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, 191 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
Cottage in Fish Creek
4.74 out of 5 average rating, 101 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.
Apartment 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 view of the Evergreen Hill Condominiums showcases a row of two-level condos set against a backdrop of green trees. The image features a fenced swimming pool with a cover and lounge chairs arranged nearby, creating a serene outdoor space.
Apartment in Fish Creek
4.91 out of 5 average rating, 284 reviews

Evergreen Hill A Whirlpool Condo by Pen State Park

It’s all about location and this is the perfect central location for your Door County adventure! A 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
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.
Apartment 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.
Apartment in Fish Creek
4.94 out of 5 average rating, 31 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.

Guest favourite
The living area features a spacious sectional sofa and a wood coffee table, with a striped area rug underfoot. A dining table with chairs is visible in the background, and a modern kitchen is seen through an open area. Soft lighting enhances the neutral decor.
Townhouse in Egg Harbor
4.93 out of 5 average rating, 166 reviews

Gorgeous Townhouse Condo-Indoor Pool and Hot Tub

Location, location, location! Unit 21 Townhouse style condo at Meadow Ridge Resort in Egg Harbor that is newly remodeled! Right at the top of the hill at the start of Egg Harbor. One mile to the newly expanded public beach. Half a mile away from downtown. Directly next door to Harbor Ridge Winery! This 4 bedroom end unit is one of the few at Meadow Ridge with no one above or below you and has direct access. Attached garage with gas grill. Large deck and backyard.

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.

Guest favourite
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.
Apartment 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.

Top guest favourite
A clear view of the in-ground swimming pool is framed by lush greenery and a well-maintained lawn. The sliding glass doors of the home are visible in the background, leading to a serene indoor-outdoor space with bay views.
Home in Oconto
4.97 out of 5 average rating, 135 reviews

Luxury Lakefront Home with Pool and Fire Pit

Welcome to our recently renovated Bay Getaway! We hope you can enjoy some slow paced time away and enjoy all that our Bay Getaway has to offer. The home offers panoramic views of the bay and all wildlife the bay brings, large heated in ground pool, hot tub, 125 inch theater quality 4k projector and screen w/ a Klipsch surround sound system, along with a fully stocked open concept kitchen to entertain large groups.

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.
Apartment in Egg Harbor
4.91 out of 5 average rating, 204 reviews

DoorCo Happy Place @Landmark Resort

Welcome to this relaxing, positive-energy resort! This 1-bedroom condo features a queen bed, queen sleeper sofa, and fully equipped kitchen, comfortably sleeping 4. Enjoy an indoor pool, exercise and game rooms in the main building, plus a hot tub and sauna in each building. Two heated outdoor pools (May–Aug), tennis court, playground, and walking trail are on site. RESORT FEE $10 + tax per day, paid at check-in.

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 £83 per night before taxes and fees

  • Verified guest reviews

    Over 400 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Wifi availability

    20 of Baileys Harbor holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Baileys Harbor rentals

  • 4.8 Average rating

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