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O Brien Vacation Packages

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O Brien Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Nature Coast Inn and Cottages

Nature Coast Inn and Cottages

3 out of 5
Price was $498, price is now $426 per person
$426
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Gainesville (GNV)
Stay at this cottage in Inglis. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Yankeetown Library and Yankeetown Water Resources Park are located nearby.

Landing Apartments Northwest Ocala

Landing Apartments Northwest Ocala

3 out of 5
Price was $1,327, price is now $996 per person
$996
per person
Nov 6 - Nov 13
found 21 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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.
The place itself is beautiful. The property has so many amenities which make it so enjoyable such as mini golf, the pool and the gym all of which is clean and new. Our apartment was amazing, super spacious, quiet, clean and overall amazing. The host was super friendly and communicated with us throughout our stay when needed. 10/10 I would love to come back!

Reviewed on Jun 23, 2026

Equus Inn Ocala

Equus Inn Ocala

2.5 out of 5
Price was $960, price is now $740 per person
$740
per person
Nov 6 - Nov 13
found 24 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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.

Landing Apartments Newberry

Landing Apartments Newberry

4 out of 5
Price was $1,288, price is now $1,012 per person
$1,012
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Gainesville (GNV)
Stay at this aparthotel in Newberry. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Jonesville Tennis Center and Dudley Farm Historic State Park are located nearby.
The apartment was clean. The area was quiet. It had great amenities

Reviewed on Jul 28, 2026

The Equestrian Hotel

The Equestrian Hotel

5 out of 5
Price was $1,659, price is now $1,306 per person
$1,306
per person
Oct 1 - Oct 8
found 23 hours ago
Roundtrip non-stop flight included
New York (JFK) 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.
What a BEAUTIFUL hotel and property! All of the staff are friendly , welcoming and helpful! If you ever have to be in the area you must book a stay!

Reviewed on Aug 23, 2026

The Riding Academy Hotel

The Riding Academy Hotel

2.5 out of 5
Price was $1,272, price is now $1,038 per person
$1,038
per person
Oct 1 - Oct 8
found 23 hours ago
Roundtrip non-stop flight included
New York (JFK) 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.
The property is lovely and well maintained. The staff is friendly. The restaurants are fair.

Reviewed on Aug 25, 2026

Holiday Motel Ocala Downtown I-75

Holiday Motel Ocala Downtown I-75

2.5 out of 5
Price was $582, price is now $523 per person
$523
per person
Nov 12 - Nov 15
found 3 hours ago
Roundtrip non-stop flight included
New York (LGA) to Gainesville (GNV)
Stay at this hotel in Ocala. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Silver Springs State Park and Ocala Downtown Square are located nearby.

Shire Village

Shire Village

3.5 out of 5
Price was $987, price is now $901 per person
$901
per person
Nov 12 - Nov 15
found 3 hours ago
Roundtrip non-stop flight included
New York (LGA) 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.

O Brien Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Nature Coast Inn and Cottages

Nature Coast Inn and Cottages

3 out of 5
Price was $498, price is now $426 per person
$426
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Gainesville (GNV)
The Equestrian Hotel

The Equestrian Hotel

5 out of 5
Price was $1,167, price is now $974 per person
$974
per person
Nov 12 - Nov 15
found 3 hours ago
Roundtrip non-stop flight included
New York (LGA) to Gainesville (GNV)
Equus Inn Ocala

Equus Inn Ocala

2.5 out of 5
Price was $657, price is now $565 per person
$565
per person
Nov 12 - Nov 15
found 3 hours ago
Roundtrip non-stop flight included
New York (LGA) to Gainesville (GNV)
Landing Apartments Northwest Ocala

Landing Apartments Northwest Ocala

3 out of 5
Price was $887, price is now $764 per person
$764
per person
Nov 12 - Nov 15
found 3 hours ago
Roundtrip non-stop flight included
New York (LGA) to Gainesville (GNV)

O Brien Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Equus Inn Ocala

Equus Inn Ocala

2.5 out of 5
Price was $960, price is now $740 per person
$740
per person
Nov 6 - Nov 13
found 24 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Gainesville (GNV)
Landing Apartments Northwest Ocala

Landing Apartments Northwest Ocala

3 out of 5
Price was $1,327, price is now $996 per person
$996
per person
Nov 6 - Nov 13
found 21 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Gainesville (GNV)
Landing Apartments Newberry

Landing Apartments Newberry

4 out of 5
Price was $1,288, price is now $1,012 per person
$1,012
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Gainesville (GNV)
The Equestrian Hotel

The Equestrian Hotel

5 out of 5
Price was $1,659, price is now $1,306 per person
$1,306
per person
Oct 1 - Oct 8
found 23 hours ago
Roundtrip non-stop flight included
New York (JFK) to Gainesville (GNV)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Frontier Airlines
Tue, Nov 10 - Thu, Nov 12
ORD
O'Hare Intl.
JAX
Jacksonville Intl.
$193 Roundtrip, found 4 hours ago
$193
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Tue, Nov 10 from O'Hare Intl. to Jacksonville Intl., returning Thu, Nov 12, priced at $193 found 4 hours ago
Bargain Flight
Sun, Jan 17 - Sat, Jan 30
DCA
Ronald Reagan Washington National
JAX
Jacksonville Intl.
$213 Roundtrip, found 3 days ago
$213
Roundtrip
found 3 days ago
Select Bargain Flight flight, departing Sun, Jan 17 from Ronald Reagan Washington National to Jacksonville Intl., returning Sat, Jan 30, priced at $213 found 3 days ago
Frontier Airlines
Tue, Oct 27 - Sat, Oct 31
BWI
Baltimore Washington Intl. Thurgood Marshall
JAX
Jacksonville Intl.
$220 Roundtrip, found 2 days ago
$220
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Tue, Oct 27 from Baltimore Washington Intl. Thurgood Marshall to Jacksonville Intl., returning Sat, Oct 31, priced at $220 found 2 days ago
Bargain Flight
Tue, Nov 3 - Thu, Nov 5
DFW
Dallas-Fort Worth Intl.
JAX
Jacksonville Intl.
$243 Roundtrip, found 1 day ago
$243
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Tue, Nov 3 from Dallas-Fort Worth Intl. to Jacksonville Intl., returning Thu, Nov 5, priced at $243 found 1 day ago