Pine Ridge Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

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

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.
Tween Waters Island Resort & Spa

Tween Waters Island Resort & Spa

3 out of 5
Price was CA $1,251, price is now CA $830 per person
CA $830
per person
Sep 13 - Sep 16
found 6 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Myers (RSW)
8.6/10 Excellent! (1,004 reviews)
We love staying at Tween Waters on Captiva Island! We have stayed here several times. Our room was clean, the bed was comfortable and we enjoyed the view of the bay from our room! We met friends here and we all had fun over the 4th of July. It is so nice to enjoy the pool, the beach and restaurants at Tween Waters but what we love the most is being able to go boating while we are there. We usually bring our own boat but this time our friends brought their boats. It is nice to be able to enjoy boating and using the boat docks along with all the great amenities that Tween Waters offers!

Reviewed on Jul 7, 2026

GullWing Beach Resort

GullWing Beach Resort

3.5 out of 5
South Island
Price was CA $1,718, price is now CA $1,162 per person
CA $1,162
per person
Sep 8 - Sep 15
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
9.4/10 Exceptional! (955 reviews)
We have stayed here before. We love how big the rooms are. The pool is always clean. Their is always someone cleaning around the property

Reviewed on Jun 27, 2026

Sunsuites Villas At Sunseeker Resort, Curio By Hilton

Sunsuites Villas At Sunseeker Resort, Curio By Hilton

4 out of 5
Price was CA $1,855, price is now CA $1,306 per person
CA $1,306
per person
Aug 12 - Aug 19
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Fort Myers (RSW)
9.2/10 Wonderful! (30 reviews)
Expextacular

Reviewed on Jul 8, 2026

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 $2,043, price is now CA $1,443 per person
CA $1,443
per person
Aug 24 - Aug 28
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Fort Myers (RSW)
9/10 Wonderful! (1,009 reviews)
Todo espectacular la playa las piscinas la habitación el servicio todo muy especial

Reviewed on Jul 9, 2026

Inn on Fifth

Inn on Fifth

4 out of 5
Old Naples
Price was CA $1,626, price is now CA $1,182 per person
CA $1,182
per person
Aug 21 - Aug 25
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Fort Myers (RSW)
9.4/10 Exceptional! (1,001 reviews)
Great location! Overall, room was clean and there was no carpet (which is a plus for us). Pool is small but very enjoyable!

Reviewed on Jul 6, 2026

Ready to book your vacation to Pine Ridge?

 

Choose your dates

Pine Ridge Hotel Deals

Margaritaville Beach Resort Fort Myers

Margaritaville Beach Resort Fort Myers

4 out of 5
251 Crescent Street Fort Myers Beach FL
The price is CA $273 per night from Aug 4 to Aug 5
CA $273
CA $375 total
Aug 4 - Aug 5
includes taxes & fees
9/10 Wonderful! (2,313 reviews)
"Excellent place to get away and relax! Room was clean and spacious and very well decorated for relaxation! My only complaint would be that there were so many people using day passes for the pool that it became too crowded for our liking"

Reviewed on Jul 9, 2026

Margaritaville Beach Resort Fort Myers
Hyatt House Naples/5th Avenue

Hyatt House Naples/5th Avenue

3.5 out of 5
1345 5th Avenue South Naples FL
Fully refundableReserve now, pay when you stay
The price is CA $197 per night from Aug 9 to Aug 10
CA $197
CA $219 total
Aug 9 - Aug 10
includes taxes & fees
9/10 Wonderful! (1,867 reviews)
"Clean room awesome"

Reviewed on Jul 8, 2026

Hyatt House Naples/5th Avenue
Great Wolf Lodge Naples

Great Wolf Lodge Naples

3 out of 5
3900 City Gate Blvd N. Naples FL
The price is CA $248 per night from Jul 16 to Jul 17
CA $248
CA $275 total
Jul 16 - Jul 17
includes taxes & fees
9.4/10 Exceptional! (1,031 reviews)
"Ok"

Reviewed on Jul 9, 2026

Great Wolf Lodge Naples
See all 11,737 properties in Pine Ridge
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

What to do in Pine Ridge

Naples Sightseeing Boat Tour

Naples Sightseeing Boat Tour

CA $81
per adult
96% of travellers recommend
Naples Sightseeing Boat Tour
Gulf of Mexico Sunset Cruise from Naples

Gulf of Mexico Sunset Cruise from Naples

CA $94
per adult
88% of travellers recommend
Gulf of Mexico Sunset Cruise from Naples
Naples: Sightseeing and Dining Cruises

Naples: Sightseeing and Dining Cruises

CA $111
per adult
Naples: Sightseeing and Dining Cruises
See all activities in Pine Ridge

Frequently asked questions

How much does a Pine Ridge vacation package cost?
You'll find cheap prices from CA $830 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?

  1. Pick your dates: The things you plan to do in Pine Ridge and your preferred season will help you decide when to travel.
  2. 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.
  3. 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.
  4. Bundle your accommodations and airfare: Once you've settled on your dates and duration, lock in the perfect Pine Ridge vacation package for you.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.