Holiday rentals with a pool in Baileys Harbor

Find and book unique homes with a pool on Airbnb

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 £96 per night before taxes and fees

  • Verified guest reviews

    Over 420 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!

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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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
4.93 out of 5 average rating, 15 reviews

D’ Cabin 3

Welcome to your perfect dog-friendly getaway—where comfort meets the great outdoors. Our 2bedroom cabin is designed for both you and your four-legged companion to relax, recharge, and explore together. This located in Beantown Campground so the guest can enjoy the amenities the campground has to offer. You do need to bring you linens towels blankets pillows cooking and eating utensils. This is located in the heart of Door County town of Baileys Harbor 5-10mins to enjoy scenery, beach and more.

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
4.88 out of 5 average rating, 40 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

Guest favourite
Townhouse in Egg Harbor
4.91 out of 5 average rating, 201 reviews

Newly remodeled Indoor pool/hottub Egg Harbor #51

Newly remodeled Townhouse condo at Meadow Ridge in Egg Harbor. New pictures coming soon. 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 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. Poolhouse features an indoor pool/hottub located at the Condo entrance.

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, 23 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, 301 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
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
4.94 out of 5 average rating, 173 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!

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
4.98 out of 5 average rating, 44 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.
Apartment in Egg Harbor
4.91 out of 5 average rating, 125 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
A spacious living area features a large, L-shaped sectional sofa in a soft gray hue, complemented by a square ottoman. Natural light fills the space through multiple large windows overlooking the green landscape. A dining area is visible in the background with table seating.
Home in Sturgeon Bay
4.94 out of 5 average rating, 17 reviews

Door County Agrotourist Retreat

Experience peaceful country living with modern comfort at the Dead End Oasis — a spacious 5-bedroom farm retreat in Door County. With an outdoor pool, cozy fire pit, on-site cows, and no cleaning fee, it’s perfect for families, friend groups, or just a breath of fresh country air. Just 3 minutes from Renard’s Cheese and close to Sturgeon Bay attractions, this unique stay offers a true taste of farm life — with all the extras you’ll love.

Guest favourite
Apartment in Egg Harbor
4.84 out of 5 average rating, 79 reviews

Updated Townhouse Condo with Indoor Pool & Hot Tub

Keep your group together in this great townhouse-style condo that sleeps up to 12. Enjoy swimming year round with an indoor pool and hot tub. Unit is equipped with high-speed internet and smart TVs in each room. Conveniently located at the entrance to downtown Egg Harbor, just off Hwy 42. Door County Room Tax and Wisconsin State Sales Tax are in addition to rental costs shown. DOOR COUNTY TOURISM ZONE PERMIT NUMBER: #0953266900

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, 187 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 living area features a gray sofa adorned with two light blue cushions, paired with a round wooden coffee table. A comfortable armchair is situated nearby. Large windows allow natural light, and a stone fireplace adds to the inviting ambiance.
Townhouse in Egg Harbor
4.84 out of 5 average rating, 105 reviews

*Indoor Pool * Egg Harbor Townhouse Condo Unit 50.

Location, location, location! Unit 50 Townhouse style condo at Meadow Ridge Resort in Egg Harbor. One mile to the newly expanded public beach. Half a mile away from downtown. Close to much more. This 3 bedroom unit is unique because it has no one above or below you and has direct access to a common area. Unit also has garage, gas grill, upper and lower decks, and smart TVs in all the bedrooms and living room.

Popular amenities for Baileys Harbor rentals with a pool