Holiday rentals with a pool in Winona

Backyard Oasis w/ In-Ground Pool, FirePit & Gazebo

Experience refined comfort in this fully renovated 5-bedroom home located in the heart of town. This fully renovated home was designed for comfort, connection, and unforgettable stays. Perfect for entertaining, it features an open-concept layout, spacious kitchen, large dining table, and a wood-burning fireplace. Step outside to a private, fenced backyard with an in-ground pool, screened porch, fire pit, expansive 20x12 gazebo—an ideal setting for relaxation, family time, and upscale gatherings.

Main Floor Cabin (sleeps 4)

Cabin 4 at the Sunset Motel is a freshly updated unit with a flexible, semi-open layout. One side features a king bed, big-screen Smart TV, cube storage, and wall hooks for convenience. A partial wall with an open walkway separates this area from the common space, which includes a sleeper sofa (sleeps one or two) and an additional Smart TV—great for relaxing after a day of exploring. The bathroom has a walk-in shower and toilet with a door for privacy, and the sink and vanity are located just o

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!

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.

NEW! Renovated Escape w/ A+ Location, Views & 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 (up to 12). Outdoor amenities include heated saltwater pool w/ pergola/ shade, hiking trails, fire pit, trampoline, kids playset & grill. Smart TVs/ Starlink, workout area, newly renovated spacious kitchen & washer/ dryer are features of this unique property.

3 Bedroom Condo - Sleeps 6 (upper level)

This apartment is a part of the Sunset Motel located directly across from Lake Pepin in Lake City, MN. The hotel consists of traditional single and double motel rooms, a 3 bedroom house, and 2-3 bedroom condo units. All of the units have shared access to our heated in-ground pool. All rooms have recently been equipped with electronic locks for a seamless check-in process. Located near some of the area's best attractions including public beach access, top restaurants, golf courses, and marinas.

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!

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!

Tiny Home

Enjoy tiny home living with extra comfort at Camp Everyday. This spacious little getaway includes a bedroom, 2 bed loft, full bath, kitchen, dining area, and relaxing living room with beautiful windows. It is a great spot for families, couples, or anyone wanting a unique campground stay near Win Enjoy the sounds of nature when you stay in this unique place. All camp ground amenities including, including Pool between memorial and labor day weekends.

A-Frame Wellness Retreat | Pool• Hot Tub• Full Gym

Secluded A-frame cabin in the trees, cozy vibes with a full wellness setup for a reset. Morning coffee on the expansive deck, afternoons by the private pool (open June 1–Sept 1), evenings in the hot tub under the stars. Indoor fitness area: squat rack, dumbbells, rowing machine, yoga mats + open floor. Perfect for reset weekends, group getaways, or extended stays. POOLS OPEN JUNE-SEPTEMBER 1

2 Bedroom Condo - Sleeps 6 (upper level)

This updated 2-bedroom condo is perfect for families or groups, with a full kitchen, dining room, and living area that opens onto a large deck overlooking the pool and Lake Pepin. One bedroom has a king bed and storage, and the second has two queen beds and a closet. Located on the second floor with exterior stair access, it's ideal for longer stays or quick getaways.

3 Bedroom home (sleeps 8)

This cozy bungalow is part of The Sunset Motel property, just across from Lake Pepin. It features a covered porch, grassy yard, and three upstairs bedrooms (queen + full, full, and bunk beds) with a full bath. All guests enjoy access to the heated pool and self check-in. Great for families or small groups, and close to beaches, restaurants, marinas, and more.