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Vacation 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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Home in Yarmouth Port

4.9 out of 5 average rating, 42 reviews

Winslow Acres [heated] Pool Escape; pool May 15

Pool Open 5/15 Escape to the Cape at this beautifully maintained home with lovely seasonal heated pool (heated spring/fall). Hot tub available all year. Make s'mores and memories year-round at the fire pit table. 4 bedrooms and 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!

Home in Dennis Port

4.89 out of 5 average rating, 57 reviews

Studio vacation home with pool! Walk to the beach!

Adorable condo in the heart of vacationland in Dennis Port! This end studio unit is full of natural light and very comfortable for 2-4 people! The open floor plan offers a large living area with a queen sized bed tucked away in a sleeping corner, and a pull out queen sofa. Step down to the full kitchen which looks out over the backyard space to the shared association pool. All this and right in the middle of the summer fun of Dennis Port and all its activities. The beach is under 1/2 mile away.

Home in East Sandwich

4.92 out of 5 average rating, 64 reviews

Large Home Heated Swimming Pool Private Beach

Perfect for extended-family fun in this stunningly built home (3300 sqft) with 5 bedrooms and 4 bathrooms. First-floor shower. Walk 1000 feet to a private beach with full access rights. Along the beach, you can stroll further east to Sandy Neck Beach. Open kitchen, dining and great rooms are perfect for entertaining! Swim in the ocean or jump right into a beautiful 16x40 heated fiberglass pool with pool lights! Hosted by an extremely experienced host who's committed to making your stay perfect.

Home in Cotuit

4.95 out of 5 average rating, 113 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!

Condo in Brewster

4.97 out of 5 average rating, 177 reviews

Ocean Edge Resort-Pool Access-End Unit-2 bdr/2 bth

2nd floor Ocean Edge end unit condo located in the heart of Brewster with access to OE resort amenities: pools, gyms, tennis courts, as well as access to resort activities (fees apply). Easy access to Cape Cod Rail Trail for bicycles. Scenic route 6A offers arts & crafts galleries 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. A 30 minute ride to Cape Cod National Sea Shore. Welcome to your Happy Place!

Home in Plymouth

4.97 out of 5 average rating, 30 reviews

Getaway with pool

Look no further! This stunning beach house offers everything you need. Situated on a quiet street on Cape Cod Bay, it is very close to area beaches and ponds. The outdoor space is perfect for entertaining and includes lap pool, three decks, patio and fire pit. The downstairs includes living room, family room, bedroom, full bath, eat-in kitchen, and enclosed porch overlooking the backyard. The second floor features 4 more bedrooms, 2 baths, laundry room, and en suite primary bedroom with deck.

Home in Brewster

4.97 out of 5 average rating, 31 reviews

Modern Cape, Private Salt Water Pool, Beaches-Golf

Welcome to your perfect Cape Cod vacation! Nestled in the center of the Cape. Min. to 3 golf courses, 5 ocean beaches, lakes, bike trail etc. Vast serene private 1.5 acres adjacent to conservation land. Lighted Private heated salt water pool, Bocce Court, Putting green, corn hole, hammock, outdoor shower etc. Expansive double deck with awning . Chef’s kitchen & all essential amenities provided. Spacious Beautiful indoor/outdoor dining/entertaining. Pool heat 05/15 to 10/01

Guesthouse in Hyannis Port

4.86 out of 5 average rating, 51 reviews

2 bdrm unit, stairs 4 nights min, pool, no meals

2 bedroom apartment sleeps 4, stairs, shower no tub. We supply all linens. Paper goods only upon arrival. Living/kitchen combo, micro, stove, coffee maker, toaster, iron, hairdryer. No washer dryer, laundromat 1 mile away. Pool,parking, grill, beach chairs available. This is a 2nd floor unit we ask consideration for guests below. No pets, no glass in pool area Walk to beach, town, harbor to catch ferry's Hyannis has tons of unique shops & eateries for all palates. no meals included

Condo in Provincetown

4.92 out of 5 average rating, 39 reviews

Newly Updated Condo w/ Pool - Steps to Boatslip!

This newly updated 2-bed, 1-bath condo, which sleeps 4, is the perfect escape for your Ptown vacation. This first floor condo is only a short walk from Commercial Street and steps to the beach and embodies the best of the Ptown experience! You will love spending time lounging around the lovely pool and exploring all that Commercial Street has to offer! As this property is only steps from the beach, you won't have to venture far to breathe in that relaxing ocean breeze.

Condo in New Seabury

4.98 out of 5 average rating, 130 reviews

Sleep 6 @ New Seabury w/ Pool Access, All Seasons!

Welcome to our beautiful Cape Condo located in The Mews at New Seabury Country Club in Mashpee, MA. Our unit provides access to a private condo association pool a 3 min walk from the unit. Also, we have: -5 min bike/car ride to beach -Central air, wifi, cable, gas grill -Located on Championship Golf Course -Beach chairs, beach towels/toys -New Seabury Village restaurants, mini-golf, bowling, museums -20 min drive to Hy-Line Ferry to Nantucket/Martha's Vineyard

Condo in Provincetown

4.97 out of 5 average rating, 207 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.

Condo in Brewster

4.91 out of 5 average rating, 115 reviews

🌊Cape Escape Nestled in an Amenity Rich Resort🏖

Come stay in this light, bright, clean, newly renovated Cape Escape! From the custom made live edge tables to the incredible natural light, you’re sure to feel calm and comfortable in this beautiful vacation rental. With a three-night minimum and up to a 30-day stay, make it a long weekend getaway or a month of rest and relaxation.

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Popular amenities for Eastham rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in North Eastham

5 out of 5 average rating, 15 reviews

Modern Beach House w/ Heated Pool & Game Room!

Home in East Falmouth

4.93 out of 5 average rating, 15 reviews

Gorgeous Cape Cod Property!

Home in New Seabury

5 out of 5 average rating, 13 reviews

Cape Cod multi-structure family compound with Pool

Home in Mashpee

5 out of 5 average rating, 3 reviews

Mashpee Manor Pool House

Home in Teaticket

4.83 out of 5 average rating, 6 reviews

Charming Home-Pool, Game Room, walk to quiet beach

Home in Harwich

4.79 out of 5 average rating, 14 reviews

4 BD slice of Harwich Heaven

Home in North Falmouth

5 out of 5 average rating, 13 reviews

New Construction Home with Pool in N. Falmouth

Condo rentals with a pool

Condo in Dennis Port

4.78 out of 5 average rating, 58 reviews

Cozy Studio Just Steps Away From the Beach!

Condo in Dennis Port

4.84 out of 5 average rating, 76 reviews

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

Condo in Brewster

4.9 out of 5 average rating, 39 reviews

Ocean Edge: 2 bed/2 bath - Indoor Pools/Gym!

Condo in Brewster

4.98 out of 5 average rating, 56 reviews

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

Condo in Dennis Port

4.84 out of 5 average rating, 58 reviews

Stylish & Modern Studio Condo - Steps to the Beach

Condo in Tisbury

4.91 out of 5 average rating, 47 reviews

Private 3bdrm Condo Tashmoo Woods

Condo in West Dennis

4.84 out of 5 average rating, 51 reviews

Hidden Hideaway

Condo in Tisbury

4.9 out of 5 average rating, 72 reviews

Sunny 2bedroom condo w pool, walk to town

Quick stats about vacation rentals with a pool in Eastham

Total rentals
40 properties
Nightly prices starting at
$90 before taxes and fees
Total number of reviews
1.5K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace

Destinations to explore