Chicago\92s Best Vacation Rentals - Vacation Rentals in Greater Woodlawn

The Kenwood Gables Boutique Bed & Breakfast From US $247
         

Luxury Places to Stay in Greater Woodlawn

Over 1624+ Luxury Places to Stay in or Near Greater Woodlawn
The Most Luxurious home on the market From US $2,087
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Exquisite View From US $1,181
         

9.8 (6 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Top-Rated Vacation Rentals with a Pool in Greater Woodlawn

Over 317+ Top-Rated Vacation Rentals with a Pool in or Near Greater Woodlawn
Chic 2BR Getaway Walk to Breweries and Art Walk From US $261
         

|
10.0 (7 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
City Vibes 2BR Walk Everywhere in DWNTN St. Pete From US $302
         

|
10.0 (4 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Tropicana Stadium 2 Bed In DWTWN With Free Parking From US $585
         

|
10.0 (3 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly

Pet-Friendly Vacation Rentals in Greater Woodlawn

Over 683+ Pet-Friendly Vacation Rentals in or Near Greater Woodlawn
Updated St Petersburg Apt - Downtown Location From US $320
         

Large Vacation Homes & Villas in Greater Woodlawn

Over 71+ Large Vacation Homes & Villas in or Near Greater Woodlawn
Coastal Cottage From US $88
         

|
10.0 (65 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Balcony/Terrace
Chic 3 Bedroom 3 Bathroom Grand Central Bungalow From US $421
         

Wheelchair Accessible Vacation Homes in Greater Woodlawn

Over 172+ Wheelchair Accessible Vacation Homes in or Near Greater Woodlawn
Sun & Culture | St. Pete 2BR Next to the Action From US $347
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Hollander Boutique Hotel From US $259
         

Modern 2 Bed Getaway Steps from Tropicana Field! From US $328
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Experience St. Pete: Charming 1-Bed by Tropicana From US $381
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Experience St. Pete: Charming 1-Bed by Tropicana Field From US $283
         

City Vibes 2BR | Walk Everywhere in DWNTN St. Pete From US $302
         

Chic 2BR Getaway Walk to Breweries & Art Walk From US $442
         

8.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly

Greater Woodlawn Varoom and Airbnb Places to Stay Under $200

Over 957+ Greater Woodlawn Varoom and Airbnb Places to Stay Under $200
The Inn on Third From US $135
         

9.6 (1001 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Experience the Best of Downtown St. Pete! From US $188
         

Instantly Bookable Vacation Homes in Greater Woodlawn

Over 899+ Instantly Bookable Vacation Homes in or Near Greater Woodlawn
Uptown Bungalow 2/2 From US $220
         

10.0 (5 Reviews)
House
  • Air Conditioner
  • Balcony/Terrace
  • Security/Safety

About Greater Woodlawn Vacation Rentals

With more than 1633 Greater Woodlawn 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 Greater Woodlawn.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Chicagosbestvacationrentals Greater Woodlawn, 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 Greater Woodlawn. Places to stay near Greater Woodlawn are 553.28 ft² on average, with prices averaging $234 a night.

Chicagosbestvacationrentals makes it easy and safe to find and compare vacation rentals in Greater Woodlawn 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 Greater Woodlawn

Type Count
Vacation Homes 735
Holiday Apartments 684
Hotels with Suites 68
B&B 44
Cottages 35
Villas 3
Cabin Rentals 2
Resorts 2
Ski Chalet Rentals 1

Use these Quick Filters to Find a Vacation Rental in Greater Woodlawn

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 Greater Woodlawn.

Weather in Greater Woodlawn

View the weather forecast for Greater Woodlawn before booking your Greater Woodlawn 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