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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Guest favourite
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
4.8 out of 5 average rating, 35 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

Superhost
Home in Onalaska
New place to stay

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.

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
4.98 out of 5 average rating, 80 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
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
Condo in Lake City
5 out of 5 average rating, 14 reviews

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.

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.

Superhost
Apartment in Rochester
5 out of 5 average rating, 4 reviews

Lux 1 BR I 1 Block to Mayo Skyway I Parking I Pets

Welcome to your luxury refined home base in the heart of downtown Rochester. Located at The Maven on Broadway, this upscale one-bedroom apartment offers the perfect blend of comfort, convenience, and elevated living—just a short walk to the skyway connecting you in minutes to the Mayo Clinic System. Whether you’re here for medical care, professional work, or supporting a loved one, this thoughtfully designed space provides a calm, stylish space with all the amenities needed during your stay.

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, 89 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!

Apartment in Rochester
New place to stay

Skyway connected Extended Stay in Rochester

With direct skyway access, Broadway Plaza is steps from Mayo Clinic. Apartments at Broadway Plaza feature spacious layouts with in-unit laundry, en-suite bathrooms, a half bath, and full kitchens. On-site indoor pool and gym offer places to unwind. Weekly housekeeping provides privacy and comfort. Note: Upon check-in, our front desk will capture a card and IDs for every adult to keep on file. A $500 security deposit will be taken for stays over 8 nights and returned if there are no damages.

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!

Guest favourite
Home in West Salem
4.94 out of 5 average rating, 17 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

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