Vacation rentals with a pool in Eastham

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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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Guest favorite

Condo in Mashpee

4.97 out of 5 average rating, 101 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 -2 bicycles available for use -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

Oct 29 – Nov 5

ﺩ.ﺇ876 per night

Guest favorite

Condo in Brewster

4.97 out of 5 average rating, 158 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!

Nov 19 – 26

ﺩ.ﺇ1,051 per night

Guest favorite

Apartment in Wellfleet

4.97 out of 5 average rating, 34 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.

Apr 19 – 26

ﺩ.ﺇ558 per night

Guest favorite

Condo in Dennis

4.93 out of 5 average rating, 28 reviews

Stylish & Modern Studio Condo - Steps to the Beach

Stay in a renovated modern, cozy studio style condo with walking distance to Glendon Beach. This stylish airy & bright poolside retreat is perfect for couples and solo travelers. A slider door offers direct access to the shared pool area. The kitchenette features quartz counters, a sink, refrigerator, 2-burner cooktop, and a microwave. Enjoy a restful night's sleep with a memory foam mattress and black-out curtains. The home also has a 24" Roku Smart TV for you to enjoy your favorite shows.

Oct 25 – Nov 1

ﺩ.ﺇ565 per night

Guest favorite

Condo in Brewster

4.84 out of 5 average rating, 31 reviews

Golf Course Views and Pools

Enjoy your Cape Cod vacation in Brewster, MA by staying in a cozy and bright condo unit. The unit itself is overlooking hole #12 on a beautiful golf course, owned by well-known Ocean Edge Resort. Lined with plenty of trees there is privacy and quietness, perfect for sitting on the outdoor balcony underneath the stars with a relaxing glass of wine. Part of a country club, you have access to multiple indoor/outdoor swimming pools, gym, saunas, hot tubs, golf course, and restaurants for a fee.

May 22 – 29

ﺩ.ﺇ553 per night

Guest favorite

Cottage in Sandwich

4.92 out of 5 average rating, 130 reviews

Blue Anchor Cottage - private hot tub getaway!

This newly renovated cottage is an amenity-filled launching point to explore all of Cape Cod! Just 0.4miles to the beach and with our own salt water pool, you’ll be able to fully enjoy the Cape's most historic town. Some of our favorites nearby: 2min- your local coffee shop 2min- great fish tacos + bar 2min- nice conservation area hike 2min- local convenience store 7min- downtown Sandwich 7min- golf course 9min- Sandwich Boardwalk 10min- Heritage Museums & Gardens 22min- Cape Cod Rail Trail

Oct 14 – 21

ﺩ.ﺇ1,297 per night

Guest favorite

Camper/RV in Wellfleet

5.0 out of 5 average rating, 20 reviews

Seasonal 27’ Retro Glamping Steps From Bike Trail

A SECLUDED WELLFLEET LOCATION, STEPS FROM BIKE PATH WITH DELIGHTFUL AMENITIES. This 27’ Camper with many upgrades, and shared 18X30 pool is located in a peaceful setting on private property (with Host’s Home set back ) just steps from the Cape Cod BikeTrail and Hiking Trails. Location will especially appeal to Avid Cyclists, as well as Beach Goers and people looking to enjoy activities in beautiful Wellfleet. The Atlantic Ocean Beaches are car or bike accessible 5-10 minutes away.

May 31 – Jun 7

ﺩ.ﺇ723 per night

Guest favorite

Apartment in Dennis

4.88 out of 5 average rating, 16 reviews

Pool condo in Dennis Village, 4 mins to Mayflower

Relax in this calm, stylish, new, fully equipped 1 BR condo. “Cape Storia d’ Amore” is 4 mins from Mayflower in the heart of Dennis Village. Located less than 5 minutes from The Merc, Scargo, Oliver's & Planck's Tavern & more. 12 minutes from Cape Cod Inflatable Park. Large, fully enclosed pool is just steps away. new: - kitchen with new range, DW, fridge, Keurig/drip coffee maker, cookware. New bathroom w/walk in shower, washer & dryer. Smart TV, Roku, internet, fireplace, AC in summer.

May 10 – 17

ﺩ.ﺇ576 per night

Guest favorite

Condo in Truro

4.82 out of 5 average rating, 51 reviews

Designer Studio Condo with peeks of Cape Cod Bay.

MEMORIAL DAY WEEKEND SPECIAL, 15% Discount! See 'my property'. Beautiful, unique designer condo. Photos show what makes my place stand out from others. Please view and read captions ! 10 minute walk to Bay beach, 10 minute drive to Provincetown. Peeks of blue bay from private, spacious deck. Near Atlantic beaches, Truro vineyards, historic lighthouse & Wellfleet. Quiet in unit, 2nd floor, no one above. Guests 21+ welcome, 3 night minimum 5/20 to 6/27 check ins, 4 nights 6/28 to 9/1 check ins

Aug 29 – Sep 5

ﺩ.ﺇ716 per night

Guest favorite

Apartment in Hyannis

4.89 out of 5 average rating, 102 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, and kettle. This studio has air conditioning.

Jul 12 – 19

ﺩ.ﺇ1,071 per night

Guest favorite

Home in Eastham

5.0 out of 5 average rating, 9 reviews

Modern Beach House w/ Heated Pool & Game Room!

Relax at this peaceful newly renovated home with every amenity! Come to your very own private resort on Cape Cod, located on a quiet cul-de-sac in Eastham with tons to offer. Central A/C, heated pool, projector theater, game room, fire pit, outdoor grill w/ dining area and much more! Gimlet Getaway, as we have coined this oasis, is the perfect mix of relaxing Cape Cod and every ounce of a good time w/ all modern comforts and amenities. Message me for details! POOL IS SEASONAL (May-Oct).

Dec 16 – 23

ﺩ.ﺇ2,940 per night

Superhost

Condo in West Dennis, Dennis

4.79 out of 5 average rating, 29 reviews

Hidden Hideaway

Welcome to Mid Cape Cod. Location, Location, Location. Wake up in the morning and have coffee on your private patio. The view overlooks the well manicured back yard bordered by tress and bunnies running around. After coffee, walk down main street for breakfast and more coffee at 3 Fins. Now that you are hyped, walk across the street and rent a Kayak or SUP for the day. Paddle out the Bass river down to the Nantucket sound. Have lunch next door at Sundancers.

Apr 3 – 10

ﺩ.ﺇ410 per night