Holiday rentals with a pool in Racine

5 out of 5 average rating, 65 reviews

Home in Genoa City

Relaxing Getaway & Fall Fun near Lake Geneva

GET AWAY ✨ - Private backyard & cozy fire table, perfect for s’mores & memories. 🔥 - Oversized heated pool (Late May-Sep) - Near local skiing & tubing, Alpine Valley & Wilmot. ⛷️ - Gameroom w/ foosball, basketball & Simpsons bowling. 🏀🎳🕹️ - Near ziplining adventures & orchards. 🏞️ - Quiet neighborhood w/ baseball field, basketball courts & walking trail. ⚾️🏀🚶 - 15 min to Lake Geneva, 5 min to Richmond boutiques. 🚤 🛍️ - 1 hour to ORD/MKE/RFD airport. ✈️ - 40 min Six Flags & Great Lakes Navy Base 💦🎢🇺🇸

4.91 out of 5 average rating, 33 reviews

Villa in McHenry

Fabulous Cabin

WELCOME TO WATERFRONT LOG-SIDED HOME! ARTISAN CRAFTMANSHIP HOME OFFERS A BACKYARD OASIS SITUATED , NESTLED ON A PRIVATE POND, Heated POOL(closed till April 1st), Hot tub open from Oct 15th to Apr 15thGAZEBO, FIRE PIT, FISHING! 4 BEDROOMS AND 4.5 BATHS The homes sits on the highest point in the neighborhood and has stunning views in the front & backyard! Enjoy the mornings sitting on your front porch. The main floor is completed by an office, finished walkout basement in with a custom built bar

5 out of 5 average rating, 38 reviews

Apartment in Lake Geneva

Chic Condo in Lake Geneva.

Discover the freshly renovated one-bedroom condo at the charming Hayloft Lodge, located a few miles from downtown Lake Geneva. Unwind on the comfy couch, enjoy a restful night on the cozy queen bed, or head downstairs for a fun game of pool. This end unit features a kitchen with a mini fridge & freezer, a two-burner stove, a Keurig coffee maker, & more! The fitness area is available year-round, while the pool is open seasonally. A washer & dryer are conveniently located just outside your unit.

4.97 out of 5 average rating, 113 reviews

Farm stay in Germantown

Lace & Woods Farm "Hammer Hideaway"

HEATED POOL MAY-SEPT FOR ADDITIONAL CHRG. Cozy designer custom built guest house nestled amongst a 10 acre hobby farm. come for a relaxing getaway. This home is an artistic gem! Boasting an open concept, with a queen bed on main level and twin mattress underneath , a full kitchen, cozy living area, wood burning fireplace. The loft has extra sleeping with a double bed and twin bed.Custom designed. Great location winter and summer, enjoy snowmobiling trails and skiing near by or beaches & hiking

4.89 out of 5 average rating, 125 reviews

Home in McHenry

Highwood Haven/Indoor Pool/Hot Tub/Arcade

Unwind at Highwood Haven, an opulent McHenry getaway with a heated indoor pool and arcade. Savor culinary delights in our chef's kitchen, enjoy al fresco entertainment, and relax in sumptuous bedrooms. An hour from Chicago, it's ideal for luxury retreats and family fun. Revel in our nine-person hot tub, outdoor lounge with TV, and serene bedrooms. Make memories with both lively entertainment and tranquil moments, all within a luxurious setting. Your perfect destination for an upscale vacation.

5 out of 5 average rating, 36 reviews

Home in McHenry

Paradiso Vacation

Welcome to our home, a sanctuary of comfort, and unique design. This house it's a perfect blend of modern amenities and timeless elegance. The living area features a cozy fireplace, ideal for family gatherings. The kitchen is equipped with top-of-the-line appliances. The master suite is a private retreat, with walk-in closets, vanities, and a shower. A unique feature of this home is the outdoor living space, with a pool, jacuzzi and BBQ grill making it perfect for entertaining or relaxing.

4.84 out of 5 average rating, 395 reviews

Chalet in Ingleside

"A" Frame Brandenburg Lake

Getaway to a cozy 1 bedroom w/loft for 2, up to 6 people. Full kitchen 1.5 bath all season getaway. There is a piano as well. A tranquil home steps from a private lake. Oak and Pine surround you plus a stone fireplace, it feels like the North Woods. The A Frame guest house shares a 5 acre compound ( total 20 Acres) with the owners residence and caretaker cottage. The Volo Bog 800ft away. No hot tub Nov - May. Swimming pool, June-October often cool to use in early June.

5 out of 5 average rating, 18 reviews

Home in Lake Geneva

Lake Geneva Home w/ Pool near the Lake!

Lake Geneva home with private in-ground pool just 2 blocks from lake, beach and pier! .5 Acre yard loaded with tons of gathering places, hammocks, games and activities for everyone. This folk art filled home has 2 queen, 1 king, and 6 twin beds that can comfortably accommodate 12 guests. The home is completely renovated with many areas for games, reading a good book, or sitting by the fire. Chef's kitchen and weber grill to create beautiful memories with the group!

4.81 out of 5 average rating, 36 reviews

Boat in Racine

Vessel: The Friendship - Classic Egg Harbor E5-3

Enjoy Marina life at Reefpoint Marina. Close to the beach and on the water with this Classic Egg Harbor yacht is filled with character. The “Friendship” can sleep 6, however we encourage no more than 4 guests. (1 Stateroom (Sleeps 2), Dinette and sleeper sofa convert to doubles in the salon) - Enjoy beautiful sunsets and sunrises, a cool lake breeze and star gazing at night. Pools scheduled to close 9.26.22 (Will reopen in Spring 2023 when weather permits)

4.93 out of 5 average rating, 15 reviews

Flat in West Allis

Modern Apartment/ 8mins to Stadium/ Parking

✨ Modern & Cozy Stay in the Heart of West Allis ✨ Stylish, light-filled apartment just steps away from the State Fair Grounds! Enjoy a cozy living room, fully equipped kitchen, peaceful bedroom, and access to a pool & lounge areas. Perfectly located near dining, shopping, and entertainment — right in the heart of West Allis, only steps away from the State Fair Grounds. 10 mins to Downtown Milwaukee 7 mins away to American Family Field

4.93 out of 5 average rating, 163 reviews

Home in Lake Geneva

Home away from Home

Our cozy and inviting home is designed for relaxation and fun, offering a wide range of amenities to make your stay unforgettable. Enjoy a refreshing dip in the in-ground pool, cozy up by the fireplace, or challenge your friends and family in the game room. just a short walk from the downtown area with shops, restaurants, and attraction all while enjoying the peace and comfort of a relaxing retreat. We look forward to hosting you!