Holiday rentals with a pool in Winona

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Winona

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

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Superhost

A spacious deck surrounds a large above-ground pool, featuring a safety railing and a shaded area from a large sun sail. Lounge chairs are positioned nearby, inviting relaxation in a peaceful outdoor setting.

Home in Onalaska

4.78 out of 5 average rating, 32 reviews

Secluded home w/pool, hot tub, cold plunge & sauna

Relax with the whole family at this peaceful place to stay. Seasonal large above ground pool 4 foot depth surrounded by deck with patio seating and sun shade (Memorial-Labor Day) Back patio features a private, lighted hot tub escape all year. Enjoy a fire near the chickens around our fire pit in a wooded, private area, an open back patio w/ seating, propane grill, smoker, trampoline and playground. Inside you’ll find a pool table, large gaming family room, foosball, dining seating for up to 15

Top Guest favourite

An indoor heated pool features a unique putting green within its waters. Large windows provide views of the surrounding greenery and the Mississippi River Valley. Potted plants adorn the corners, and two chairs are visible beside the pool area.

Home in Wabasha

4.97 out of 5 average rating, 76 reviews

Indoor pool-Arcades-Amazing Views!

This amazing property is nestled into the bluffs of the Mississippi River Valley, and is located on the fifth hole of The Bluffs at Coffee Mill Golf Course in Wabasha, MN. Enjoy an indoor, heated, endless pool that overlooks the Mississippi River Valley and is open for use year around. Play arcades, piano, outdoor games, sit by the firepit-firewood included and listen to the sounds of the fountain, or just enjoy the amazing views and wildlife from the deck, sunroom, dining room, or living room!

Guest favourite

A modern single-family home showcases a dark exterior with a spacious two-car garage. The front yard is neatly landscaped, featuring green grass and a young tree. A covered porch provides shaded entry, with large windows allowing natural light to stream indoors.

Home in Rochester

5 out of 5 average rating, 10 reviews

Unit 2365J | 2bd/2bth | Single-Family Home

Discover the perfect blend of comfort and convenience in our 2bd/2bth single-family home nestled in our safe, professionally managed community. This gem offers modern living with essentials like air conditioning, high-speed internet, and a fully equipped kitchen. Enjoy upscale amenities including a washer/dryer, smart-home technology, and a spacious 2-car garage. Plus, full access to a fitness center, outdoor pool, & BBQ area. All just a short drive from the Mayo Clinic. Your ideal home awaits!

Guest favourite

The exterior of a log home and guesthouse is depicted, showcasing natural wood finishes and stone accents. A spacious wrap-around deck offers seating areas and views of lush greenery. Two garage doors are visible beneath the main structure, complemented by a gravel path leading to the home.

Home in Alma

4.84 out of 5 average rating, 25 reviews

The Shack

Secluded Buffalo County log home & guesthouse. "The Shack" has 1 bathroom, master bdrm w a queen bed, large loft w 4 custom built twin beds, & guesthouse w a queen bed. Huge wrap around deck, gorgeous fireplace, incredible views, heated swimming pool & outdoor bar. Indoor slide for the kids! The property is over 75 acres with incredible hiking trails throughout. Make the trek to the top of the bluff & witness breathtaking views of the river & valleys around. A great kids treehouse also on site.

Superhost

A modern single-family home is depicted, featuring a sleek black exterior with a prominent garage. The driveway leads to a well-maintained lawn, flanked by young trees and ornamental grasses, creating an inviting entrance. Clear blue skies complete the serene setting.

Home in Rochester

5 out of 5 average rating, 3 reviews

Unit 2377J | 3bd/2bth | Single-Family Home

Discover the perfect blend of comfort and convenience in our 3bd/2bth single-family home nestled in our safe, professionally managed community. This gem offers modern living with essentials like air conditioning, high-speed internet, and a fully equipped kitchen. Enjoy upscale amenities including a washer/dryer, smart-home technology, and a spacious 2-car garage. Plus, full access to a fitness center, outdoor pool, & BBQ area. All just a short drive from the Mayo Clinic. Your ideal home awaits!

Guest favourite

A covered patio provides a view of a circular heated saltwater pool surrounded by a wooden deck. Lush greenery and rolling hills are visible in the background under a partly cloudy sky. Seating arrangements and potted plants are present on the patio.

Home in West Salem

4.86 out of 5 average rating, 14 reviews

Secluded Home With Unbeatable Views & Heated Pool

Come relax on this private, very secluded home that sits on 50 acres & features unbeatable views that’s just minutes from town. 3 bedroom, 3 full bath with an additional family room downstairs with pull out queen bed. Comfortably sleeps 8 (possibly 10). Outdoor amenities include heated saltwater pool with pergola/ shade, hiking trails, fire pit, trampoline, kids playset & grill. Smart TVs, office area, workout area, lg spacious kitchen & washer/ dryer are also features of this unique property.

Top Guest favourite

The exterior of the home is depicted, set against a clear blue sky. A spacious lawn surrounds the house, with lush green grass and trees framing the property. A deck extends from the house, providing an inviting outdoor space.

Home in La Crosse

4.99 out of 5 average rating, 84 reviews

3BR 3BA w/ Hot Tub, near LaX' Top Rated Activities

There are so many things that make this home a wonderful place to stay when visiting La Crosse. There is the hot tub year round and private pool in the warmer months which everyone will love! The whirlpool bathtub off the master is an added bonus. You will be in a quiet and safe neighborhood yet only minutes from downtown La Crosse, the ski hill, numerous parks, and some of the best fishing the Midwest has to offer. The south side is great because there is no traffic to deal with, ever!

Top Guest favourite

A serene outdoor space is highlighted by a stunning sunset over lush greenery. Comfortable seating is arranged around a fire pit, surrounded by blooming flowers and various plants. A swimming pool is visible in the background, nestled into the landscape.

Home in Rochester

5 out of 5 average rating, 47 reviews

RARE! Pool, hot tub, garden &chickens! 4m to Mayo

Our unique and tranquil getaway is just 3.7 miles from downtown Rochester! We have beautiful views of the sunrise & sunset, overlook hundreds of acres of forest & valleys, includes garden, chickens & amazing landscape. A few highlights: pool, hot tub, grill, smoaker, outdoor dining, fire pit, hiking, wildlife, Foosball, air hockey, trampoline, playground, bball hoop, treefort & more! We've been blessed with memories to last a lifetime and know you will at this secluded homestead too.

Guest favourite

A modern, single-story house is set among lush greenery, featuring a welcoming front porch with steps leading to the entrance. A driveway accommodates vehicles, while the yard is adorned with well-maintained grass and a variety of plants. Nearby structures are visible, contributing to the neighborhood's charm.

Home in La Crosse

4.97 out of 5 average rating, 33 reviews

Brand New, 3 Bed/ 2 Bath w/ Parking on UWL Campus

Centrally located this 3 bedroom, 2 bathroom house with parking available for three vehicles is PERFECT for all UW-La Crosse Events, OktoberFest & RiverFest. Enjoy being directly across from the UW- La Crosse Football / Track Stadium & just 1 block from Campus. A Park and Public Pool is also directly across the street and you're just 1 mile from downtown La Crosse. Home includes Washer & Dryer and outdoor patio / trampoline. Brand New & ready to enjoy!

Home in West Salem

4.67 out of 5 average rating, 3 reviews

A-Frame Pool House Hot Tub / POOL/ Sleeps 6

Beautifully remodeled A-frame cabin! This spacious home is nestled in the hills of West Salem, just outside of La Crosse and is perfect for a local stay-cation with friends and loved ones. Featuring 3 bedrooms, 2 full baths, open concept kitchen/living room, and downstairs rec space. Enjoy afternoons in the private backyard space, take a dip in the heated pool, and watch the stars from the hot tub at night! POOL OPENS JUNE 1 - September 1

Superhost

A modern living area features a grey sofa and a black accent chair, accompanied by two circular ottomans. A flat-screen television is positioned on a wooden console. Large windows allow natural light to fill the space, highlighting the neutral color palette and geometric area rug.

Apartment in Kutzky

4.87 out of 5 average rating, 15 reviews

One Bedroom Apartment

Located directly across from the Saint Mary's Hospital campus, the Berkman offers apartment style hotel units with modern furnishings and feels like your home away from home. This one bedroom, one bathroom apartment features residential appliances including an in unit washer and dryer, a queen sized bedroom and a sleeper sofa in the living room. Take advantage of top of the line amenities including a golf simulator and pool table.

A camper is situated beside a dirt path, with a wooden picnic table located nearby. Leafless trees outline the area, providing a natural setting. The ground is covered in dry foliage, and the space offers a semi-secluded atmosphere, enhancing the outdoor experience.

Campervan/RV in Zumbro Falls

4.75 out of 5 average rating, 4 reviews

Corner Lot Camper - Bluff Valley

This cozy rental camper sleeps up to 4 people, featuring a queen-size bed and two smaller bunks for a comfortable stay. Set on a great corner lot, it offers extra privacy and outdoor space to enjoy. With a compact kitchen, essential amenities, and a smart layout, it’s perfect for a hassle-free getaway. Enjoy comfort and convenience while making the most of your outdoor adventure! Camp site 606