Explore South Side Golf Retreats
About South Side Vacation Rentals
Explore over 571 golf accommodation rentals in South Side. From luxurious golf villas to cozy golf cabins, golf resorts, and exclusive golf hotels, each offers premium amenities designed for families, groups, and golf enthusiasts. Enjoy exceptional comfort and a one-of-a-kind golf experience with these incredible accommodations. Perfect for tranquil golf escapes, relaxing retreats, or golf-inspired getaways, these properties provide style and comfort in South Side.
Looking for last-minute deals or the best offers on golf villas, golf cabins, golf resorts, and other golf retreats? StayAndPlay makes it easy to compare options in South Side. Choose from spacious family-friendly stays, charming golf escapes, or luxurious golf retreats tailored for ultimate relaxation and play.
Find spacious family-friendly golf accommodations, golf cottage, or luxurious golf villas—all designed for maximum comfort and convenience during your visit.On average, golf accommodation rentals in South Side offer approximately 854.64 ft² of space, giving you and your group plenty of room to relax and enjoy the stunning golf course surroundings.
The average nightly rate for golf accommodation rentals in South Side typically ranges around US $505.
StayAndPlay offers a secure and convenient platform to compare and book the best golf retreats in South Side. Explore a wide range of properties at unbeatable rates, and enjoy a unique stay immersed in golf with us.
Top Golf Accommodation Types in South Side
| Type | Count |
|---|---|
| Holiday Apartments | 472 |
| Vacation Homes | 20 |
Use these Quick Filters to Find a Vacation Rental in South Side
★ Pro Tip: StayAndPlay simplifies your search for the best golf accommodations from leading vacation rental OTAs like Booking.com and more. Use our Advanced Filter to explore golf villas, cozy golf cabins, golf hotels, and golf resorts. Filter by availability, pricing, cancellation options, and amenities to discover the ideal golf retreat in South Side.
Weather in South Side, IL
View the weather forecast for South Side before booking your South Side Vacation Rentals to confirm your best time to go.
Activities South Side Guest Reviews Local Attractions
StayAndPlay offers a diverse selection of the top golf villas, golf hotels, and other golf retreats around the world. South Side Guest Reviews Find the Best Golf Experiences & Activities for Your Golf Trip
Find Nearby Cabin Rentals in these Cities & Neighborhoods
Frequently Asked Questions About South Side?
What are the best golf resorts, luxury villas, and vacation rentals in South Side?
Looking for a place to stay in South Side? Explore these highly-rated golf vacation rentals for a one-of-a-kind golf retreat, where you can relax, unwind, and get ready to play your best game:
- Hyatt Regency McCormick Place Chicago
- South Loop 3 Bedroom Apt
- South Loop 3 Bedroom Apt
- South Loop 2 Bedroom Apt
- South Loop 2 Bedroom Apt
- Hyatt Regency McCormick Place Chicago
- Best Western Grant Park Hotel
- Homewood Suites By Hilton Chicago Downtown South Loop
- Sweet South Loop 1BR w/Indoor Pool, Golf Sim, nr Museums, by Blueground
- 1 #33 - 4 Bedroom/2 Bath Condo near McCormick Place, Wintrust Arena, Chinatown
How many golf stays with private pools are available in South Side?
Find exceptional golf retreats with private pools near South Side on StayAndPlay. Relax in serene golf vacation rentals with exclusive pool access and picturesque golf course views. Whether it's a spacious golf villa or a secluded golf cabin, these properties offer the perfect blend of luxury and relaxation, so you can focus on your game.
- S Loop Studio w Pool Gym Spa nr Grant Park CHI-739
- S Loop 2BR w Pool Gym Spa nr Grant Park CHI-740
- S Loop 1BR w Pool Gym nr Soldier Field CHI-350
What are the top-rated golf retreats in South Side for family stays?
Searching for a family-friendly golf retreat in South Side? Explore these top-rated options, each loved by families and groups who have stayed in South Side:
- Spacious 4BR Suite Near McCormick & Soldier Field
- Walkable 2BR Apartment in Chicago South Loop with Optional Parking and Gym Access Near McCormick Place, Museum Campus & Lakefront
- Marriott Marquis Chicago
How many StayAndPlay golf vacation rentals are available in South Side?
StayAndPlay, as of 2026, features over 571 unique golf villas, golf hotels, golf resorts, and more in South Side. Choose from eco-friendly golf accommodations, golf hotels and golf resorts, with new options added frequently.
By 2026, StayAndPlay has curated over 571 stunning properties in South Side, sourced from trusted platforms. Plan your next golf trip now.
For 2026, StayAndPlay provides access to over 571 premier golf accommodations in South Side. Find your ideal golf-retreat and play your best game with StayAndPlay.
Nearby Neighborhood (11)
| Neighborhood | Property Count |
|---|---|
| Downtown Chicago Golf Rental Cottages and Golf Getaways in Chicago, Illinois | 1501 |
| The Loop Golf Rental Cottages and Golf Getaways in Chicago, Illinois | 672 |
| South Loop Golf Rental Cottages and Golf Getaways in Chicago, Illinois | 384 |
| Near South Side Golf Rental Cottages and Golf Getaways in Chicago, Illinois | 369 |
| Near West Side Golf Rental Cottages and Golf Getaways in Chicago, Illinois | 323 |
| Prairie District Golf Rental Cottages and Golf Getaways in Chicago, Illinois | 272 |
| West Loop Golf Rental Cottages and Golf Getaways in Chicago, Illinois | 184 |
| Lower West Side Golf Rental Cottages and Golf Getaways in Chicago, Illinois | 57 |
| Printers Row Golf Rental Cottages and Golf Getaways in Chicago, Illinois | 3937 |
| Chinatown Golf Rental Cottages and Golf Getaways in Chicago, Illinois | 2998 |
| Chicago Museum Campus Golf Rental Cottages and Golf Getaways in Chicago, Illinois | 3119 |
