Holiday rentals with a pool in Racine

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.

Wisconsin Retreat Family Favorite Quality Stay

Experience tranquility in this family friendly spacious home just steps away from Lake Michigan and local parks. Tucked away in a peaceful neighborhood yet close to dining and shopping, it boasts a beautiful fenced backyard with a 10 foot deep pool and cedar soaking hot tub(closed for season). Inside, indulge in the fully stocked coffee and espresso bar for the ultimate relaxation and smart tv's for your entertainment needs. Pool and hot tub are closed for the season. Parties are not allowed.

Unplug - Boat, pool, hot tub on Lake Michigan!

Have you stayed in a boat allowing the sun to wake you up? Have you experienced the joy of doing nothing? In the lazy waves of Lake Michigan lies UNPLUG where we encourage you to practice the joy of doing nothing. Unplug has one large bed on board that can sleep 2 (Q size), a smaller Full bed, a small sofa, and a kitchen on board with basic amenities. The bathroom on board is not usuable but guests can use the clean well kept marina bathrooms and showers just a short walk away. Come unplug!

Close to Lake with Great Ammenities & Breakfast!

I want you to be able to do things here that you can't do in a hotel. If you're grillilng out, having a bonfire or watching movies all night long, you can turn up that volumn as loud as you want all night long! I posted my listing under "entire home" as you do get so much more than just renting "a room". When I have guests I stay in my office or bedroom so my guests feel more comfortable utalizing entire home & yard. In fact, if you don't ask for breakfast, you may not even see me at all.

3 Bedrooms, 2.5 bath, 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!

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.

"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.

Wooded Hills/Indoor Pool/Hot Tub/Arcade

Discover the allure of our 5BR Wisconsin retreat, where spacious elegance meets comfort. Enjoy a gourmet kitchen, a grand living room, and a game room with free arcade play. Dive into relaxation with our private, heated indoor pool. Outdoors, the terraced patio and fire pit invite memorable moments. Minutes from Milwaukee, our home is an idyllic base for both peaceful relaxation and lively exploration. Perfect for family or corporate escapes, it's a stay you'll cherish.

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!

LG Quaint Condo on Lakeshore Dr.

Charming 1+1 condo off Lakeshore Blvd, just minutes from downtown Lake Geneva. A perfect blend of quaint and modern, with a full coffee and tea station and a fully equipped kitchen. Stroll to the lake, take a boat ride, or enjoy a scenic drive to downtown. Experience the peaceful charm of Lake Geneva with the convenience of being close to all its attractions. Book this condo alone or with another in the same building for extra space.

Brewers Hill Gem w/hot tub & seasonal shared pool

Your family will be close to everything when you stay at this centrally-located place. Walking distance to Brady Street, the Milwaukee River Walk, shops, restaurants and coffee houses. Less than a mile from Fiserv Forum, downtown Milwaukee and just minutes from Bradford Beach. This pet friendly unit has a private fenced in yard, BBQ grill, off street parking for your vehicles and motorcycles, and a hot tub for your use.

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!