Vacation rentals with a pool in Baileys Harbor

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

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*

DoorCo Getaway@Landmark Resort

2-bedroom condo at the Landmark Resort in the heart of Door County, set on 40 wooded acres. Guests enjoy an indoor pool, 2 heated outdoor pools (May–Oct), hot tub, sauna, casual dining, bay-view common areas. Amenities include a fitness center, tennis, basketball, pickleball, shuffleboard and volleyball courts, playground, hiking trails, restaurant, outdoor gas grills, EV charging, laundry facilities, and free parking. Condo includes AC. PLEASE NOTE: $10 resort fee+tax per day due at check-in.

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.

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.

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.

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!

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!

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.

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.

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.

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.