Holiday rentals with a pool in Racine

Great Lakes Family Getaway

Wonderfully remodeled multi-level home ideal for Navy Graduation visits or regional travel—situated between Chicago and Milwaukee. With 3 bed/2 baths upstairs and 1 bed/1 bath on the lower level, there's room to spread out. You'll truly enjoy time with your loved ones in this beautiful home with a large yard that backs up to a golf course and includes a game room, screened porch and in-ground pool (weather permitting). 8 mi. from GL Navy Base and 5.5 mi. from City of Hope Cancer Treatment, Zion

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

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.

Family-sized Indoor Heated Pool & Movie Theater!

**HUGE INDOOR HEATED POOL**THEATER**SLEEPS UP TO 18 MAX** Set on a private and quiet property, this home boasts a 24/7/365 huge heated indoor in-ground pool attached to the house that is yours to use exclusively throughout your stay! The house has a private movie theater and fully stocked gourmet kitchen! Our occupancy is 18 max visiting or staying. Bring your well-behaved, house-trained dog to join you for no additional fee! **30 day rental available** You will not be disappointed!

BRAND NEW 3 Bedrooms, Grill, 70 inch TV, KING Bed!

Note before booking: We are anticipating the final window shades to primary bedroom to be installed first week of 2026. There is ongoing construction in the community. The Wonder: A Brand-NEW 3BR, 2.5BA townhome in the private Stonewater Community! Peaceful, pet-friendly, and perfectly located near McHenry, Wonder Lake, and Woodstock with easy access to Chicago. Sleeps 8, features a 2-car garage, baby gates, and summer pool access. On-site gym coming soon. Your modern retreat awaits!

Big BLUE Skyline VIEW

This bright and roomy 2 bedroom unit is the lower level of a 1900 Victorian duplex in the heart of Milwaukee was renovated 3 years ago. Situated on the edge of downtown, overlooking the river and downtown skyline you’ll have easy walking access to all the best neighborhoods. With 9 foot ceilings and a big fenced in yard with basketball hoop and patio furniture you'll be very comfortable staying with us. We are not a corporation, just a nice couple sharing our place. FREE PARKING too

7 1/2 Acre Private Estate MSG Owner for Discounts

Any event needs to be approved. First 4 guests 10 y/o and up are included in the nightly rate. Then I charge per person per night over 4 guests. PETS ALLOWED FOR $200.00 3 Bedroom, 3 Bathroom, 3000 Sq/ft Heated Pool!!, Hot Tub!!, Fishing Pond!!, Game Room all on 7 1/2 Acres!!!!!! It is a ONE OF A KIND!! NEW REC ROOM!! 1/2 Acre Fishing pond Stocked with MANY FISH!!! Sand Beach and Pier with boat, Paddle Boards. heated in ground pool, (open May1 - October 1st), hot tub.

#EnglishPrairieBnB | 4 Bedrooms | 2.5 Baths

🔒💵 Note: $1,200 Host Safety Deposit required directly after booking. 📄📌 Terms and Conditions below. ✨ Cozier EnglishPrairieBnB! ✨ Enjoy our ‘lite’ version 🌟—a smaller option for up to 8 guests, offered last-minute when the 🏠 8-bedroom listing is unsold. 🌼 Perfect for Gatherings Experience the charm of EnglishPrairieBnB in a cozy, streamlined setup. 💵 Pricing Note This listing’s pricing is higher 21+ days out to prioritize larger groups for the 🏠 8-bedroom option.

"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.

Modern Apartment/ 8mins Downtown/ Parking/Pool/Gym

✨ 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

Beautiful 6 bedroom with Heated Pool & Jacuzzi

Relax with the whole family at this peaceful place to stay right in the middle of beautiful Whitnall Park. You won't find a more peaceful view of the woods and park. Our beautiful home has a large heated pool with brand new 6 person jacuzzi. Brand new Kitchen and updated bathrooms. Master suite is very romantic with steam shower, jacuzzi tub, and luxury bed and fireplace. Family Friendly OR Romantic Getaway!

The Peacock Place w/ Shared Seasonal Outdoor Pool

This 3 bedroom, 1 bath, open concept lower unit of a duplex is located in Brewer's Hill. This unit has tons of natural light, original hard wood floors, pocket doors and claw foot soaking tub. This pet friendly unit has off street parking for 2 vehicles or motorcycles, and a private yard with patio and BBQ grill for your use. Walking distance to Brady Street, downtown and Fiserv Forum.