Vacation rentals with a pool in Oak Bluffs

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Top-rated rentals with a pool in Oak Bluffs

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

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Guest favorite

Condo in Mashpee

4.97 out of 5 average rating, 101 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 -2 bicycles available for use -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

Jun 9 – 16

R6,056 ZAR per night

Guest favorite

Villa in Mashpee

5.0 out of 5 average rating, 33 reviews

Heated Indoor Pool & Spa - Golf Course View

CHERRY BLOSSOM RETREAT Cold days, raining days, power outage won't be an issue if you can steal away to this home, with an indoor heated salt water pool and hot tub fully equipped with a backup generator, with a view of the famous 13-Hole Championship Golf Course Cape Cod. Our ultimate luxury home is filled with arcades, air hockey, foosball and other indoor entertainments for guests to enjoy, comfortably sleeps 6-8 and just a few minute drive to all of the amenities New Seabury has to offer.

May 10 – 17

R19,230 ZAR per night

Superhost

Home in Mashpee

5.0 out of 5 average rating, 3 reviews

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

NOTE: Summer calendar is blocked, you must inquire for accurate availability Waterfront w/ a private heated pool & private dock just off Ockway Bay that leads to Nantucket sound. The home consists of 5 bedrooms with water views (3 king beds & 6 twin beds), 2 kitchen areas, 2 living areas, and 3 full bathrooms. Enjoy the peaceful private setting on the waterfront decks, swim in the pool, or kayak to the beach. Central A/C & 2 kayaks provided. Boats may be docked at our dock w/ owner permission

Sep 13 – 20

R16,308 ZAR per night

Guest favorite

Home in Oak Bluffs

4.93 out of 5 average rating, 169 reviews

Spectacular beach & pool combo; beautiful sunsets!

Close to airport, you’ll love backyard beach, water view, pool/grass yard, ambiance and the outdoors space. Beach & Pool (POOL HEAT STARTS SUMMER, 6/21) is a hard to find combination!! Location is private, yet it's close to the 3 largest towns on Martha's Vineyard. Great for couples, families (with kids), and big groups. Enjoy dinner with the indoor/outdoor Sonos music system during a beautiful sunset! NOTE; Rate increase in high season, pool/spa is a combined unit & ONLY heated in summer!

Mar 17 – 24

R10,732 ZAR per night

Guest favorite

Cottage in Sandwich

4.92 out of 5 average rating, 133 reviews

Blue Anchor Cottage - private hot tub getaway!

This newly renovated cottage is an amenity-filled launching point to explore all of Cape Cod! Just 0.4miles to the beach and with our own salt water pool, you’ll be able to fully enjoy the Cape's most historic town. Some of our favorites nearby: 2min- your local coffee shop 2min- great fish tacos + bar 2min- nice conservation area hike 2min- local convenience store 7min- downtown Sandwich 7min- golf course 9min- Sandwich Boardwalk 10min- Heritage Museums & Gardens 22min- Cape Cod Rail Trail

Oct 14 – 21

R6,397 ZAR per night

Guest favorite

Home in Sandwich

4.99 out of 5 average rating, 69 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!

Jan 8 – 15

R10,035 ZAR per night

Guest favorite

Apartment in Hyannis

4.89 out of 5 average rating, 102 reviews

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, and kettle. This studio has air conditioning.

Sep 29 – Oct 6

R3,480 ZAR per night

Guest favorite

Home in Edgartown

4.79 out of 5 average rating, 99 reviews

Katama gem.

Select Dog friendly, - mile from downtown, mile from south beach, steps to bike path, fenced in yard.. Gorgeous pool, w/a seperate pool house with flatscreen, mini fridge, and fold out queen. Downstairs the "cave", there is bar, pool/ping pong, flatscreen, pull out queen. Basic gym w/flatcreen.. Four bedrooms- one with private deck, and an upstairs office, five using very private pool house . The pool is sublime, hot tub is new, large yard, upstairs bathrooms with heated floors,

Jan 19 – 26

R9,686 ZAR per night

Superhost

Condo in Tisbury

4.91 out of 5 average rating, 45 reviews

Private 3bdrm Condo Tashmoo Woods

This 3 bedroom (3 king) 2 1/2 baths newly renovated condo is in a private setting with screened in porch. New kitchen, gas grill on deck, outdoor shower. -Access to the Tashmoo Woods Association pool, tennis courts and play ground. -Close to West Chop beaches. -Two miles from downtown Vineyard Haven. On bus route, but best to have a car. -The primary bedroom (king bed) is downstairs and the 2 upstairs bedrooms share a bath (shower only). Minimum rental 5 days, 1 week in summer.

Oct 8 – 15

R8,481 ZAR per night

Guest favorite

Home in Barnstable

4.93 out of 5 average rating, 104 reviews

Magical pool home with windmill/new kitchen

This magical, luxurious property has 6 bedrooms, 5 bathrooms & sleeping arrangements for 14 – it’s an excellent choice for a family, an offsite business meeting or a group of close friends looking for the ultimate beachside, pool experience with a four story windmill tower. The welcoming home has everything you’ll need for a comfortable stay, including wireless internet, central A/C, & a new pool. Its 4 story magical windmill will amaze you and your guests.

Nov 26 – Dec 3

R20,923 ZAR per night

Guest favorite

Guest suite in Centerville

5.0 out of 5 average rating, 44 reviews

Cape Cod Hideaway: Private Guest Suite with Pool

Enjoy a bit of Cape Cod in a quiet, safe neighborhood. Less than 1 mile from Centerville's convenience stores, and restaurants. Only 2 miles from Craigville Beach. Main street Hyannis is the "Hub" of the Cape and only a 10-minute drive away. 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. Book your stay today and experience the perfect vacation retreat.

Aug 15 – 22

R4,479 ZAR per night

Guest favorite

Home in Cotuit

4.91 out of 5 average rating, 11 reviews

ShoestringBayHouse, waterfront & pool in Cotuit

Welcome to ShoestringBayHouse, waterfront on Popponesset Bay. All rooms and decks overlook the beach & bay. We include: Bikes, Kayaks, and beach pass. Pool and Kayaks: approx May 15th - Oct 1st Our bay front home with 3 BR/ 3.5baths is perfect for a shoulder-season couples getaway or a short-term remote work location with multiple living-working areas. Our rate structure is designed for five adult guests plus small children.

Dec 4 – 11

R8,154 ZAR per night