Pine Ridge 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

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.
Innovation Hotel

Innovation Hotel

4 out of 5
Price was CA $987, price is now CA $609 per person
CA $609
per person
Oct 16 - Oct 19
found 22 hours ago
Roundtrip flight included
Detroit (DTW) to Fort Myers (RSW)
9.8/10 Exceptional! (505 reviews)
Ultra modern and clean. Friendly staff

Reviewed on Aug. 10, 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 $1,926, price is now CA $1,050 per person
CA $1,050
per person
Oct 30 - Nov 2
found 2 hours ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
8.8/10 Excellent! (1,007 reviews)
Just what we wanted beach and golf. Restaurant services could do better, food was overpriced.

Reviewed on Aug. 14, 2025

Edison Beach House

Edison Beach House

3.5 out of 5
Price was CA $1,041, price is now CA $664 per person
CA $664
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Fort Myers (RSW)
9.4/10 Exceptional! (1,448 reviews)
The location is excellent, the hotel is clean, with friendly staff, the suite has everything we need, markets are 10 minutes away. I will definitely be back.

Reviewed on Aug. 19, 2025

The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Price was CA $1,181, price is now CA $759 per person
CA $759
per person
Oct 30 - Nov 2
found 2 hours ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
9.6/10 Exceptional! (365 reviews)
We stayed there a few weeks ago for our 19th year wedding anniversary. The rooftop sunset was amazing, diner with that view, even better. The restaurant paid attention to our reservations being labeled as an anniversary and surprised us with a unexpected desert. The pool, the property, the staff all amazing. If it wasn't for a billing/check out issue ( that they eventually corrected) it would have been the best hotel experience we have had since our honeymoon. This is the 3rd time staying at a perry hotel (twice in key West) and we can not wait to come back!!!

Reviewed on Aug. 19, 2025

Inn on Fifth

Inn on Fifth

4 out of 5
Old Naples
Price was CA $1,234, price is now CA $798 per person
CA $798
per person
Oct 16 - Oct 19
found 22 hours ago
Roundtrip flight included
Detroit (DTW) to Fort Myers (RSW)
9.4/10 Exceptional! (1,004 reviews)
Hotel was fabulous. Modern look, clean a beautiful room. Staff was fantastic, friendly and helpful. Pool was great. The hotel is located right in the middle of things on 5th Avenue @Naples.

Reviewed on Aug. 4, 2025

Ready to book your vacation to Pine Ridge?

 

Choose your dates

Pine Ridge Hotel Deals

Naples Grande Beach Resort

Naples Grande Beach Resort

4.5 out of 5
475 Seagate Drive, Naples, FL
The price is CA $209 per night from Sep 7 to Sep 8
CA $209
CA $293 total
Sep 7 - Sep 8
includes taxes & fees
9/10 Wonderful! (1,716 reviews)
"Súper friendly staff and great amenities"

Reviewed on Aug. 17, 2025

Naples Grande Beach Resort
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 $175 per night from Sep 1 to Sep 2
CA $175
CA $195 total
Sep 1 - Sep 2
includes taxes & fees
8.8/10 Excellent! (1,402 reviews)
Good location
"Ventilation could use some matainance. It did some strange vents maybe had mold around them. Kitchen chairs very heavy to move without disturbing rooms below. Over all nice roomy place with good location ."

Reviewed on Aug. 15, 2025

Hyatt House Naples/5th Avenue
La Quinta Inn & Suites by Wyndham Naples Downtown

La Quinta Inn & Suites by Wyndham Naples Downtown

2.5 out of 5
1555 5th Ave S, Naples, FL
Fully refundableReserve now, pay when you stay
The price is CA $94 per night from Sep 1 to Sep 2
CA $94
CA $104 total
Sep 1 - Sep 2
includes taxes & fees
8.2/10 Very Good! (1,591 reviews)
"Very friendly and helpful staff"

Reviewed on Aug. 17, 2025

La Quinta Inn & Suites by Wyndham Naples Downtown
See all 11,192 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

Discover the most popular places to visit in Pine Ridge

Naples Beach

Naples Beach

4.5/5(102 reviews)

Why not spend a carefree afternoon at Naples Beach during your travels in Naples? Stroll along the seaside or visit the shops while you're in the area.

Naples Beach
5th Avenue Shopping District which includes markets, street scenes and a city

Fifth Avenue South

Enjoy many happy hours exploring the variety of shops, dining options and cultural attractions of this popular shopping district in Naples, Florida.

Fifth Avenue South
Naples Pier featuring landscape views and a beach as well as a large group of people

Naples Pier

4.5/5(74 reviews)

Visit this beloved Naples destination to experience the simple charms of the beachfront on a dock that has served the city for more than 100 years.

Naples Pier

What to do in Pine Ridge

SEAS The Day with Pure Florida

Naples Sightseeing Boat Tour

CA $88
per adult
98% of travellers recommend
Naples Sightseeing Boat Tour
Cute Manatee

Manatee Sightseeing and Wildlife Boat Tour

CA $96
per adult
90% of travellers recommend
Manatee Sightseeing and Wildlife Boat Tour
Naples Florida: Downtown Electric Moped Tour

Naples Florida: Downtown Electric Moped Tour

CA $96
per adult
100% of travellers recommend
Naples Florida: Downtown Electric Moped Tour
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 $609 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.

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