Holiday rentals with a pool in Wellfleet

4.9 out of 5 average rating, 31 reviews

A charming cottage features shingle siding and a well-maintained exterior. A large deck with a grill is visible at the front. Surrounding greenery and a stone pathway lead to the entrance, which is framed by large windows allowing natural light into the interior.

Cottage in North Truro

Beachside cottage with pool in Provincetown

Relax with family or friends at this cottage at Beach Point Club. Enjoy a BBQ on the large deck or walk to the beach on the boardwalk, which is steps away from the cottage. Take in the water view from the side of the deck, hop on the shuttle to downtown Provincetown, or relax by the pool. Bedrooms contain queen beds. There are mini splits in the living room and bedrooms. Open-concept kitchen contains cooking basics and a Keurig. Linens provided. Pool open mid June to Sept. No smoking & no pets.

An open living area features large glass doors that provide views of the golf course. A comfortable seating arrangement includes a recliner and a sectional sofa. A spiral staircase leads to the loft above, and a mounted television is positioned above a modern fireplace.

5 out of 5 average rating, 88 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.

4.95 out of 5 average rating, 128 reviews

The expansive pool, surrounded by a landscaped yard, features a vibrant blue surface reflecting the clear sky. Comfortable lounge chairs are positioned alongside, inviting relaxation. A floating inflatable adds a playful touch to the tranquil setting.

Home in Cotuit

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!

A welcoming entryway is observed, featuring a rustic 'WELCOME' sign on the wall. Light wood flooring extends into a cozy living and dining space, illuminated by natural light. A dining table is visible in the background, surrounded by comfortable chairs.

4.97 out of 5 average rating, 197 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!

4.98 out of 5 average rating, 105 reviews

A cozy living area is furnished with a comfortable sofa adorned with decorative pillows. A dining table with seating for four is visible, alongside a well-equipped kitchen in the background. Natural light enters through the windows, highlighting the warm wood floors.

Flat in Wellfleet

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.

4.81 out of 5 average rating, 70 reviews

A light-filled living area is presented, featuring a cozy sofa and modern seating around a circular table. A well-equipped kitchen is visible in the background, complemented by large windows that open to the private deck with greenery.

Apartment in North Truro

Designer Studio Condo with peeks of Cape Cod Bay.

Beautiful, unique designer condo with custom built ins. 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 very large private deck. Near Atlantic beaches, Truro vineyards, historic lighthouse & Wellfleet. Quiet in unit, 2nd floor, no one above. Guests 21+ welcome. 4 night minimum. 10% discount for 7 nights, 15% discount for 10 nights. Please read more details in 'The Space'

A communal pool area features a clear blue pool surrounded by concrete decking. Lounge chairs are arranged neatly on the sides, with greenery visible in the background. A wooden fence encloses the area, providing a private atmosphere.

4.91 out of 5 average rating, 115 reviews

The Sea Salt Studio - Steps to the Beach!

Gorgeous studio (Unit #1) only 175 yards from white sand Glendon Road beach. Soak up the sun at the beach, relax by the pool or enjoy a relaxing cocktail on your own private patio. This studio is equipped with a fridge, microwave and gas stove as well as a fully stocked kitchenette and cable/Roku TV. A futon couch offers extra sleeping space, if needed. Outside, enjoy a natural gas grill. Walk or bike to multiple restaurants, ice cream shops and all the amenities Dennis Port has to offer.

5 out of 5 average rating, 13 reviews

Home in Chatham

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.

4.93 out of 5 average rating, 100 reviews

The exterior of the cottage features a well-maintained lawn with lush green trees in the background. A wooden deck extends from the house, along with patio chairs overlooking a tranquil pond surrounded by vibrant flowers and plants.

Cottage in Centerville

The Holly Cottage

Welcome to Centerville, enjoy this fully equipped 1 bedroom 1 bath home with an easy walk or ride to just about everything. Enjoy the nearby ocean and beaches, or take a ride downtown to Main Street for dining and entertainment. Only a short distance to the ferries for a day trip to the islands and you can be back in time to catch a concert at the Melody Tent. Enjoy your days by the pool and your evenings grilling out on the large deck or chatting with the koi fish.

4.9 out of 5 average rating, 144 reviews

A private deck is showcased with outdoor furniture, including a round table and chairs. A colorful striped umbrella provides shade, while surrounding greenery and flowers add a natural touch. The deck is well-lit by sunlight, creating a warm and inviting space.

Flat in Hyannis Port

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. Keurig, and kettle.

Apartment in Provincetown

A scenic view showcasing the bay with gently rippling waters and distant land on the horizon. The foreground features coastal vegetation, including pines and shrubs, along a wooden pathway leading toward the beach. Nearby, a stop sign indicates road access.

4.97 out of 5 average rating, 240 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.

4.88 out of 5 average rating, 34 reviews

A light-filled living area features a beige sofa and a matching loveseat, accented by navy and white decorative pillows. A round wooden coffee table sits in the center, surrounded by a patterned area rug. Sliding glass doors provide access to the outdoor space.

Townhouse in Brewster

Ocean Edge Townhouse/Pool Access

End unit townhouse located in heart of OE Villages with private patio, A/C & W/D. There’s no better way to experience all that Brewster has to offer than taking your family to stay at the Ocean Edge Resort. Just minutes off the property you will find yourself at the beach, on the golf course, or at one of the many excellent local restaurants. Unit has pool & fitness access for additional fees.

Popular amenities for Wellfleet rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.76 out of 5 average rating, 33 reviews

An inviting outdoor space is depicted, featuring a spacious in-ground pool surrounded by lounge chairs. String lights are strung across the pool area, illuminating the backyard. A pool house and umbrellas provide additional amenities, while the home's facade is visible in the background.

Home in Barnstable

Heated Pool Oasis | 5 Min to Cape Cod Beaches!

4.97 out of 5 average rating, 65 reviews

A saltwater pool is set within a stone patio area, surrounded by lush greenery. Lounge chairs and a shaded table with a red umbrella offer comfortable seating options. The serene view of Morey Pond is visible beyond the pool, framed by trees under a clear blue sky.

Home in Plymouth

Our families slice of heaven

4.8 out of 5 average rating, 30 reviews

The exterior showcases a contemporary home with a blend of stone and siding elements. Solar panels are visible on the roof, and a circular driveway leads to a welcoming entrance with double doors. Surrounding greenery enhances the property’s serene setting.

Home in Sagamore

Sagamore Manor | Pool | Hot Tub | 5min to Beach!

4.97 out of 5 average rating, 29 reviews

An outdoor pool area showcases a heated inground pool with clear water, surrounded by a wooden deck. Sun loungers are placed nearby, and patio umbrellas provide shade. Lush greenery and trees line the background, offering a serene environment. A beach ball floats in the water.

Home in New Seabury

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

4.88 out of 5 average rating, 25 reviews

An aerial view of a spacious backyard features a heated pool surrounded by a grey stone patio. Lounge chairs and umbrellas are positioned around the pool. The house showcases multiple large windows and a deck, with green grass and trees creating a private setting.

Home in Plymouth

Mansion with Heated Pool Near Ocean

4.74 out of 5 average rating, 69 reviews

Home in Plymouth

Private Plymouth Retreat w/ Pool, Game Room & Fire

4.95 out of 5 average rating, 20 reviews

A bright bedroom features a spacious bed with striped bedding and decorative pillows. A cozy throw blanket is placed at the foot of the bed. Natural light filters through the two windows, and a floor lamp adds additional lighting. A framed art piece is mounted on the wall.

Home in East Sandwich

Coastal Retreat in Sandwich -Pool Access, Dogs OK!

4.92 out of 5 average rating, 49 reviews

A spacious outdoor area is highlighted by a seasonal heated pool surrounded by a wooden deck. Multiple blue lounge chairs are arranged around the pool, and a fire pit table is situated at the center. A large checkers board and garden beds add to the inviting atmosphere.

Home in Yarmouth Port

Winslow Acres [heated] Pool Escape; pool May-Oct

Apartment rentals with a pool

A spacious sleeping area features a large bed with neutral bedding and colorful accent pillows. A TV is mounted on the wall. Natural light filters through a sliding glass door, which opens to an outdoor area with a small table and chairs.

4.82 out of 5 average rating, 74 reviews

Cozy Studio Just Steps Away From the Beach!

4.93 out of 5 average rating, 44 reviews

A light-filled living area features a cozy sofa layered with a soft throw, accompanied by a stylish coffee table. The calming wall art depicts ocean waves, while lamps provide additional lighting. A door leads outside, and a chair adds a pop of color.

Apartment in West Dennis

1BR 2nd Floor Condo with pool

The spacious living area features a queen-sized bed and a comfortable sofa. A dining table with two chairs sits near the window, allowing natural light to brighten the room. Simple decor includes star-shaped wall accents, enhancing the relaxed coastal ambiance.

4.84 out of 5 average rating, 87 reviews

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

4.85 out of 5 average rating, 55 reviews

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

The living area features a light-colored sofa paired with matching armchairs. A small table holds fresh flowers. Soft lighting from lamps creates a comfortable environment. Large sliding doors provide natural light and open to an outdoor patio with a dining set.

4.96 out of 5 average rating, 95 reviews

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

The studio features a spacious bed adorned with colorful decorative pillows. A seating area with a small table and golden chairs is visible. Light pours in through sheer curtains, complemented by three framed art pieces on the wall, adding character to the bright space.

4.88 out of 5 average rating, 75 reviews

Stylish & Modern Studio Condo - Steps to the Beach

Apartment in Provincetown

The open living space features large windows providing direct views of Cape Cod Bay. A light-colored sectional sofa is positioned to maximize views, while a ceiling fan offers air circulation. The room's modern decor is complemented by natural light streaming through the windows.

4.85 out of 5 average rating, 39 reviews

Spectacular Waterfront Condo

Apartment in Provincetown

A modern living area features a vibrant orange sectional sofa complemented by light walls and hardwood flooring. A glass coffee table sits centrally, while a small dining area with white chairs is visible. Artwork adorns the walls, contributing to a welcoming ambiance.

4.94 out of 5 average rating, 48 reviews

Newly Updated Condo w/ Pool - Steps to Boatslip!

Other holiday rentals with a pool

4.92 out of 5 average rating, 25 reviews

A welcoming entrance is framed by light-colored siding, with a wooden deck leading to a glass-paneled door. The bright sun is positioned directly above, creating a halo effect. Lush green shrubs and a gravel pathway add to the inviting exterior.

Holiday home in Truro

Spacious, newly updated condo

An elevated deck overlooks a serene river view, featuring several white Adirondack chairs and a red picnic table. The warm wooden floor enhances the inviting outdoor space, complemented by lush greenery in the background under a clear blue sky.

Flat in South Yarmouth

4.8 out of 5 average rating, 5 reviews

Studio w/ Kitchenette & Patio in Cape Cod

4.87 out of 5 average rating, 15 reviews

The lighthouse features a round white structure topped with a lantern room. A spacious deck wraps around the building, accompanied by a well-maintained lawn and a decorative pumpkin. American flags are displayed, and the surrounding area includes additional nearby structures and views of the water.

Tower in West Dennis

Jolly Captain Lighthouse

A dining area features a round white table surrounded by four sleek chairs. A small vase with flowers sits at the center of the table. Large windows allow natural light to fill the space, offering a view of the trees outside.

4.8 out of 5 average rating, 49 reviews

Golf Course Views and Pools

5 out of 5 average rating, 14 reviews

An open floor plan features a modern kitchen equipped with high-end appliances, a comfortable gray sofa facing a wall-mounted TV, and a dining area. A striking skylight allows natural light to fill the space, while a stylish area rug adds warmth. A pull-out staircase leads to the lofted bedroom.

Tiny home in North Truro

Modern East End Loft - Private Beach & Pool Access

5 out of 5 average rating, 19 reviews

A heated saltwater pool is surrounded by four lounge chairs and two umbrellas, offering shaded relaxation. A wooden poolside structure with seating is visible in the background, complemented by a natural setting with trees and a fenced perimeter.

Home in North Eastham

Cape Cod Oasis: Pool, Game Room, Bike Path!

4.94 out of 5 average rating, 31 reviews

The exterior of the cottage is showcased with a textured shingle facade and a white door framed by two green shutters. Surrounding the entrance, vibrant blue hydrangeas bloom, complemented by a neatly trimmed evergreen shrub. A gravel pathway leads to the door, enhancing the inviting appearance.

Cottage in East Sandwich

Charming E. Sandwich Cottage Near Beaches, Dogs OK