Holiday rentals with a pool in Wellfleet

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Top-rated rentals with a pool in Wellfleet

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

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Guest favourite

Apartment in Brewster

5 out of 5 average rating, 72 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.

Guest favourite

Apartment in Brewster

4.97 out of 5 average rating, 180 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!

Top guest favourite

Flat in Wellfleet

4.97 out of 5 average rating, 75 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

Apartment in Truro

4.81 out of 5 average rating, 64 reviews

Designer Studio Condo with peeks of Cape Cod Bay.

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, 4 night minimum 5/22 to 6/29 check ins; 5 nights 6/30 to 9/1 check ins; back to 4 nights for 9/2 to 10/31 check ins

Top guest favourite

Home in Oak Bluffs

4.93 out of 5 average rating, 198 reviews

Spectacular beach & pool combo; beautiful sunsets!

Close to airport, you’ll love backyard beach, water view, pool/grass yard, ambiance and outdoors space. Beach & Pool (POOL HEAT STARTS SUMMER, ENDS 9/1) is a hard to find combination!! Location is private, yet it's close to the 3 largest towns on Martha's Vineyard. Great for couples, families (with kids), and big groups. Enjoy dinner with the indoor/outdoor Sonos music system during a beautiful sunset! NOTE; Rate increase in high season, pool/spa is a combined unit & ONLY heated in summer!

Guest favourite

Flat in Hyannis Port

4.88 out of 5 average rating, 125 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.

Guest favourite

Apartment in Brewster

4.92 out of 5 average rating, 50 reviews

Stylish Ocean Edge Condo #TheCouplesNest

Experience Cape Cod from our stylish 2nd floor condo in Fletcher Village at Ocean Edge, Brewster. Centrally located, it offers easy access to beaches, the Rail Trail, and local dining. Enjoy amenities like pools, tennis, and golf. The modern condo features a fully equipped kitchen and a balcony, perfect for relaxation or adventure throughout the year. Whether you're biking on scenic trails or relaxing by the pool, our condo provides the ideal setting for a memorable Cape Cod experience.

Superhost

Home in Plymouth

4.9 out of 5 average rating, 120 reviews

Seaview Summit | Ocean Views, Indoor Pool, Beach

Welcome to Seaview Summit House, where you can enjoy breathtaking panoramic ocean views, take a dip in our heated swimming pool, and take a short walk to the beach. Our spacious and beautifully decorated home features a large living area with comfortable seating, a fully equipped kitchen with all the essentials, and a dining area that seats everyone. You'll have plenty of room to spread out and enjoy your time together, whether you're lounging inside or soaking up the sun outside.

Guest favourite

Home in Dennis Port

4.92 out of 5 average rating, 50 reviews

Walk to the beach or sit poolside! Updated studio!

Adorable condo in the heart of vacationland in Dennis Port! This studio unit is full of natural light and comfortable for two people! The floor plan offers a living area with a queen sized bed and a pull out full sofa. Step out the sliders onto a deck with outdoor seating. There is a shared association pool open mid June- Aug. All this and right in the middle of the summer fun of Dennis Port and all its activities. The beach is under 1/4 mile away in walking distance.

Guest favourite

Home in North Eastham

5 out of 5 average rating, 14 reviews

Eastham is Cape Cod’s best kept secret!

Enjoy the heated salt water pool (open Memorial day to Columbus day) bike trail outside back gate, pizza oven, outdoor seating area, deck with dining area, 3 season room as well as two first floor seating areas and a full finished basement play area. Enjoy all that Cape Cod has to offer with beaches, hiking, and restaurants all within minutes of our home. Come home to the outdoor grill and pizza oven and enjoy the outdoors as well as the luxury of the indoor spaces.

Top guest favourite

Campervan/Motorhome in Wellfleet

5 out of 5 average rating, 29 reviews

Seasonal 27’ Retro Glamping Steps From Bike Trail

A SECLUDED WELLFLEET LOCATION, STEPS FROM BIKE PATH WITH DELIGHTFUL AMENITIES. This 27’ Camper with upgrades, and shared HEATED 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 Families looking to enjoy beautiful Wellfleet. Heated Pool* is great option when weather is cool, cloudy.

Guest favourite

Apartment in Provincetown

4.97 out of 5 average rating, 216 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.