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Vacation rentals with a pool in Osterville, Barnstable

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Top-rated rentals with a pool in Osterville, Barnstable

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

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Home in Barnstable

4.88 out of 5 average rating, 34 reviews

Paradise home in centerville

Have you always dreamed of a getaway on Cape Cod at what feels like your very own private resort? Here it is! All amenities of a resort made privately available to you, all in one place. Take a swim in this magnificent pool, workout at the gym, relax in the jacuzzi, unite all around the fire or the pool table, gather a team to play basketball or soccer, let the kids play in the playground or the arcade while you cook in your outdoor kitchen or bathe in the sun by the pool. Live the way you dream

Home in Hyannis Port

5 out of 5 average rating, 11 reviews

Home in Hyannis Port

Welcome to "The Sand Box” in Hyannis Port, our Cape Cod Rental. We can’t wait to answer all your questions about our property! Our home is 4 bedroom, 2 full bath that was fully renovated in October of 2021. It’s walking distance to two beaches and central to many more across Barnstable. Lush outdoor entertainment area with an in-ground pool and patio with an outdoor gas grill. 5 minute drive from downtown Hyannis. It’s a fantastic getaway for 4 couples or for a whole family. Cert# C0457270200

Home in Cotuit

4.95 out of 5 average rating, 113 reviews

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!

Condo in Brewster

4.97 out of 5 average rating, 177 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!

Home in Sandwich

4.99 out of 5 average rating, 80 reviews

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

Welcome to the Cape Escape! Enjoy views of Spectacle Pond from the 70 ft. deck of this recently renovated 5 bed/3 bath spacious home meeting all your needs! Relax by the in-ground pool in the private enclosed yard. Enjoy nights around the fire-pit. Directly across the driveway you can enjoy kayaking, sunbathing & swimming at the neighborhood beach. Within 6 miles of the home you will find the historic Sandwich boardwalk, Ocean beaches, Cape Cod Canal and more! Perfect for family gatherings!

Home in Cotuit

4.94 out of 5 average rating, 18 reviews

ShoestringBayHouse, waterfront & pool in Cotuit

Welcome to ShoestringBayHouse, waterfront on Popponesset Bay. All rooms and decks overlook the beach & bay. Included: Bikes, Kayaks, and beach pass. Pool is serviced: Memorial Day to Labor Day Our bay front home with 4 BR/ 4.5 baths is priced for six (6) guests but our home will accommodate up to eight (8) guests at additional cost. (please inquire about group size) Extra guests (age 12+) at $60/night. (no charge for young children/ toddlers) **displayed rates reflect six occupants.

Guest suite in Centerville

4.99 out of 5 average rating, 71 reviews

Cape Cod Hideaway

Enjoy a bit of Cape Cod in a neighborhood of lush green trees , flower gardens, and a walking trail. Less than 1 mile from Centerville's shops and restaurants. Only 2 miles from Craigville Beach and its beachside walk up shanty’s for fresh seafood / burgers. Main street Hyannis is the "Hub" of the Cape and a quick 10-minute drive. Explore the many beaches and local fare by day and the lively clubs at night. Ocean docks, marinas, and ferries to the islands are a 10–15-minute drive.

Rental unit in Barnstable

4.93 out of 5 average rating, 29 reviews

Studio Apartment

Private Studio apartment on lower level with deck overlooking Pond. Queen bed, single sleeper sofa and small sleeping loft. Very comfortable for 2 people but could sleep up to 4. Kitchenette with dinnerware and cookware. Coffee maker, full size fridge, microwave, toaster oven, outside gas grill. Private bath with shower. TV, WiFi, A/C. Pond access, SUP, kayaks available. Pool and hot tub at Main House. Sunrise views. Golf courses, shopping, restaurants, and beaches nearby.

Condo in New Seabury

4.98 out of 5 average rating, 128 reviews

Sleep 6 @ New Seabury w/ Pool Access, All Seasons!

Welcome to our beautiful Cape Condo located in The Mews at New Seabury Country Club in Mashpee, MA. Our unit provides access to a private condo association pool a 3 min walk from the unit. Also, we have: -5 min bike/car ride to beach -Central air, wifi, cable, gas grill -Located on Championship Golf Course -Beach chairs, beach towels/toys -New Seabury Village restaurants, mini-golf, bowling, museums -20 min drive to Hy-Line Ferry to Nantucket/Martha's Vineyard

Townhouse in Brewster

4.86 out of 5 average rating, 103 reviews

Ocean Edge Cape House with Beach, Pool, and AC

Classic Cape Cod Cottage with air conditioning in the heart of The Cape with access to a private beach, swimming pool, and tennis courts. Walk to the store, restaurants and easy access to the Cape Cod Rail Trail. Walk, bike or drive to Nickerson State Park for hiking trails, fresh water swimming, paddle boarding, and fishing. This is a perfect setting for families with plenty of green space and a gated community. The house has a grill and 2 balconies to enjoy.

Rental unit in North Falmouth

4.83 out of 5 average rating, 138 reviews

Quaint North Falmouth near Old Silver Beach

Located in the Quaint village of North Falmouth, yet close to beaches, this one-bedroom Apartment is a great place to relax. It has a tiled walk-in shower and heated floor in the bathroom. The kitchen includes a microwave, toaster oven, cook top stove, and a Keurig coffee maker. The pool is not heated and is open seasonally (July 1 - Labor Day) Very private location. Close to Old Silver Beach!

Rental unit in Hyannis Port

4.88 out of 5 average rating, 88 reviews

Cute Cottage Near Beach & Main Street 3BR/3BA (15)

Stay at a charming 3-Bedroom cottage in a beautiful setting within walking distance to Cape Cod's warm sandy beaches and Main Street Hyannis. Captain Gosnold Village is ideally located within a short walk from three of the Cape's best beaches and nestled between picturesque Hyannis Port and the vibrant atmosphere of Hyannis Harbor with its island ferries, sightseeing and fishing charters.

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Popular amenities for Osterville, Barnstable rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in Barnstable

4.67 out of 5 average rating, 12 reviews

Stunning Cape Home - Inground Pool, 5 Min To Beach

Home in Dennis

4.63 out of 5 average rating, 30 reviews

House on Cape Cod with pool close to beach

Home in East Falmouth

5 out of 5 average rating, 8 reviews

Sunny Loft - Seasonal Pool & Beach access

Home in Brewster

4.97 out of 5 average rating, 31 reviews

Modern Cape, Private Salt Water Pool, Beaches-Golf

Home in Plymouth

4.75 out of 5 average rating, 55 reviews

The Poppy: Tranquil Family Home With Arcade

Home in Forestdale

4.64 out of 5 average rating, 11 reviews

New Cape Escape for 10 People With Heated Pool

Home in Mashpee

4.81 out of 5 average rating, 54 reviews

Sunny Cape w/Private Pool, Steps to Private Lake

Home in East Falmouth

4.94 out of 5 average rating, 31 reviews

Dog Friendly Cape Oasis | Pool+Beach |Tennis Court

Condo rentals with a pool

Condo in Dennis Port

4.78 out of 5 average rating, 58 reviews

Cozy Studio Just Steps Away From the Beach!

Condo in West Dennis

4.89 out of 5 average rating, 28 reviews

1BR 2nd Floor Condo with pool

Condo in Brewster

4.98 out of 5 average rating, 56 reviews

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

Condo in Dennis Port

4.84 out of 5 average rating, 58 reviews

Stylish & Modern Studio Condo - Steps to the Beach

Condo in West Dennis

4.84 out of 5 average rating, 51 reviews

Hidden Hideaway

Condo in Falmouth

5 out of 5 average rating, 4 reviews

InnSeason Resorts Captains Quarter's

Condo in Hyannis Port

4.82 out of 5 average rating, 17 reviews

Beachfront Complex in Hyannis

Condo in Brewster

5 out of 5 average rating, 71 reviews

Ocean Edge Resort/Pool access/2bedroom-2bath Condo

Quick stats about vacation rentals with a pool in Osterville, Barnstable

Total rentals
20 properties
Nightly prices starting at
$160 before taxes and fees
Total number of reviews
120 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

Destinations to explore