Search Deals onO Brien Vacation Packages
O Brien Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
La Quinta Inn & Suites by Wyndham Ocala
Price was $477, price is now $382 per person
$382
per person
Nov 7 - Nov 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Gainesville (GNV)
Book a stay at this business-friendly hotel in Ocala. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions World Equestrian Center – Ocala and Paddock Mall are located nearby.
Landing Apartments Northwest Ocala
Price was $1,437, price is now $1,084 per person
$1,084
per person
Nov 26 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Gainesville (GNV)
Stay at this apartment in Ocala. Enjoy free parking, a 24-hour fitness center, and a conference center. Popular attractions World Equestrian Center – Ocala and I-75 Super Flea Market are located nearby.
Equus Inn Ocala
Price was $566, price is now $428 per person
$428
per person
Nov 7 - Nov 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Gainesville (GNV)
Book a stay at this business-friendly hotel in Ocala. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions World Equestrian Center – Ocala and Paddock Mall are located nearby.
Baymont by Wyndham Ocala Suites
Price was $542, price is now $447 per person
$447
per person
Nov 7 - Nov 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Gainesville (GNV)
Book a stay at this business-friendly motel in Ocala. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Silver Springs State Park and Marion County Museum of History and Archaeology are located nearby.
La habitacion y el baño estaban limpios, la cama comoda.
El desayuno tenia huevo duro, yogurts, bagels, cereales, wafles, estaba bien. El ambiente del desayuno muy limpio.
La ubicacion, centrica. A menos de 10 minutos de Silver Springs.
Reviewed on Sep 21, 2026
Hilton Ocala
Price was $1,064, price is now $885 per person
$885
per person
Nov 26 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Gainesville (GNV)
Book a stay at this business-friendly hotel in Ocala. Enjoy breakfast (surcharge), a 24-hour fitness center, and parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Ocala Downtown Square and World Equestrian Center – Ocala are located nearby.
The Equestrian Hotel
Price was $1,828, price is now $1,526 per person
$1,526
per person
Nov 26 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Gainesville (GNV)
Book a stay at this luxury resort in Ocala. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions World Equestrian Center – Ocala and Golden Ocala Golf Course are located nearby.
Shire Village
Price was $1,821, price is now $1,525 per person
$1,525
per person
Nov 26 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Gainesville (GNV)
Stay at this apartment in Ocala. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Sholom Park and Florida Aquatics Swimming and Training are located nearby.
The Riding Academy Hotel
Price was $1,478, price is now $1,243 per person
$1,243
per person
Nov 26 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Gainesville (GNV)
Book a stay at this spa hotel in Ocala. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions World Equestrian Center – Ocala and Golden Ocala Golf Course are located nearby.
O Brien Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
O Brien Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Tue, Oct 27 - Sat, Oct 31
BWI
Baltimore Washington Intl. Thurgood Marshall
JAX
Jacksonville Intl.
$119 Roundtrip, found 1 day ago
$119
Roundtrip
found 1 day ago
Tue, Nov 3 - Tue, Nov 10
PHL
Philadelphia Intl.
JAX
Jacksonville Intl.
$137 Roundtrip, found 2 hours ago
$137
Roundtrip
found 2 hours ago
Tue, Nov 10 - Thu, Nov 19
ORD
O'Hare Intl.
JAX
Jacksonville Intl.
$189 Roundtrip, just found
$189
Roundtrip
just found
Mon, Nov 2 - Thu, Nov 5
AUS
Austin-Bergstrom Intl.
JAX
Jacksonville Intl.
$204 Roundtrip, found 2 days ago
$204
Roundtrip
found 2 days ago
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