Vacation 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.

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!

Indoor Pool Home Theater Cabin & Arcade Lake Pepin

Escape to our Smart Home that we call The River Pools Cabin. This 5-bedroom, 2-bathroom retreat, is ideal for up to 16 guests. Enjoy a fully-equipped kitchen, cozy TV lounge, and a variety of entertainment options including board games and a game console. Relax in the private pool or hot tub, and savor outdoor dining with a fire pit and outdoor kitchen. Book now for a memorable getaway! We require that all guests sign our rental agreement that get's sent to you after you finalize your booking.

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.

Bear Creek Lodge w/ Pool and Hot Tub

This amazing lodge is exactly what you need for an unplugged getaway from your busy fast-paced lives. This acreage is right off a hard surface road outside Dorchester IA. Thousands of acres of public ground within minutes for hiking, hunting, and trout fishing. Upper Iowa River down the road for kayaking/tubing and the Mississippi River less than 20 min. Nothing says kick back and relax like a wrap around deck, wood burning stove, fire pit, grilling, pool, hot tub, and the famous NE IA bluffs!

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.

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.

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

Corner Lot Camper - Bluff Valley

This cozy rental camper sleeps up to 5 people, featuring a queen-size bed and 3 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