Vacation rentals with a pool in Orleans

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Popular amenities for Orleans rentals with a pool

House rentals with a pool

Top guest favorite
The outdoor pool area features a clear blue pool surrounded by a concrete patio. Sun loungers and white Adirondack chairs are positioned nearby. A shaded cabana provides relief from the sun, complemented by lush greenery in the background, enhancing the serene atmosphere.
Home in North Eastham
5 out of 5 average rating, 18 reviews

Heated Pool, Game Room, Projector Room, Private

AstridRating, 5 stars4 weeks ago
If i could give more than 5 starts I would! Stephanie and her place were exceptional! We had a bachelorette party and we stayed at Stephanie’s place. Stephanie went out of her way to help me decorate for the bachelorette party. She was very responsive and so helpful throughout my planning. The house is amazing! Looks exactly like the photos and it is clean and in a safe and quiet neighborhood. There 11 of us and we fit comfortably! Thank you so much for hosting us Stephanie and to anyone booking I would 100% recommend staying here!
Top guest favorite
An expansive outdoor area features a rectangular saltwater pool surrounded by a concrete deck. The historic house presents a mix of shingle-style architecture and modern updates. Lush greenery and trees frame the property, with clouds and blue skies providing a scenic backdrop.
Home in East Sandwich
5 out of 5 average rating, 31 reviews

XL Estate: 2 Homes-Pool-Tennis-Game Barn - 20 ppl

BobRating, 5 stars1 month ago
Joshua's place was the PERFECT place for our dad's 70th birthday! The 9 kids had an amazing time between the pool and game barn there was constant entertainment for all ages! If you have a big family/group this is the spot!
Superhost
A serene backyard setting features a private pool surrounded by a spacious patio. A sunbathing chair and a BBQ grill are positioned nearby, with a house showcasing large windows that invite natural light. Lush greenery frames the area, providing a sense of tranquility.
Home in Dennis
4.63 out of 5 average rating, 30 reviews

House on Cape Cod with pool close to beach

KeelyRating, 5 stars10 months ago
Alena's place had everything we needed for a lovely week on the Cape. Great pool and location between Mayflower and Dennis Village. My daughter loved the home's bright airy playroom and it kept us sane and entertained on a couple of rainy days. Would definitely visit again!
Top guest favorite
Home in Sandwich
4.99 out of 5 average rating, 82 reviews

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

JanelleRating, 5 stars4 weeks ago
We have stayed in multiple houses / penthouses throughout the U.S. , however, this home surpassed them all. Jennifer was amazing from the beginning of the booking with answering my questions and went above and beyond to make this special occasion memorable. The house is well equipped! The sounds of birds chirping in the morning , the breeze, and the view of the pond when drinking coffee was so serene. The space in the house was more than I expected with everyone having lots of space to enjoy all the designated areas for playing board games, Video game room( so cool) , reading , watching tv - there was a room for everyone’s enjoyment from our 12 year old, 17, 25, to my 78 year old parents. The well thought out toiletries in every bathroom, spa slippers and robes in each bedroom, ear plugs located by the bedside, laundry room that has labeled racks of beach items and games , kitchen with all its wonderful amenities- I can do on and on. We WILL be back !
Guest favorite
The spacious outdoor area features a heated saltwater pool surrounded by paver stones. Lounge chairs are positioned around the pool, accompanied by blue umbrellas. A nearby cabana is visible, along with vibrant landscaping, providing a relaxing atmosphere for guests.
Home in Popponesset
5 out of 5 average rating, 13 reviews

18 Menemsha Rd., Popponesset, Pool, 3-Beds, 4 bath

CarolRating, 5 stars1 month ago
We loved are family stay at Paul & Katie’s home for Easter Week. It is a dream home . The neighborhood was beautiful and walkable, with a peaceful path to a private beach. We enjoyed the shops and restaurants in Mashpee Commons about an 8 minute drive away.
Guest favorite
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
5 out of 5 average rating, 20 reviews

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

AriannaRating, 5 stars2 weeks ago
We had a wonderful stay here in New Seabury! The house is beautiful, spacious and just as described. The heated pool was an added bonus! Michael provided prompt and clear communication when needed. I would absolutely stay here again!
Top guest favorite
A spacious backyard features a large swimming pool surrounded by a well-maintained lawn. Comfortable lounge chairs are arranged along the pool's edge, while a charming shed is visible in the background. Lush greenery borders the area, enhancing the outdoor setting.
Home in Buzzards Bay
5 out of 5 average rating, 27 reviews

Cape House with Pool by Canal

SamanthaRating, 5 stars9 months ago
This home was great for our family. The pool and backyard are beautiful, and the house was clean and welcoming. There are a lot of activities in the area. I would stay here again!
Superhost
The exterior of the home is presented with natural wood siding, complemented by green shutters. Solar panels are mounted on the roof. A welcoming front porch leads to the main entrance, while a garage is visible to the left amidst well-maintained landscaping.
Home in Harwich
4.81 out of 5 average rating, 16 reviews

4 BD slice of Harwich Heaven

ValerieRating, 5 stars6 days ago
My friends and I always wanted to visit Cape Cod and Chris’ home felt just like that place to stay in. He was very responsive and helped me a lot with recommendations! If I were to come back, I would stay here again. The house was very spacious, can’t complain there!

Condo rentals with a pool

Guest favorite
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.
Condo in Dennis Port
4.78 out of 5 average rating, 58 reviews

Cozy Studio Just Steps Away From the Beach!

NupurRating, 5 stars9 months ago
Perfect little studio for two people! Great location - close to beaches and restaurants and there’s even a pool! Michael was super responsive and the place was exactly like the pictures!
Guest favorite
A clean outdoor pool is framed by a spacious concrete deck with lounge chairs positioned nearby. Lush greenery and landscaped areas are visible around the pool, contributing to a serene environment. The sky above is clear, enhancing the bright atmosphere of the setting.
Condo in West Dennis
4.9 out of 5 average rating, 30 reviews

1BR 2nd Floor Condo with pool

DougRating, 5 stars6 days ago
The unit was secure and in a nice area. Close to shopping, sightseeing, and beaches. The unit was bright and cheery and clean. Keith is a good host.
Guest favorite
A charming, single-story building is visible from the road, featuring a gray exterior and a white picket fence that encloses a well-kept yard. Leafy trees provide shade, and clear blue skies are overhead, creating a welcoming ambiance for guests.
Condo in Dennis Port
4.84 out of 5 average rating, 76 reviews

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

ChrisRating, 5 stars9 months ago
Wonderful beach location. We enjoyed the local walkable beaches and restaurants. Close to anywhere in the cape , we had a great trip.
Superhost
A clear blue pool is surrounded by lounge chairs, offering a refreshing spot for relaxation. The two-story building in the background features balconies with umbrellas and well-maintained landscaping, creating a serene atmosphere for guests.
Condo in West Dennis
4.84 out of 5 average rating, 51 reviews

Hidden Hideaway

JennyRating, 5 stars7 months ago
The location is fabulous and very close to many amenities - coffee, groceries, restaurants and the beach. While it was a small space, it was well laid out, comfortable to be in, very clean and had a respectable kitchen for its small size (which I used). Devon was very proactive and friendly when I asked him about the microwave not working - I had missed that it wasn't plugged in! The condo was very quiet at night even though it is close to a road. I will definitely return to Devon's place should I need to travel there and it is available.
Guest favorite
An unheated communal pool is framed by a tan patio and white fencing. Surrounding the pool, blue lounge chairs and umbrellas provide seating options. The two-story building in the background features a deck with stairs leading to the second floor, bordered by green trees.
Condo in Vineyard Haven
4.9 out of 5 average rating, 73 reviews

Sunny 2bedroom condo w pool, walk to town

ShayRating, 5 stars7 months ago
We had a great time at Leah’s place. She is a terrific communicator, immediate responses. She also reached out to share about local fun events that were happening during our stay. So nice! We would definitely stay there again.
Superhost
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.
Condo in Provincetown
4.9 out of 5 average rating, 30 reviews

Spectacular Waterfront Condo

MeganRating, 5 stars7 months ago
What a special place to have your morning coffee, overlooking the gorgeous ocean views! The place was spotless, exactly as pictured, super clear entry and instructions. So close to all P’town has to offer but just far enough off the main strip for some real peacefulness! Would recommend to anyone! Hosts provide excellent local information and were incredibly communicative. Thank you!
Guest favorite
A comfortable living area features a dark sectional sofa and a light wood coffee table. A large flat-screen TV is mounted on the wall. Bright natural light filters through sliding glass doors, revealing views of the ocean and outdoor deck. Light furnishings enhance the airy feel.
Condo in Provincetown
4.93 out of 5 average rating, 102 reviews

Modern, clean waterviews

LexiRating, 5 stars4 weeks ago
We had a wonderful stay at Garrett’s place. The apartment location can’t be beat, right on the water and walking distance to town but also nice and peaceful. Our family enjoyed the balcony and the comfy living room and kitchen. Would recommend!
Superhost
The entrance of the condominium is shown, featuring a wooden exterior with shingles. A pathway leads to the door, surrounded by neatly trimmed shrubs and grass. Bright sunlight highlights the clear sky and the inviting pathway.
Condo in Falmouth
4.72 out of 5 average rating, 18 reviews

Condo in Falmouth MA

MarkRating, 5 stars1 month ago
The Condo was clean & comfortable. Having two bedrooms with queen beds was perfect for us, and sharing the 1 bathroom worked fine. The price was better than most other options. It was peaceful, and very quiet during our stay (in early May). Having the pool available would be very nice in summer months.

Quick stats about vacation rentals with a pool in Orleans

  • Total rentals

    40 properties

  • Nightly prices starting at

    ﺩ.ﺇ441 before taxes and fees

  • Total number of reviews

    240 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

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