Baldwin Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Baldwin Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Seasons Florida Resort
$370
per person
Oct 26 - Oct 31
found 23 hours ago
Roundtrip flight included
Chicago (MDW) to Orlando (MCO)
Book a stay at this business-friendly hotel in Kissimmee. Enjoy free WiFi, free parking, and laundry facilities. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Old Town and Disney Springs™ are located nearby.
Bn normal
Reviewed on Aug 18, 2026
Palazzo Lakeside Hotel
$398
per person
Oct 26 - Oct 31
found 23 hours ago
Roundtrip flight included
Chicago (MDW) to Orlando (MCO)
Stay at this hotel in Kissimmee. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular attractions Old Town and Disney Springs™ are located nearby.
Great stay! Clean,quiet, and safe :)
Reviewed on Aug 18, 2026
Margaritaville Cottages Orlando by Vstays with H2O Waterpark
$909
per person
Oct 26 - Oct 31
found 23 hours ago
Roundtrip flight included
Chicago (MDW) to Orlando (MCO)
Stay at this hotel in Kissimmee. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Disney's Animal Kingdom® Theme Park and Disney's Hollywood Studios® are located nearby.
The Delaney Hotel
South Orange
$568
per person
Oct 26 - Oct 31
found 24 hours ago
Roundtrip flight included
Chicago (MDW) to Orlando (MCO)
Book a stay at this business-friendly hotel in Orlando. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the restaurant and the bar in our reviews. Popular attractions Kia Center and Florida Mall are located nearby.
Property was very clean, staff was very pleasant and helpful. If parking, come into the garage from Fernwood St. Otherwise you'll go around a couple of blocks as there is no drop off or street parking on Orange Ave. The hotel is a wonderful boutique place with an excellent location to Orlando Regional Medical Center and South Downtown. Easy access to I-4. Drinks and refreshments are located at the front desk.
Reviewed on Aug 18, 2026
Magic Village Yards, Trademark Collection by Wyndham
$736
per person
Oct 26 - Oct 31
found 23 hours ago
Roundtrip flight included
Chicago (MDW) to Orlando (MCO)
Book a stay at this business-friendly aparthotel in Kissimmee. Enjoy free WiFi, free parking, and room service. Our guests praise the property condition in our reviews. Popular attractions Disney's Animal Kingdom® Theme Park and ESPN Wide World of Sports Complex are located nearby.
Muy bueno
Reviewed on Aug 18, 2026
Reunion Resort & Golf Club
Reunion
$704
per person
Oct 26 - Oct 31
found 23 hours ago
Roundtrip flight included
Chicago (MDW) to Orlando (MCO)
Book a stay at this luxury aparthotel in Kissimmee. Enjoy 11 outdoor pools, 7 restaurants, and a golf course. Our guests praise the helpful staff in our reviews. Popular attractions ESPN Wide World of Sports Complex and Old Town are located nearby.
The rooms are clean. The amenities are excellent. The hospitality of the transports are great.
Reviewed on Aug 13, 2026
Top Hotel Deals
Hyatt Regency Jacksonville
225 E Coastline Dr Jacksonville FL
Book a stay at this business-friendly hotel in Jacksonville. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and ...
Marriott Jacksonville Downtown
245 Water St Jacksonville FL
Book a stay at this business-friendly hotel in Jacksonville. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff in ...
Apm Inn and Suite
510 Lane Ave S Jacksonville FL
Stay at this hotel in Jacksonville. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our ...
Comfort Inn & Suites Jacksonville - Orange Park Near Naval Air Station
8001 PARRAMORE ROAD Jacksonville FL
Book a stay at this business-friendly hotel in Jacksonville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
DoubleTree by Hilton Hotel Jacksonville Riverfront
1201 Riverplace Boulevard Jacksonville FL
Stay at this hotel in Jacksonville. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the pool and the helpful staff in our reviews. Popular ...
Southbank Hotel by Marriott Jacksonville Riverwalk
1515 Prudential Dr Jacksonville FL
Book a stay at this business-friendly hotel in Jacksonville. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and ...
Hilton Garden Inn Jacksonville Downtown Southbank
1201 Kings Avenue Jacksonville FL
Stay at this hotel in Jacksonville. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. Popular attractions ...
Homewood Suites by Hilton Jacksonville Downtown-Southbank
1201 Kings Avenue Jacksonville FL
Book a stay at this business-friendly hotel in Jacksonville. Enjoy free breakfast, free WiFi, and room service. Our guests praise the helpful staff in our reviews. ...
Hampton Inn Jacksonville-Downtown-I-95
1331 Prudential Dr Jacksonville FL
Stay at this hotel in Jacksonville. Enjoy free breakfast, free WiFi, and room service. Our guests praise the helpful staff in our reviews. Popular attractions ...
Woodspring Suites Jacksonville Orange Park
1539 Wells Rd Orange Park FL
Stay at this hotel in Orange Park. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff in our reviews. Popular attractions ...
Suburban Studios Orange Park - Jacksonville near Naval Air Station
335 Eldridge Avenue Orange Park FL
Stay at this hotel in Orange Park. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions bestbet Orange Park and Orange Park Mall are ...
Rodeway Inn Orange Park - Jacksonville near Naval Air Station
335 Eldridge Ave Orange Park FL
Stay at this hotel in Orange Park. Enjoy free parking, a 24-hour front desk, and laundry facilities. Popular attractions bestbet Orange Park and Orange Park ...
Stayable Jacksonville West
910 Suemac Road Jacksonville FL
Stay at this hotel in Jacksonville. Enjoy free WiFi, free parking, and cable/satellite TV service. Popular attractions Gateway Shopping Center and Jacksonville-Baldwin ...
Motel 6 Jacksonville, FL - Orange Park
6107 Youngerman Circle Jacksonville FL
Stay at this motel in Jacksonville. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions ...
Quality Inn Jacksonville - Orange Park near Naval Air Station
4580 Collins Road Jacksonville FL
Book a stay at this business-friendly hotel in Jacksonville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Wed, Sep 9 - Tue, Sep 15
ORD
O'Hare Intl.
MCO
Orlando Intl.
$108
Roundtrip
found 4 days ago
Tue, Sep 15 - Tue, Sep 22
LGA
LaGuardia
MCO
Orlando Intl.
$162
Roundtrip
found 5 days ago
Tue, Oct 6 - Tue, Oct 13
DTW
Detroit Metropolitan Wayne County
MCO
Orlando Intl.
$172
Roundtrip
found 1 day ago
Sun, Jan 31 - Sat, Feb 6
PSM
Portsmouth Intl.
MCO
Orlando Intl.
$172
Roundtrip
found 5 days ago
Wed, Oct 7 - Wed, Oct 14
MSP
Minneapolis - St. Paul Intl.
MCO
Orlando Intl.
$207
Roundtrip
found 2 days ago
Best points of interest in Jacksonville
- Jacksonville Naval Air Station Vacations
- Orange Park Mall Vacations
- Prime F. Osborn III Convention Center Vacations
- Edward Waters College Vacations
- Florida Theatre Vacations
- Jacksonville Center for the Performing Arts Vacations
- Jacksonville Equestrian Center Vacations
- bestbet Orange Park Vacations
- St. Vincent's Medical Center Vacations
- Gateway Town Center Vacations
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