
Vacation rentals with a pool in Wellfleet
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Wellfleet
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Stunning Cape Home - Inground Pool, 5 Min To Beach
Stunning in-ground pool HEATED in May, June, Sept, Oct only. 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!

XL Estate: 2 Homes-Pool-Tennis-Game Barn - 20 ppl
Our Cape Cod Estate is truly one of a kind. This 2+ acre retreat boasts an extraordinary design built in the 1800s and updated with modern luxuries. Enjoy room for up to 20 guests with two homes, a separate bar and game barn and tons of amenities! Centrally located within 5 minutes of three public beaches, shops, dining & golf! The perfect getaway for family reunions, group vacations, wedding parties, corporate retreats, and more! SUMMER MONTHS: - Weekly bookings only - Saturday to Saturday

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

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!

Cape Cod Heated Pool Putt-Putt Golf Speak Easy Gam
Nestled in a serene neighborhood, our spacious and beautifully appointed pool house offers the perfect balance of comfort, style, and convenience. The centerpiece is the private heated pool, perfect for taking refreshing dips or lounging. Enjoy alfresco dining with the gas grill and outdoor seating area, ideal for family barbecues or sunset cocktails. As night falls, gather around the firepit to share stories and enjoy the starry sky—your own private escape just steps away from the front door.

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.

Heated Pool, Game Room, Projector Room, Private
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-Sept)

Luxury Home w/ Salt Water Pool Overlooking Ocean
Welcome to your dream Cape Cod getaway! Our brand-new, fully renovated 4-bedroom, 5-bath luxury home offers breathtaking views of Buck’s Creek and Nantucket Sound, creating the perfect backdrop for your vacation. Inside, you'll find a stunning cathedral-ceiling living room designed for relaxation and gathering. The chef’s kitchen features a massive 15-foot eat-in island, perfect for family breakfasts or evening cocktails. Each of the spacious bedrooms offers comfort and privacy.

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).

Family Fun- Games, Pool & HotTub, Dogs ok! Slps 10
Welcome to Sesuit Harbor Hideaway – your perfect Cape Cod getaway! This spacious 4-bedroom, 3-bathroom home offers a relaxing escape, complete with all the amenities you need for an unforgettable vacation. Nestled in a quiet, charming neighborhood, it’s ideal for families, friends, or groups looking to enjoy the best of the Cape. 6min to Cold Storage beach 5min to Sesuit Harbor Café 3min to Dennis Pines Golf Course 3min to Scargo Tower 10 minutes to Mayflower Beach

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.

Hot Tub, Game Room, near mayflower beach
Your family will be close to everything when you stay at this centrally-located place. 3 miles to Mayflower beach and Coorporation beach. 10 minutes to Harwich port and Chatham. Great location. Private new hot tub. 4 bedrooms. Sleeps up to 12. Game room fire pit bbq and so much more. Create your cape memories year after year at this perfect cape cod gem. No parties.
Popular amenities for Wellfleet rentals with a pool
House rentals with a pool

Renovated Cape Oasis W/ New Pool and Game Room!

Beautiful Mashpee Home with Pool

"Cape Escape" luxury home w/pool & beach access.

Beachside Retreat pool&spa bball court

Exclusive New Seabury Home w/ Heated Pool ⛳️🏖🦞☀️🐠

49 Clover Lane, 3 beds, 3.5 baths, pool & firepit

ShoestringBayHouse, waterfront & pool in Cotuit

Cape Cod Lakefront Home
Condo rentals with a pool

Cozy Studio Just Steps Away From the Beach!

Ocean Edge: 2 bed/2 bath - Pools & Resort Access

Unit #6 - 2nd Floor- Efficiency Studio, with A/C

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

Hidden Hideaway

Spectacular Waterfront Condo

Bright Beach Condo • Walk to Sand & Shops

Newly Updated Condo w/ Pool - Steps to Boatslip!
Other vacation rentals with a pool

Oceanfront location with amenities

Waterfront Home w/ Dock, Heated Pool, Kayaks & A/C

Spacious, newly updated condo

Fenced Pool, Fire pit, Outside dining, Coffee bar

Pet Friendly King Suite in a great location

Hyannis Port Coastal Escape – Pool & Walk to Beach

Cape Home w/Oceanview, Roof Deck Pool & Hot Tub

Modern East End Loft - Private Beach & Pool Access
Quick stats about vacation rentals with a pool in Wellfleet

Total vacation rentals
Explore 20 vacation rentals in Wellfleet

Nightly prices starting at
Wellfleet vacation rentals start at G$14,645 GYD per night before taxes and fees

Verified guest reviews
Over 770 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space & kid-friendly amenities

Wi-Fi availability
20 of Wellfleet vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Wellfleet rentals

4.7 Average rating
Wellfleet stays receive an average rating of 4.7 out of 5 from guests
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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
- Pinehills Golf Club
- Chapin Memorial Beach
- Inman Road Beach
- Lighthouse Beach
- Minot Beach
- Nauset Beach
- Town Neck Beach
- Ellis Landing Beach
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- Peggotty Beach
- Nickerson State Park
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