Holiday rentals with a pool in Winona

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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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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!

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

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.

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!

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

Home in Winona
New place to stay

Walkable Retreat in a Historic Neighborhood

Enjoy this beautiful historic home just minutes from downtown. Relax by the private pool, unwind on the cozy patio, and soak up the charm of one of the city's most beloved neighborhoods. A peaceful retreat with an unbeatable location!

Popular amenities for Winona rentals with a pool

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