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

“The Hideaway” Private Guest Suite/Pool/Beach Pass
Enjoy a bit of Cape Cod in a friendly and walkable neighborhood of lush green trees , flower gardens, and a walking trail. Less than 1 mile from Centerville's shops and restaurants. Less than 2 miles from Craigville Beach and its beachside walk up shanty’s for lunch. A small beach on Lake Wequaquet is only 2 miles down the road . Main street Hyannis, a walkable downtown with many shops and restaurants is a quick 10-minute drive. Ocean marinas, and ferries to the islands, are a 15 minute drive.

Ocean Edge 2 Bed 2 Bath, Golf & Free Resort Access
Enjoy this 1,000 SF, 2 bed, 2 full new marle tile bathrooms, 2 showers, at Ocean Edge, right in the middle of the golf course. This Airbnb is a full member of the Ocean Edge Resort and allows you access to Ocean Edge golf, and free resort access included up to 6 guests to swimming pools, tennis, gym & pickleball. No one lives here, it is absent of personal items. From the moment you enter, you will know that you have made a great choice and that your time here will be above your expectations.

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!

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.

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.

Renovated Beach Condo - Pool - Hot Tub - Fire Pit!
Your family will be close to everything when you stay at this centrally-located beach condo! Swim in the outdoor pool and hot tub. Enjoy the BBQ or sunsets from your large private deck. Later in the evening, why not stop by the fire pit while your worries drift away. Nothing says summer on Cape Cod like a cozy beach condo in Dennis Port. Head straight to the pool or the beach! With a fully equipped Kitchen with all the necessities, this renovated condo is a beach lover’s paradise.

Carolyn's Bass River Condo
This 600 Sq. Ft. condo is located on Bass River. This vacation unit has two levels. The upper level with balcony overlooking Bass River is a combination living room/dining area with a kitchenette plus a full bathroom. The lower level with access to patio is a bedroom with a Queen pillow top bed and a full bed plus a second full bath. Both levels have through the wall AC/heating units. The 18 unit condo complex has an outside heated pool which is open during summer season.

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.

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.

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.

Bright and Lovely Cottage With Community Pool
Skylights and lots of windows make this contemporary cottage appealing. Just over 1/2 mile to the ocean! Quiet community with pool. One bedroom with queen bed. Loft with twin bed. WIFI, outside shower, locking shed, private deck, fenced yard. Come and relax. Please inquire for any possible flexibility in calendar dates and arrival or check-out times. We will try to help. Incredible bike path nearby!! Sorry - no smoking and no pets.

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 Orleans rentals with a pool
House rentals with a pool

Harwich Haven: Pool & Fire Pit

Harwich House: Private Pool, Game Room & Putt-Putt

5-bedroom Cape with a pool and yard games.

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

Modern Cape, Private Heated Pool, Beach, Golf

4 BD slice of Harwich Heaven

Walk to the beach or sit poolside! Updated studio!

Cape Cod Lakefront Home
Apartment rentals with a pool

Cozy Studio Just Steps Away From the Beach!

1BR 2nd Floor Condo with pool

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

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

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

Stylish & Modern Studio Condo - Steps to the Beach

Mary's Cape Escape

Beachfront Complex in Hyannis
Other holiday rentals with a pool

Studio w/ Kitchenette & Patio in Cape Cod

Pet Friendly King Suite in a great location

Coastal Oasis: Brewster-Cape Cod

Happy Daze are here again! Cute condo by the Bay!

NEW POOL! Sleeps 10+, Perfect for 2 families

A Beautiful Es-Cape

Golf Course Views and Pools

Classic Cape with Heated Pool, AC, King Beds
Quick stats about holiday rentals with a pool in Orleans

Total holiday rentals
Explore 30 holiday rentals in Orleans

Nightly prices starting at
Orleans holiday rentals start at $140 SGD per night before taxes and fees

Verified guest reviews
Over 310 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
30 of Orleans holiday rentals include wifi access

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

4.9 Average rating
Orleans stays are highly rated by guests – averaging 4.9 out of 5!
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- Cape Cod
- Mayflower Beach
- West Dennis Beach
- East Sandwich Beach
- Craigville Beach
- Duxbury Beach
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- Pinehills Golf Club
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