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
4.91 out of 5 average rating, 190 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.

Guest favourite
A charming outdoor patio area is presented with a small dining table and black chairs, shaded by an umbrella. Planters with greenery adorn the space, which is surrounded by grass and trees, creating a serene environment for relaxation.
Place to stay in Sister Bay
4.86 out of 5 average rating, 36 reviews

Cottage on SisterBay Inn grounds

Relax at this peaceful and unique place to stay. Just a half mile away from downtown beautiful Sister Bay Located on Sister Bay Inn grounds including outdoor heated pool (May24-Sep5) hot tub, firepit, fitness room and basic continental breakfast! King studio sweet (all open space) gives you privacy tucked away by the meadows while enjoying all Sister Bay Inn amenities. To access the cabin, you are required to walk down the full flight (15) stairs from the parking lot. We do not have an elevator

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
4.92 out of 5 average rating, 201 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, 315 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.

Superhost
Cottage in Fish Creek
4.74 out of 5 average rating, 100 reviews

Cozy Cabin! Amazing Location in Fish Creek! Pool!

Little Yellow Cottage is in the heart of Downtown Fish Creek. Featuring 2 cozy bedrooms, living room, full kitchen, 3 Roku-TV's, wifi, whirlpool tub/shower, & outdoor swimming pool. Enjoy the off-site "Adventure Shed" bikes and kayaks to use at Peninsula State Park or surrounding areas. We have a grill, coolers and games! Located just steps from Peninsula State Park, Sandy Fish Creek public beach, & the best local restaurants. Kid & dog friendly. *Please read description in full before booking*

Guest favourite
A view showcases a well-appointed home nestled among vibrant green trees, with hints of autumn colors. The surrounding landscape gently slopes toward a serene lake, reflecting the lush greenery and clouded sky.
Condo in Sister Bay
5 out of 5 average rating, 19 reviews

Peaceful Nature Retreat! Short Walk 2 Pebble Beach

All newly furnished and fresh! Cozy fresh linens and furnishings that make you feel like this is your "Home Away From Home". This condo is tucked just 1 mile south of Sister Bay. It is located on a private setting adjacent to Bay Ridge Golf that is now a natural area, home to many happy wildlife residence. This peaceful setting is a 10 minute walk to serene Pebble Beach. Come escape and relax in our quiet setting -walk the trails & quiet country roads. Refresh with a dip in our pool.

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!

Superhost
A spacious living area showcases a modern sofa and armchair, complemented by a wooden coffee table. A stone fireplace is centered beneath a large TV displaying a scenic sunset. Natural light fills the space through windows, enhancing the contemporary design.
Home in Fish Creek
4.8 out of 5 average rating, 10 reviews

Shore Suite | Downtown Fish Creek ~ Dog-friendly

The Shore Suite is a newly designed 2BR/2BA duplex at Spruce & Shore Motel. Featuring all-new furniture, luxury bedding, it’s the perfect blend of style and comfort. Walk to shops, restaurants, or explore Door County. Enjoy a king bed with ensuite bath, a seasonal heated pool (Memorial Day–Labor Day). After requesting your reservation, you will receive a notification to submit a security deposit of $500 and complete our Rental Agreement, confirming the terms and conditions of your stay.

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
4.91 out of 5 average rating, 11 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.

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 $164 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!