
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.

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).

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.

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.

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
House rentals with a pool

Modern Cape Cod home steps to beach; pool access!

Fenced Pool, Fire pit, Outside dining, Coffee bar

Beachside Retreat pool&spa bball court

Sauna, Hot Tub, Walk to Beach -Seaglass Cottage

Salt Winds

West Yarmouth beach house

4 BD slice of Harwich Heaven

Coastal Retreat in Sandwich -Pool Access, Dogs OK!
Apartment rentals with a pool

Cozy Studio Just Steps Away From the Beach!

Luxury Waterfront Getaway

Hidden Hideaway

InnSeason Resorts Surfside

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

Beachside cottage with pool in Provincetown

Our families slice of heaven

Town House for Cape Cod fun, by Bass River.

ShoestringBayHouse, waterfront & pool in Cotuit

Ocean Edge Townhouse/Pool Access

New Construction Home with Pool in N. Falmouth

Bright and Lovely Cottage With Community Pool

Home w/ golf view, salted heat pool, mins to beach
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 € 60 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 & child-friendly amenities 
 - Pet-friendly holiday rentals- Find 10 rentals that welcome pets 
 - Rentals with dedicated workspaces- 10 properties have a dedicated workspace 
 - Wifi availability- 40 of Eastham holiday rentals include wifi access 
 - Popular amenities for guests- Guests love Kitchen, Wifi 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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- Rentals with outdoor seating Eastham
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- Rentals with pools Barnstable County
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- Cape Cod
- Mayflower Beach
- West Dennis Beach
- East Sandwich Beach
- Craigville Beach
- Duxbury Beach
- Onset Beach
- White Horse Beach
- Coast Guard Beach
- Chapin Memorial Beach
- Pinehills Golf Club
- Minot Beach
- Nauset Beach
- Lighthouse Beach
- Inman Road Beach
- Town Neck Beach
- Ellis Landing Beach
- Nickerson State Park
- New Silver Beach
- Falmouth Beach
- Cape Cod Inflatable Park
- Scusset Beach
- Peggotty Beach
- Cahoon Hollow Beach
