Oak Hollow Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Top Holiday Package Deals in Oak Hollow

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Ft Myers

Hilton Garden Inn Ft Myers

3 out of 5
Villas
Price was CA $643, price is now CA $399 per person
CA $399
per person
Nov 21 - Nov 24
found 6 hours ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
8.6/10 Excellent! (1,009 reviews)
Over all a good stay and great price. Only issue would be the mattress was old lumpy , came home with back pain.

Reviewed on Sep 8, 2025

LaPlaya Beach & Golf Resort - A Noble House Resort

LaPlaya Beach & Golf Resort - A Noble House Resort

4.5 out of 5
Vanderbilt Beach
Price was CA $4,656, price is now CA $2,044 per person
CA $2,044
per person
Nov 29 - Dec 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
8.8/10 Excellent! (1,009 reviews)
Staff was friendly, hotel had a lot of construction outside by pool and beach, wasn't told this when I specifically called before I booked it. Also, Expedia shows prices that says inclusive of fees and taxes, yet I was charged $55 per day for "resort fee" plus additional minimal state and occupancy fees.

Reviewed on Sep 9, 2025

Inn on Fifth

Inn on Fifth

4 out of 5
Old Naples
Price was CA $2,257, price is now CA $1,182 per person
CA $1,182
per person
Oct 17 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Fort Myers (RSW)
9.4/10 Exceptional! (1,004 reviews)
They know how to make you feel special. The service was incredible; everyone is very, very friendly. The hotel is beautiful, very quiet, and centrally located just a few minutes from the beach. If you want a place to relax, this is the one. We will definitely be back.

Reviewed on Sep 8, 2025

The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Price was CA $1,049, price is now CA $587 per person
CA $587
per person
Oct 23 - Oct 27
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
9.6/10 Exceptional! (406 reviews)
nice and very clean, comfortable room, quit at night around the pool feel good

Reviewed on Sep 8, 2025

The Residences at Siesta Key Beach by Hyatt Vacation Club

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 out of 5
Price was CA $3,119, price is now CA $1,762 per person
CA $1,762
per person
Oct 18 - Oct 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Sarasota (SRQ)
9.8/10 Exceptional! (285 reviews)
Beautiful apartment! Great city view on the balcony. Pool area was lovely.

Reviewed on Aug 27, 2025

Where to stay in Oak Hollow

Find the best Oak Hollow areas and neighborhoods for the activities you enjoy most. Learn more about Oak Hollow
Default Image

South Gulf Cove

Cape Haze Pioneer Trail Park is one noteworthy place to stop while you're exploring South Gulf Cove and the surrounding area.

Find hotels in South Gulf Cove

Oak Hollow Hotel Deals

Sunseeker Resort Charlotte Harbor

Sunseeker Resort Charlotte Harbor

4.5 out of 5
5500 Sunseeker Way, 785, Punta Gorda, FL
Fully refundableReserve now, pay when you stay
The price is CA $187 per night from Oct 2 to Oct 3
CA $187
CA $270 total
Oct 2 - Oct 3
includes taxes & fees
Sunseeker Resort Charlotte Harbor
Country Inn & Suites by Radisson, Port Charlotte, FL

Country Inn & Suites by Radisson, Port Charlotte, FL

2.5 out of 5
24244 Corporate Ct, Port Charlotte, FL
Fully refundable
The price is CA $98 per night from Sep 14 to Sep 15
CA $98
CA $110 total
Sep 14 - Sep 15
includes taxes & fees
Country Inn & Suites by Radisson, Port Charlotte, FL
Fairfield Inn & Suites by Marriott Venice

Fairfield Inn & Suites by Marriott Venice

2.5 out of 5
2935 Executive Dr, Venice, FL
Fully refundableReserve now, pay when you stay
The price is CA $159 per night from Sep 21 to Sep 22
CA $159
CA $179 total
Sep 21 - Sep 22
includes taxes & fees
Fairfield Inn & Suites by Marriott Venice
See all 4,856 properties in Oak Hollow
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does an Oak Hollow vacation package cost?
The cheapest Oak Hollow vacation package is CA $399, so your dream escape can become a reality — without burning a hole in your pocket. Combine flights, hotels, car rentals and more to custom build a package that suits your travel style.
How do I get a cheap travel package to Oak Hollow?
By bundling. Hotels, flights and rental cars — combine whatever you need into an Oak Hollow vacation package to save a pile of cash. Score even better deals when you add extras such as tours or experiences to your booking. But that's not the only good part. You have the freedom to customize your vacation your way. We offer over 550 airlines and 1,000,000 hotel options worldwide, so that everyone has a chance to travel and fulfill those vacation fantasies.
Where should I stay in Oak Hollow?
With lots to explore in Oak Hollow, we recommend you secure a room in a hotel near its attractions. Fawcett Memorial Hospital, Bayfront Health Port Charlotte and Lake Betty Park are some interesting ones to put on your must-see list.
How far in advance should I book my Oak Hollow vacation?
Your best bet is to book early. Air carriers typically release flights up to a year in advance, and this is a great opportunity to land some of the cheapest prices. Boss just told you to take all your vacation days next month? That's alright! Expedia are never short on fantastic bargains to send you off on the getaway of your dreams, at an affordable price.
What does an Expedia Oak Hollow travel package include?
Much of that depends on you. You can pick from a variety of Oak Hollow bundles, such as a rental car, flight and hotel. You can also book a flight with a hotel, or a flight and a rental car. Once you've made your booking, you can add the fun stuff like tours and activities. Whatever your Oak Hollow trip looks like, get set to save!
What should I know before booking an Oak Hollow travel package?
When you book your flights, hotels and car rentals together, you'll nab awesome discounts. Whether you're organizing a beach escape in a villa or want to stay in a comfortable hotel in the city, Expedia can help make it happen.
Can I choose my airline with an Oak Hollow Expedia vacation package?
Yes, and with more than 550 airlines to pick from worldwide, you're spoiled for choice. Look through the available options and find out which airline best suits your needs and budget.
If I'm not able to travel, can I cancel my Oak Hollow vacation package?
Yes you can, and we'll help you every step of the way. You may be able to change or cancel your Oak Hollow vacation package for free within 24 hours of booking. But you may incur a fee from your airline, hotel or car rental company if you booked more than 24 hours ago. If your circumstances suddenly change, have a look at our Customer Service Portal for more information.

Discover the most popular places to visit in Oak Hollow

Riverwood Golf and Country Club

Enjoy a round of golf in Port Charlotte at Riverwood Golf and Country Club. Amble around this relaxing area's waterfront and enjoy its top-notch restaurants.

Riverwood Golf and Country Club

Lake Betty Park

Lake Betty Park is just one of the places to see in Port Charlotte, so why not enjoy the other things to explore during your travels? Amble around this quaint area's waterfront and enjoy its lively bars.

Lake Betty Park

Ollie's Pond Park

Ollie's Pond Park is just one of the places to see in Port Charlotte, so why not enjoy the other things to explore during your travels? Stroll along the waterfront in this relaxing area, or check out its top-notch restaurants.

Ollie's Pond Park

Things to do

"The Oasis" Tiki Boat

Sunset Tiki Boat Cruise (BYOB)

CA $81
per adult
Sunset Tiki Boat Cruise (BYOB)
See all activities in Port Charlotte
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.