Pine Ridge Vacation Packages
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Your Pine Ridge Vacation
Lock in a Pine Ridge vacation package and prepare to experience the best of this city. Consider basing yourself in the neighborhood of Pelican Bay, which is great for coastal beaches, shopping and dining. Ready to start exploring your surroundings? Barefoot Beach, Naples Zoo at Caribbean Gardens and Vanderbilt Beach are some of the leading places to visit during your trip to Pine Ridge. A couple of quick clicks is all it takes to build a tailored Pine Ridge vacation on Expedia.
Top Pine Ridge Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Casa Ybel Resort
Mid Island
CA $824
per person
Sep 14 - Sep 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Myers (RSW)
8.8/10 Excellent! (397 reviews)
First time at CY and could not be happier with our stay. First time on the island too. Room was perfect for me and my two daughters. Really liked the vaulted ceilings as I was surprised by this. We stayed on the 2nd floor for the view (we didn’t mind walking the extra steps). We were in room 118 and it was a little walk to the pool, but the grounds are gorgeous as we didn’t mind the walk. Pool was big and water warm! Ocean was equally as warm. Shells for days. Caught some lizards and a crab! Staff was excellent and courteous. Come prepared with bug spray. We used Captiva Cruises for our private fishing, snorkeling, shelling, and dolphin viewing. Caught tons of fish! Grilled snapper and trout for dinner. We will be returning annually!
Reviewed on Aug 10, 2026
The Perry Hotel Naples
CA $1,318
per person
Oct 29 - Nov 4
found 23 hours ago
Roundtrip flight included
Detroit (DTW) to Fort Myers (RSW)
9.6/10 Exceptional! (992 reviews)
We had a great time at the Perry Hotel - the staff were all so kind & helpful, property is beautiful & the boat shuttle to the beach is a hidden gem!
Reviewed on Aug 11, 2026
Manasota Key Resort
CA $1,463
per person
Sep 25 - Oct 1
just found
Roundtrip non-stop flight included
Toronto (YYZ) to Fort Myers (RSW)
9.4/10 Exceptional! (304 reviews)
Wow! I wasn’t sure what to expect with this being our 1st trip to this part of FL! But it exceeded our expectations! The view of the ocean, clean room, amenities, and ease of laundry! Helpful staff and so welcoming! We will for sure be back! Thank you!
Reviewed on Aug 10, 2026
Tween Waters Island Resort & Spa
CA $1,705
per person
Nov 1 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Myers (RSW)
8.6/10 Excellent! (1,005 reviews)
Very nice place to enjoy and have a good time. Beach across the street, pool bar and restaurants nearby. Super quite and relaxing. We definitely recommend this place and hopefully coming back soon
Reviewed on Aug 10, 2026
Ready to book your vacation to Pine Ridge?
Pine Ridge Hotel Deals
Margaritaville Beach Resort Fort Myers
251 Crescent Street Fort Myers Beach FL
Fully refundableReserve now, pay when you stay
CA $241
CA $339 total
Aug 31 - Sep 1
includes taxes & fees
Hyatt House Naples/5th Avenue
1345 5th Avenue South Naples FL
Fully refundableReserve now, pay when you stay
CA $201
CA $223 total
Sep 8 - Sep 9
includes taxes & fees
9/10 Wonderful! (2,011 reviews)
"Excelente"
Reviewed on Aug 11, 2026
Lani Kai Beachfront Resort
1400 Estero Blvd Fort Myers Beach FL
Fully refundableReserve now, pay when you stay
CA $170
CA $221 total
Aug 12 - Aug 13
includes taxes & fees
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.
What to do in Pine Ridge
Gulf of Mexico Sunset Cruise from Naples
CA $93
per adult
88% of travellers recommend
Frequently asked questions
How much does a Pine Ridge vacation package cost?
You'll find cheap prices from CA $824 on Expedia for your Pine Ridge escape. However, a range of factors like the length of stay, the season and your choice of hotel will determine how much your vacation to Pine Ridge costs.
What are the cheapest months to go to Pine Ridge?
Plan your getaway for the low or shoulder season and you're likely to score cheap Pine Ridge vacation packages. Keep in mind that school vacation periods and major festivals and events can impact prices, so do your research before booking.
How many days is enough for Pine Ridge?
To fully enjoy a Pine Ridge vacation, we suggest booking for 5 days. Split your time between discovering Delnor-Wiggins Pass State Park, Clam Pass Park and other leading sights, in addition to experiencing neighbourhoods like Park Shore and Moorings. If you've got some spare time, add a day trip to your Pine Ridge vacation itinerary.
How to find the best Pine Ridge package deals?
Landing a cheap Pine Ridge package deal is a breeze with Expedia. After you've entered your destination and preferred dates under our "Packages" tab, set your budget, add some filters and see what's available. You can tweak your search by "Amenities," "Property type," "Popular locations" and more. Order the results by "Price: low to high" to view the most pocket-friendly Pine Ridge package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are typically lower.
Is it cheaper to book a Pine Ridge vacation as a package?
You can enjoy significant savings on your Pine Ridge escape by booking a personalized vacation package. Click on the "Package" heading, then enter your travel dates and destination to browse the best hotel prices and airfares. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Pine Ridge?
If you're considering a spontaneous Pine Ridge getaway, check out our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can score terrific deals on your hotels and flights by booking well in advance.
How to plan a trip to Pine Ridge?
- Pick your dates: The things you plan to do in Pine Ridge and your preferred season will help you decide when to travel.
- Budget wisely: Besides the cost of your stay, you should consider other expenses too. These include food, transportation and flights. Also, set aside a little extra for unexpected expenses that could arise during your trip to Pine Ridge.
- Work out your trip length: Think about how long you'd like to spend discovering Pine Ridge. Plan your itinerary so you can get to all the experiences and attractions you're interested in at a comfortable pace.
- Bundle your accommodations and airfare: Once you've settled on your dates and duration, lock in the perfect Pine Ridge vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
