Vacation rentals with a pool in Wellfleet

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Top-rated rentals with a pool in Wellfleet

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. 31 – Nov. 7

$374 CAD per night

Guest favourite

Condo in Brewster

4.97 out of 5 average rating, 158 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!

Jan. 2 – 9

$431 CAD per night

Guest favourite

Apartment in Wellfleet

4.97 out of 5 average rating, 34 reviews

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.

Oct. 12 – 19

$249 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!

Dec. 21 – 28

$1,164 CAD per night

Guest favourite

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

Sep. 5 – 12

$754 CAD per night

Guest favourite

Camper/RV in Wellfleet

5.0 out of 5 average rating, 20 reviews

Seasonal 27’ Retro Glamping Steps From Bike Trail

A SECLUDED WELLFLEET LOCATION, STEPS FROM BIKE PATH WITH DELIGHTFUL AMENITIES. This 27’ Camper with many upgrades, and shared 18X30 pool is located in a peaceful setting on private property (with Host’s Home set back ) just steps from the Cape Cod BikeTrail and Hiking Trails. Location will especially appeal to Avid Cyclists, as well as Beach Goers and people looking to enjoy activities in beautiful Wellfleet. The Atlantic Ocean Beaches are car or bike accessible 5-10 minutes away.

Jan. 26 – Feb. 2

$343 CAD per night

Guest favourite

Condo in Truro

4.82 out of 5 average rating, 51 reviews

Designer Studio Condo with peeks of Cape Cod Bay.

MEMORIAL DAY WEEKEND SPECIAL, 15% Discount! See 'my property'. Beautiful, unique designer condo. Photos show what makes my place stand out from others. Please view and read captions ! 10 minute walk to Bay beach, 10 minute drive to Provincetown. Peeks of blue bay from private, spacious deck. Near Atlantic beaches, Truro vineyards, historic lighthouse & Wellfleet. Quiet in unit, 2nd floor, no one above. Guests 21+ welcome, 3 night minimum 5/20 to 6/27 check ins, 4 nights 6/28 to 9/1 check ins

May 16 – 23

$301 CAD per night

Guest favourite

Cottage in Provincetown

5.0 out of 5 average rating, 9 reviews

Cozy Cottage in the East End

Cozy cottage nestled in the East End of Provincetown. Enjoy this prime location just under a mile from the center of town. Plenty of shops, restaurants, galleries and activities to enjoy! Relax in our newly, fully renovated home complete with private patio and two parking spots! Outdoor dining and living areas provide even more space for you to enjoy outside. Steps to the convenient East End Market & Cafe, Berta Walker Art Gallery and Provincetown Theatre. You're guaranteed a great vacation!

Jan. 11 – 18

$451 CAD per night

Guest favourite

Apartment in Dennis

4.88 out of 5 average rating, 16 reviews

Pool condo in Dennis Village, 4 mins to Mayflower

Relax in this calm, stylish, new, fully equipped 1 BR condo. “Cape Storia d’ Amore” is 4 mins from Mayflower in the heart of Dennis Village. Located less than 5 minutes from The Merc, Scargo, Oliver's & Planck's Tavern & more. 12 minutes from Cape Cod Inflatable Park. Large, fully enclosed pool is just steps away. new: - kitchen with new range, DW, fridge, Keurig/drip coffee maker, cookware. New bathroom w/walk in shower, washer & dryer. Smart TV, Roku, internet, fireplace, AC in summer.

Oct. 17 – 24

$281 CAD per night

Guest favourite

Home in Plymouth

4.9 out of 5 average rating, 213 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.

Apr. 4 – 11

$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.

Sep. 29 – Oct. 6

$330 CAD per night

Guest favourite

Cottage in Wellfleet

5.0 out of 5 average rating, 18 reviews

Sandpiper Cottage

Sandpiper is a three bedroom air conditioned cottage rented with linens and daily maid service. This cottage has three separate bedrooms- one queen bed with TV, one double bed, and two twin beds with TV. The open living area features a flat screen TV with a DVD player and a comfortable eating area. The kitchen includes a full-size refrigerator, oven, microwave, toaster, coffeemaker, pots and pans and dishes. Outside, there is a private deck with a picnic table and a gas grill.

Sep. 23 – 30

$526 CAD per night