
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.

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!

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!

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.

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

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.

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!

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.

Stunning Cape Home - Inground Pool, 5 Min To Beach
Stunning in-ground pool. Just 5 minutes from Craigville, Dowses and Covell's Beach! Perfect for mid-size groups or families, this home sleeps 8 and boasts a dreamy, private, fenced-in backyard w/ a, pool house w/ TV & bar, outdoor shower, and cozy patios. Complete w/ all your beach essentials. Conveniently located, we're 13 minutes from Mashpee Commons and 10 minutes from local grocery stores, local bakeries& restaurants. Central to all the Cape has to offer!

Paradise Palm - #4
Come and stay at this classic cape cod oasis directly across the street from Allan Harbor. Tucked in a quiet, family friendly neighborhood. This space has a private entrance with a table for 2, where you can sit, relax and enjoy the fresh air off the comfort of your room. Enjoy easy access to popular shops, restaurants, beaches and a ferry to Nantucket from this cozy getaway. Easy self check in with free parking for 1 car. *Pack n' Play upon request

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.

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.

Cute Cottage Near Beach & Main Street 3BR/3BA (15)
Stay at a charming 3-Bedroom cottage in a beautiful setting within walking distance to Cape Cod's warm sandy beaches and Main Street Hyannis. Captain Gosnold Village is ideally located within a short walk from three of the Cape's best beaches and nestled between picturesque Hyannis Port and the vibrant atmosphere of Hyannis Harbor with its island ferries, sightseeing and fishing charters.
Popular amenities for Eastham rentals with a pool
House rentals with a pool

Family Fun- Games, Pool & HotTub, Dogs ok! Slps 10

Fenced Pool, Fire pit, Outside dining, Coffee bar

Beachside Retreat pool&spa bball court

Sauna, Hot Tub, Walk to Beach -Seaglass Cottage

Mansion with Heated Pool Near Ocean

Salt Winds

ShoestringBayHouse, waterfront & pool in Cotuit

4 BD slice of Harwich Heaven
Condo rentals with a pool

Cozy Studio Just Steps Away From the Beach!

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

Hidden Hideaway

Spectacular Waterfront Condo

Bright Beach Condo • Walk to Sand & Shops

Newly Updated Condo w/ Pool - Steps to Boatslip!

Condo in Falmouth MA

Oct + Nov Discount | Central | Private Balcony
Other holiday rentals with a pool

Modern Cape Cod home steps to beach; pool access!

Beautiful Mashpee Home with Pool

Beachside cottage with pool in Provincetown

Our families slice of heaven

New Construction Home with Pool in N. Falmouth

Home w/ golf view, salted heat pool, mins to beach

Steps to the Beach & Heated Pool!

Renovated ranch with pool access
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 $121 NZD 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!
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