Chicago\92s Best Vacation Rentals - Vacation Rentals in Liberty Square

Studio Biscayne Blvd Miami From US $79
         

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8.7 (44 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • View
FIFA Perfect 21 KM | ArTease 3: Walk to Wynwood & Design District From US $206
         

Luxury Places to Stay in Liberty Square

Over 3864+ Luxury Places to Stay in or Near Liberty Square
World Cup 2026 Dream Villa 3 From US $22,611
         

New
Villa
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
Wynwood | the bonds of art house | 7br | sleeps 18 From US $11,512
         

New
House
  • Parking
  • Pet Friendly
  • Designated Smoking Area
Sunlit Stylish Sanctuary - Ultimate Miami Luxury From US $10,672
         

Top-Rated Vacation Rentals with a Pool in Liberty Square

Over 1136+ Top-Rated Vacation Rentals with a Pool in or Near Liberty Square
Boho Chic House-POOL & FIREPIT - 15 mins to South Beach From US $640
         

Stylish 1bdr residence at Hyde Midtown From US $177
         

10.0 (19 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Miami Midtown Luxury Apartment with Parking From US $234
         

10.0 (18 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Private Home w/Pool - Steps from The Design District From US $489
         

Luxurious 2bd/2ba Condo in Wynwood w/Pool & FREE Parking From US $435
         

10.0 (7 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly

Pet-Friendly Vacation Rentals in Liberty Square

Over 1305+ Pet-Friendly Vacation Rentals in or Near Liberty Square
Contemporary 2BR Apartment in Midtown-Wynwood From US $132
         

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6.7 (24 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Wynwood Retreat From US $239
         

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9.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Miami Guesthouse Entire Back Building, 6 minutes to Wynwood From US $121
         

9.4 (11 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Hot Tub Fire Pit Miami Cruise Port Design District From US $594
         

10.0 (19 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Private Oasis with Pool sleeps 12, Brand new ! From US $3,290
         

10.0 (15 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Cozy and modern 2/1 apt near Midtown Miami and South Beach From US $185
         

10.0 (12 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Modern villa in Design District ! From US $683
         

10.0 (8 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Modern 2/1 apt near Midtown Miami and South Beach From US $175
         

10.0 (8 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Liberty Square

Over 714+ Large Vacation Homes & Villas in or Near Liberty Square
GUCCI MANOR 8 Bedrooms & Hot Tub From US $2,500
         

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New
House
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  • Balcony/Terrace
Lux Villa for 10 Miami Design District with Pool! From US $2,237
         

10.0 (23 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Divine Home in Design District 5BR From US $1,482
         

10.0 (5 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Miami Chic Hideaway: Near Wynwood & Downtown - Yard, Grill, & Games From US $647
         

Amazing Property Comfortable for Larger groups From US $3,494
         

10.0 (4 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
5BR HotTub/PoolTable/MiniGolf/7 min to Wynwood From US $896
         

10.0 (4 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Casa Bella in Design District/Wynwood From US $859
         

10.0 (4 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool
Centrally located 5 bedroom house with parking From US $473
         

10.0 (4 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Wheelchair Accessible Vacation Homes in Liberty Square

Over 818+ Wheelchair Accessible Vacation Homes in or Near Liberty Square
MiMo Home Studio with Private Entrance & Key From US $90
         

6.7 (30 Reviews)
House
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Midblock Miami From US $512
         

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10.0 (2 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
2 Bedroom Suite w/Balcony, Pool | Edgewater Stay From US $308
         

10.0 (6 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Pool
Lava Wynwood Luxury Condo Free Parking Rooftop Pool From US $240
         

Wynwood Condo, Walk to Restaurants & Nightclubs! From US $420
         

One Bedroom Condo King Bed With City Views From US $309
         

10.0 (3 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Trendy 1 Bdrm Condo, Miami Design District From US $298
         

10.0 (3 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool

Liberty Square Vacation Rentals and Airbnb Places to Stay Under $200

Over 1212+ Liberty Square Vacation Rentals and Airbnb Places to Stay Under $200
Cute, cozy mother-in-law suite in the heart of Miami From US $62
         

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9.3 (16 Reviews)
House
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Private Room Near Wynwood Free Parking From US $103
         

10.0 (1 Review)
House
  • Parking
  • Designated Smoking Area
  • Balcony/Terrace
Cozy Studio w/parking & Wi-Fi near Design District From US $107
         

10.0 (5 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Lux 2 Bed Apartment Close to Everything From US $198
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
King Bed! 5 minutes from everything in Miami From US $179
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
MIMO5-3 | cozy corner of Miami's Modern District From US $166
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Stylish 1-Bedroom Private Suite - Miami From US $131
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

Instantly Bookable Vacation Homes in Liberty Square

Over 2257+ Instantly Bookable Vacation Homes in or Near Liberty Square
Private Oasis with Pool sleeps 12, Brand new ! From US $3,090
         

10.0 (13 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Wynwood Charm 3, Live the art.1 Free Gated Parking From US $346
         

10.0 (7 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Balcony/Terrace
The teeny tiny housenn From US $277
         

10.0 (7 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Designated Smoking Area
La Orquidia From US $384
         

10.0 (6 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
3-Bedroom Home With Heated Pool And Short Drive To The Beaches. From US $492
         

About Liberty Square Vacation Rentals

With more than 3873 Liberty Square vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Chicagosbestvacationrentals and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Liberty Square.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Chicagosbestvacationrentals Liberty Square, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Liberty Square. Places to stay near Liberty Square are 643.89 ft² on average, with prices averaging US $481 a night.

Chicagosbestvacationrentals makes it easy and safe to find and compare vacation rentals in Liberty Square with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Liberty Square

Type Count
Vacation Homes 1580
Holiday Apartments 1490
Villas 161
Hotels 75
Cottages 22
B&B 19
Hostels 19
Others 4
Resorts 3
Ski Chalet Rentals 3
Cabin Rentals 1

Use these Quick Filters to Find a Vacation Rental in Liberty Square

Pro Tip: Chicagosbestvacationrentals makes it easy to compare the best listings on Chicagosbestvacationrentals homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Chicagosbestvacationrentals homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Liberty Square.

Weather in Liberty Square

View the weather forecast for Liberty Square before booking your Liberty Square Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Liberty Square Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Liberty Square?
How many vacation rentals are available in Liberty Square?

Currently, the total number of properties listed in 2026 is over 3873 in the Liberty Square area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Liberty Square.