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 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

Feb 8 – 15

R3,322 ZAR per night

Guest favorite

Home in North Truro

4.93 out of 5 average rating, 97 reviews

Heated Pool, Beach, Pets, ADA, 5 bath, EV Charge

25X42 HEATED POOL. March 29th until Nov 29th 9am-9pm NO SERVICE FEE. 5 nights or more avail during Feb-March, inquire. SEASON- June 15th-Sept 7th (7) night min. SAT.-SAT. ONLY OFF SEASON- Sept 7th-June 17th (2) night min. Max heat setting 78 degrees. NO BALLOONS, PARTY, EVENTS, GATHERINGS, BRIDAL, WEDDING RECEPTIONS, MAX 12 for pool and dinners. Extra overnight guests = eviction and/or negates full sec. dep. return or $1500 additonal service fee. Sony PlayStation 4 w/Quintpack Jackbox Games

Feb 6 – 13

R17,563 ZAR per night

Guest favorite

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!

Nov 20 – 27

R5,265 ZAR per night

Guest favorite

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.

Jan 7 – 14

R2,801 ZAR per night

Guest favorite

Cottage in Provincetown

4.91 out of 5 average rating, 11 reviews

Beachside cottage with pool in Provincetown

Relax with family or friends at this cottage at Beach Point Club. Enjoy a BBQ on the large deck or walk to the beach on the private boardwalk, which is steps away from the cottage. Take in the water view from the side of the deck, hop on the shuttle to downtown Provincetown, or relax by the community pool. Bedrooms contains queen beds, and there are mini splits in the living room and bedrooms. Open-concept kitchen contains cooking basics and a Keurig. Linens provided. Pool open July-September

Feb 21 – 28

R5,600 ZAR per night

Guest favorite

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

R6,500 ZAR per night

Guest favorite

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 19 – 26

R3,622 ZAR per night

Guest favorite

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

Oct 7 – 14

R3,588 ZAR per night

Guest favorite

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.

May 10 – 17

R2,885 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.

Jul 12 – 19

R5,369 ZAR per night

Superhost

Apartment in Provincetown

4.9 out of 5 average rating, 10 reviews

Spectacular Waterfront Condo

Beautifully waterfront condo renovated in spring 2023. Newly appointed Kitchen features driftwood cabinetry with white quartz counters and center island. Enjoy water views from the kitchen/living room. New leather sofa and 65" TV in the loving room. The main bedroom features a king size bed and 43" TV and quest room appointed with a queen size bed and 43" TV. New bathroom features a walk in shower. Enjoy the sunsets on the deck or on the beach while enjoying an evening beverage.

Mar 27 – Apr 3

R5,450 ZAR per night

Guest favorite

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 16 – 23

R6,235 ZAR per night