port, just a short walk to nearby Wyndemere Bluffs beach.This delightful beach cottage includes 1 bedroom, 1 bathroom, with an additional queen pull out to accommodate 2-4 guests. Grill out on the porch, take a stroll down Main St for ice cream or lobster rolls, or take a dip in the private community pool (steps from your front door)!Nantucket ferry 1 mile down the road!

Guest favourite
The living room features two comfortable sofas adorned with colorful cushions, situated around a wooden coffee table on a vibrant area rug. Natural light fills the space, highlighting the dining area and fully equipped kitchen visible in the background.
Condo in Brewster
4.85 out of 5 average rating, 55 reviews

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

Welcome to our spacious and well-appointed 2-bed, 2-bath condo with a private patio overlooking the golf course at Ocean Edge Resort. Access to resort amenities (additional fees apply) and restaurants. We acquired this condo in 2023 and are excited to host you! Perfect for families with kids or a group of friends! You will be a short walk from Ellis Landing Beach and CC Rail Trail and a short car ride away from 10 Brewster bay beaches. Route 6A offers shops, restaurants, art galleries and more!

Guest favourite
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
4.96 out of 5 average rating, 90 reviews

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

Enjoy this 1,000 SF, 2 bed, 2 full new marle tile bathrooms, 2 showers, at Ocean Edge, right in the middle of the golf course. This Airbnb is a full member of the Ocean Edge Resort and allows you access to Ocean Edge golf, and free resort access included up to 6 guests to swimming pools, tennis, gym & pickleball. No one lives here, it is absent of personal items. From the moment you enter, you will know that you have made a great choice and that your time here will be above your expectations.

Top Guest favourite
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.
Condo in Brewster
5 out of 5 average rating, 100 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

Top Guest favourite
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
5 out of 5 average rating, 87 reviews

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

Recently renovated end unit townhouse located in the heart of The OE Villages. Beautiful views towards the golf course, and southern exposure with lots of natural light, A/C, W/D and private patio with Weber grill and outdoor furniture. Sports Membership so Guest passes are available for purchase at Linx for use of pools, hot tubs and gyms. Additional costs for use of courts may apply. Bike rail trail, Ice cream store, great restaurants, coffee, beaches and Kayak/Bike rentals are all close by.

Top Guest favourite
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
4.95 out of 5 average rating, 128 reviews

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!

Top Guest favourite
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
4.98 out of 5 average rating, 105 reviews

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.

Guest favourite
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
4.91 out of 5 average rating, 33 reviews

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).

Top Guest favourite
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
5 out of 5 average rating, 32 reviews

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.

Guest favourite
A pool area features a rectangular swimming pool surrounded by a stone patio. Loungers and two shaded areas offer seating options. The home in the background is two stories with white siding, and leafy trees provide a pleasant backdrop.
Home in Chatham
4.97 out of 5 average rating, 60 reviews

Luxury Beach Barn with Pool, Hot Tub & Sauna

Experience the ultimate getaway at this stunning 7-bedroom retreat, just a mile from Cape Cod’s pristine beaches. Enjoy a top-rated gourmet kitchen, a charming renovated barn, and a Catina Pool Bar perfect for poolside relaxation. With a sparkling pool and a soothing sauna, this home offers the perfect blend of elegance and comfort. This property is ideal for family vacations, group getaways, and special celebrations. Book now No events allowed.

Top Guest favourite
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
4.97 out of 5 average rating, 237 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.

Guest favourite
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
4.9 out of 5 average rating, 139 reviews

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.

Popular amenities for Eastham rentals with a pool

Quick stats about holiday rentals with a pool in Eastham

  • Total holiday rentals

    Explore 40 holiday rentals in Eastham

  • Nightly prices starting at

    Eastham holiday rentals start at $107 AUD per night before taxes and fees

  • Verified guest reviews

    Over 1,290 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Eastham holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Eastham rentals

  • 4.8 Average rating

    Eastham stays are highly rated by guests—averaging 4.8 out of 5!