Holiday rentals with a pool in Baileys Harbor

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Top-rated rentals with a pool in Baileys Harbor

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

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Guest favourite
A spacious living area is highlighted by a large sectional sofa, accented with decorative pillows. A flat-screen TV is mounted above a stone fireplace. Natural light pours in through two large windows, enhancing the welcoming ambiance of the space.
Townhouse in Egg Harbor
4.9 out of 5 average rating, 187 reviews

Indoor pool and hottub Egg Harbor condo #51

Townhouse condo at Meadow Ridge Resort in Egg Harbor. 1/2 mile from downtown Egg Harbor and the Egg Harbor Fun Park. This condo has 3 bedrooms, master has king size bed, 2nd bedroom has 2 full size beds and the 3rd bedroom is a loft that has a King size bed. Living room also has a pull out sofa. 2 1/2 bath. Also has an attached 1 stall garage with a gas grill. Upper and lower deck. New beds and TVs. There is a pool house featuring an indoor pool and hottub located at the Meadow Ridge entrance.

Superhost
The living area features large windows, allowing natural light to filter in, illuminating the comfortable seating area. A wooden dining table is set with placemats, and a chandelier hangs above. A small balcony is visible through the sliding glass doors.
Condo in Egg Harbor
4.93 out of 5 average rating, 198 reviews

DoorCo Happy Place @Landmark Resort

Welcome to this wonderful, full of positive energy and relaxing resort! The condo is a great place to relax, explore and rejuvenate! 1 bedroom with a queen size bed and queen sleeper sofa in the living room and fully equipped kitchen make enough room for 4 guests. The resort is a great place to enjoy- 1 indoor pool, exercise room and a game room located in the main building, hot tub, sauna in each building, 3 HEATED outdoor pools open seasonally (May- August), tennis court, playground, a trail.

Guest favourite
A tri-level condo complex is nestled among lush greenery, showcasing multiple balconies and staircases leading to the main entrance. A pool area is visible in the foreground, where lounge chairs are arranged around a covered pool. The serene landscape adds to the peaceful ambiance.
Condo in Fish Creek
4.86 out of 5 average rating, 307 reviews

Evergreen Hill B Whirlpool Condo by Pen State Park

It’s all about location and this is the perfect central location for your Door County adventure! All 4 B rental condos are set on a lovely, peaceful street in Fish Creek. On warm days, enjoy hiking, swimming, biking, boating, camping, picnicking, fishing, and golf. When snow is on the ground, spend time cross-country skiing, snow shoeing, snowmobiling, and sledding. Daily housekeeping is not included. You can add it for $24 per day if you would like, just let us know when you pick up your key.

Guest favourite
A spacious living area is presented, featuring a large sectional sofa and an accent chair. Natural light filters through multiple windows. The adjoining dining area includes a long table surrounded by several chairs. A view of the modern kitchen with dark cabinetry is visible in the background.
Townhouse in Egg Harbor
4.93 out of 5 average rating, 164 reviews

Beautifully Updated Egg Harbor Townhouse in town!

Awesome location and beautifully updated Unit 52 Townhouse style condo at Meadow Ridge Resort in Egg Harbor. Right at the top of the hill at the start of Egg Harbor. One mile to the public beach, 1/2 mile from downtown. Directly next to Harbor Ridge Winery! This 3 bedroom, 2 living room unit is one of only a few at Meadow Ridge with no one above/below and has direct access-no hotel style common area. Attached garage with gas grill. Large deck. Indoor pool and hot tub in clubhouse!

Top Guest favourite
A serene landscape features a one-acre pond surrounded by lush greenery and colorful autumn foliage. A charming barn and the main lodge are visible in the distance, creating a harmonious blend with the natural setting.
Barn in Wallace
4.97 out of 5 average rating, 39 reviews

Pinewood Springs Lodge, 240 acres with 1 acre pond

Beautiful antique barn restored with all pine wood interior. Downstairs are four unique bedrooms each with its own full bathroom. Upstairs is an open concept communal area with kitchen, dining area, pool table, wood stove, TV area, and fireplace. Large paved parking and turnaround area, perfect for vehicles with trailers. Between the lodge and 1 acre pond is an apple orchard and open farm fields. Enjoy privacy and seclusion, the perfect opportunity for enjoying moonlit starry nights.

Guest favourite
The entrance to Meadow Ridge is marked by a stone facade featuring two blue signs. Surrounding greenery is complemented by pumpkins arranged on a stone outcrop, creating a seasonal display. Soft light illuminates the scene, highlighting the welcoming aspect of the property.
Condo in Egg Harbor
4.91 out of 5 average rating, 112 reviews

Entire Townhouse -Escape to Door County

Unit F22 in Meadow Ridge is just a minute away from beautiful Egg Harbor! You’ll stay in a quiet townhouse with no one above or below you, with private parking and entrance. There is a gorgeous indoor pool, indoor hot tub, tennis court, and walking trail onsite. Right next door to Harbor Ridge Winery, minutes from fine dining, boutique shopping, a beautiful marina and beaches in quaint Egg Harbor. Down the road from an adventure park with go-karts, mini golf, arcade games and more!

Guest favourite
An inviting outdoor pool area features a sparkling blue pool and a relaxing hot tub. Surrounding lounge chairs and tables offer a place to unwind, while the well-maintained landscaping provides a serene backdrop. The townhome structure can be seen in the distance.
Condo in Fish Creek
4.93 out of 5 average rating, 30 reviews

Fish Creek Condo - Walk to Shopping, Dining & Park

Nestled in the heart of Fish Creek, the Hilltop Retreat offers the perfect blend of tranquility and convenience for your next Door County adventure. This charming two-bedroom, 1.5 bathroom townhome is just a short walk or bike ride from local shops, restaurants, and the breathtaking Peninsula State Park. Whether you're here for a relaxing escape or an action-packed getaway, this well-appointed condo delivers exceptional hospitality with top-tier cleanliness and comfort.

Superhost
A light-colored mobile home is positioned under leafy trees, showcasing a wooden deck with a railing. Picnic tables are arranged nearby on a grassy area, providing an outdoor space for relaxation and enjoyment.
Cabin in Baileys Harbor
5 out of 5 average rating, 10 reviews

D’ Cabin 3

Your family will be close to everything when you stay at this centrally-located place. 5 -10 mins on Door County’s famous little towns a mile to lake Michigan and great restaurants. This cabin is part of Beantown Campground rentals all amenities offered can be use by the guest of this cabin we do allow pets on this rental but we do have other ones we do. This is set up for camping so bring linens towels pillows cooking stuff and utensils the guest needs to bring.

Superhost
A living area features a comfortable red sofa facing a large window that offers views of green outdoors. A gas fireplace is positioned beside a light wood shelf with decorative items. A TV is mounted on the wall, and a patterned chair and coffee table complete the setting.
Apartment in Fish Creek
4.84 out of 5 average rating, 70 reviews

1 Bedroom Suite in a World-Class Swedish Resort

Little Sweden offers hiking, biking, cross-country ski trails, championship golf courses, fishing, windsurfing, boating, state parks and summer theater. Historic villages along the Door Peninsula abound with an array of antique shops and art galleries. All amenities open. • Guest checking in must be 18+ with valid ID & credit card for $250 refundable security deposit (credit card only) • Name on reservation must match photo ID at check-in

Superhost
The living area is furnished with a gray sectional sofa adorned with blue and patterned cushions. A wooden coffee table sits on a textured blue area rug, with a small plant placed on top. The open kitchen is visible in the background, featuring modern appliances and a dining island with seating.
Condo in Egg Harbor
4.88 out of 5 average rating, 178 reviews

Condo Indoor Pool Meadow Ridge #23 Egg Harbor, WI

Condo F23 at Meadow Ridge Resort in Egg Harbor, remodeled in 2022. Directly at the top of the hill at the entrance to Egg Harbor. One mile to public beach and half a mile from downtown. This 1800sqft, 3 bedroom unit is one of few at Meadow Ridge with no one above or below you and has direct access versus a common entrance. Attached single stall garage with gas grill and four beach chairs for guest use. Large deck and backyard.

Guest favourite
A spacious heated pool area is surrounded by trees showcasing autumn foliage. A water slide is positioned at one end, while seating options include lounge chairs and a shaded umbrella table. The pool deck features a mix of colorful accessories, enhancing the outdoor experience.
Home in Sturgeon Bay
5 out of 5 average rating, 9 reviews

Cottage at Cave Point - Private pool+Arcade

Cave Point Cottage is the is the perfect place for groups to enjoy Door County. Nestled on 6 acres of land, we offer 6 spacious bedrooms, 3.5 baths, a heated pool* + FREE arcade room and a large garage with a screen to enjoy the outdoors while playing a game of ping pong. We offer wireless internet, 2 large TV rooms, whirlpool tub, a walk- in shower, a beautiful sunroom, furnished kitchen with 2 refrigerators and a washer/dryer.

Guest favourite
A bright living area features large windows that offer views of the surrounding landscape. A comfortable brown leather sofa and an accent chair are arranged around a dark coffee table. Natural wood ceiling beams complement the warm green walls, creating a cozy atmosphere.
Cottage in Fish Creek
5 out of 5 average rating, 9 reviews

Harbor Cottage | Downtown Fish Creek-Dog Friendly

Escape to Harbor Cottage, a charming 1BR/1BA retreat with views of Fish Creek Harbor. Walk to downtown shops, dining, and Peninsula State Park, or relax in cozy décor with a full kitchen and living space. Enjoy the seasonal heated pool (Memorial Day–Labor Day) and all the comforts of home. After booking, a $500 security deposit and signed rental agreement are required.

Popular amenities for Baileys Harbor rentals with a pool

Quick stats about holiday rentals with a pool in Baileys Harbor

  • Total holiday rentals

    Explore 20 holiday rentals in Baileys Harbor

  • Nightly prices starting at

    Baileys Harbor holiday rentals start at $170 AUD per night before taxes and fees

  • Verified guest reviews

    Over 370 verified reviews to help you choose

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Wi-Fi availability

    20 of Baileys Harbor holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Baileys Harbor rentals

  • 4.8 Average rating

    Baileys Harbor stays are highly rated by guests—averaging 4.8 out of 5!