Holiday rentals with a pool in Kane County

Haven Estates_: Cozy Barn, Hot Spa & heated Pool

Enjoy a peaceful countryside retreat at this charming Barndominium set on 6.5 private acres, accommodating up to 8 guests This spacious getaway features an 18' x 36' private pool with a hot spa and a solar-heated pool room for year-round relaxation. The Great Room offers open-concept living with comfortable seating, recreation space, and four sleeper sofas. The cozy bedroom includes a king-size bed, while the fully equipped chef’s kitchen boasts an oversized island & a stove with an air fryer.

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.

Cozy & Spacious Suite in Quiet Neighborhood

This 950 sq. ft. guest suite is in a quiet, upscale neighborhood, less than 1/2 mile from Bartlett Hills Golf Club and a mile from Metra Train Station. 50 min. train ride to downtown Chicago. 10 min. walk to downtown Bartlett. A private entrance makes check-in easy and convenient, while offering privacy during your stay. Full kitchen, accessible bathroom, WIFI, and cable provided. Washer/Dryer available upon request. Pool is for registered guests only. Owners on site to assist if needed.

Couples Getaway! Hot Tub, Lake, Fire Pit, Trails

Private entrance to a stunning master suite.A VERY unique property.Sliding suite door opens to screened in pool room. Hot tub all year overlooking my private lake. Pool closed Oct. 1st. Seating area & TV to watch while lounging & swimming. (2) Kayaks 4 you. Walking & bike trails. I am minutes from everything U want. Grill, have a fire in the fireplace&fire pit.Bring your fishing poles! Time 2 RELAX in privacy. When not traveling, I live in main part of home. You won’t see me. No extra guests.

Peaceful Private Coach-House in St. Charles

Enjoy our cozy and peaceful Coach-house , private entrance with everything you need for a wonderful stay. Newly renovated and updated throughout. Queen bed with mattress topper, studio area includes Smart TV, water station, Keurig coffee machine and quick-set lock. Even though you are less than a mile from downtown St. Charles and 4 miles to the Geneva train station you have a private area. You may see deer out your window overlooking the pool and tennis. Not suitable for children or pets.

Friends-Inspired Vintage Vibes House near Chicago

Welcome to Your “Friends in Chicago” Getaway! Step inside and be transported into the iconic vibes of the Friends TV show. Our cozy Schaumburg home features a Friends-inspired living room — the perfect spot for gathering, snapping photos, and enjoying the nostalgia of your favorite sitcom. Friends-Style Living Room – Bright, cozy, and full of character. It’s your own Central Perk–style hangout. Spacious Comfort – 3 bedrooms and a roomy layout, perfect for families, groups, or friends .

Luxury Suburbs 2BR | Pickleball, Pool, Gym, Sauna

A designer, resort-like experience in a professionally managed 2 bedroom / 2 bathroom property, providing the perfect balance of luxury and comfort for business travelers and families. Enjoy the pool, pickleball court, kids play room, courtyard w/ firepits, fitness center, pool table, and sauna - convenience is at your fingertips! Explore nearby downtown Naperville (8 mins), classy Oakbrook Terrace, the beautiful Morton Arboretum and downtown Chicago, a short drive or train ride away!

Spacious 5bd/5bth house w/Pool, Hot Tub, Sauna

Luxury 5,000 Sq Ft Retreat in St. Charles Relax and recharge in this serene, castle-inspired home. Perfect for family getaways, it features 5 bedrooms, 5 bathrooms, and space for up to 15 guests. Amenities include: • Outdoor pool (summer, can be heated for additional charge) • Hot tub • Sauna & Tiki bar in the pool house • Massage chair in the master bedroom • Finished basement • Viking kitchen appliances • EV charger No parties or events allowed. Book your relaxing stay today!

Paradise with Pool & Games

Welcome to our home. Enjoy lazy summer days by our sparkling pool, where you can soak up the sun and cool off with refreshing dips. Our well-appointed kitchen is ideal for preparing delicious meals together, and the cozy living areas provide plenty of space for relaxation and bonding. With nearby attractions and easy access to downtown Chicago, our home offers the perfect balance of suburban serenity and urban excitement. We can't wait to host you for an unforgettable stay!

"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.

30 mins to CHI, 3 Kings, BBQ Grill, TV, Spacious

Discover the Farmhouse on Main! Where character meets comfort. Soak up the sun by the in-ground pool with loungers, or enjoy a firepit for cozy nights. Fire up the BBQ grill or sip drinks at the granite bar. Inside, relax in the cozy seating areas, gather around the large dining table, and enjoy the spacious, fully equipped kitchen. ★ 5 minutes to downtown Plainfield ★ 20 minute drive to Naperville ★ Just a 30 minute drive into Chicago Come enjoy Plainfield with us!

Family-Friendly Suburban Getaway Near Chicago

Welcome to our spacious 4-bedroom home! Enjoy lounging in the airy living area or cooking in the fully equipped kitchen. With a master bedroom featuring a king bed and en-suite, a second bedroom with a king bed, a third with a queen, and an office space for the fourth bedroom, plenty of room. Plus, unwind with a game of pool on the basement's pool table. High-speed internet keeps you connected. Hot Tub open! Swimming Pool will be closed starting on October 1st.