Vacation rentals with a pool in Tisbury

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Top-rated rentals with a pool in Tisbury

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

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Guest favourite

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

Oct. 29 – Nov. 5

$405 CAD per night

Guest favourite

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.

Oct. 17 – 24

$1,751 CAD per night

Guest favourite

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!

Apr. 8 – 15

$1,132 CAD per night

Guest favourite

Home in Plymouth

4.92 out of 5 average rating, 170 reviews

Our Secret Garden

This beautiful 2.5 acre fully fenced in private property has gardens, an in-ground pool & pool house with an outdoor heated shower. Our home offers 2 kitchens, dining room seating 12, a great room, 3 bedrooms with private sitting areas & lower level with 2 bunk beds (bottoms are full beds) & exercise area. Outside are 2 grills & chiminea. We are 3 miles from the beach, shopping/cafes, 45 minutes from Boston (on a train route) and 20 minutes to Cape Cod. POOL can be HEATED for $500.00/Visit.

Sep. 17 – 24

$692 CAD per night

Guest favourite

Cottage in Sandwich

4.92 out of 5 average rating, 130 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

$573 CAD per night

Superhost

Home in Plymouth

4.9 out of 5 average rating, 212 reviews

Ocean Side, Amazing View, close to town/beach, Spa

PRICING IS FOR 2 GUESTS, 1 BEDROOM, 1 BATH ONLY, can add additional bed/bath for a fee, YOU WILL HAVE THE HOUSE TO YOURSELF and I only use this listing to fill gaps when the larger listing isn't rented-will decline ALL WEEKENDS, HOLIDAYS, PEAK times and will only accept mid-week, non summer/holidays. Please read additional info. OCEAN FRONT, HISTORIC SUMMER COTTAGE, AMAZING VIEWS, GREAT LOCATION, less than 1 mile walk to town and beach. Hot tub, fireplace, stocked kitchen, fresh linens.

Nov. 7 – 14

$886 CAD per night

Guest favourite

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.

Jul. 12 – 19

$484 CAD per night

Superhost

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,

Nov. 14 – 21

$1,213 CAD 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.

Apr. 18 – 25

$729 CAD per night

Guest favourite

Home in Middleborough

4.94 out of 5 average rating, 295 reviews

Private retreat setting on 4 acres 1

Gatherings, parties, events, reunions, etc. with 8 or more total sleepers /non sleepers MUST be discussed prior to booking. A 5 minutes from Rte. 495, secluded, 2 bedroom 1200 sq.ft. apartment. Amenities include -- in-ground pool, horseshoe pits, tennis/basketball court, fully lit for night time use. Central air, full bath, eat in kitchen, Juliet balcony, private drive & entrances, 2 HD flat screen TV"s, Netflix, On Demand WIFI. Very comfortable for two or a couple with children.

Apr. 18 – 25

$160 CAD per night

Guest favourite

Guesthouse in Falmouth

5.0 out of 5 average rating, 36 reviews

Falmouth/Woods Hole Charming Cottage By the Sea

Welcome to our Cottage By The Sea Rental located only minutes from the quaint village of Woods Hole, Falmouth and the Martha's Vineyard Ferry. We are located in the perfect setting to relax and enjoy all the area has to offer. Come enjoy The Shining Sea Bike path which is 10.7 miles , Sandy beaches, lively restaurants & local music scene, shopping on historic Main Street, Farmers Markets & more. Your sure to fall in Love with " Ole Cape Cod " when you visit our home and area

Jun. 19 – 26

$785 CAD per night

Guest favourite

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.

Sep. 29 – Oct. 6

$293 CAD per night