Pine Ridge Vacations from $541

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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.

The Latest Pine Ridge vacation packages

Price found within the past 48 hours. Click for updated prices.
The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Save 100% on your flight
Price was $883, price is now $541 per person
$541
per person
Aug 29 - Sep 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.6/10 Exceptional! (912 reviews)
We were in town for a family reunion and stayed here. Great hotel, staff was fantastic, room was very comfortable and we will be going to stay there again by October!

Reviewed on Jul 12, 2026

LaPlaya Beach & Golf Resort - A Noble House Resort

LaPlaya Beach & Golf Resort - A Noble House Resort

4.5 out of 5
Vanderbilt Beach
Save 100% on your flight
Price was $2,088, price is now $1,116 per person
$1,116
per person
Aug 29 - Sep 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9/10 Wonderful! (1,009 reviews)
La propiedad está muy bien y el servicio es excelente

Reviewed on Jul 12, 2026

Manasota Key Resort

Manasota Key Resort

2.5 out of 5
Save 100% on your flight
Price was $1,156, price is now $637 per person
$637
per person
Aug 17 - Aug 21
found 5 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Fort Myers (RSW)
9.4/10 Exceptional! (300 reviews)
We LOVED our trip to Manasota Key. Staff was outstanding, room very clean, beach was awesome. Enjoyed every minute. We will be back.

Reviewed on Jul 10, 2026

Casa Ybel Resort

Casa Ybel Resort

2.5 out of 5
Mid Island
Save 100% on your flight
Price was $1,331, price is now $858 per person
$858
per person
Aug 25 - Aug 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.8/10 Excellent! (372 reviews)
The property was well restored and maintained. Staff (at the pool) needs to level up.

Reviewed on Jul 10, 2026

The Suites at Fishermen’s Village- 2 Bedroom Suites

The Suites at Fishermen’s Village- 2 Bedroom Suites

3 out of 5
Punta Gorda Isles
Save 100% on your flight
Price was $1,131, price is now $744 per person
$744
per person
Aug 19 - Aug 26
found 2 hours ago
Roundtrip flight included
New York (JFK) to Fort Myers (RSW)
9.8/10 Exceptional! (1,248 reviews)
The suites are great. We stayed at a 2 bedroom suite and it was very comfortable. Two elevators were not working and the pool was not appealing since it was very small, near the parking and only a couple of umbrellas in good condition. We planned to fish from shore but when we arrived, we were informed that we couldn't.

Reviewed on Jul 10, 2026

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What to do in Pine Ridge

Naples Sightseeing Boat Tour

Naples Sightseeing Boat Tour

$57
per adult
96% of travellers recommend
Naples Sightseeing Boat Tour
Gulf of Mexico Sunset Cruise from Naples

Gulf of Mexico Sunset Cruise from Naples

$66
per adult
88% of travellers recommend
Gulf of Mexico Sunset Cruise from Naples
Sunset Tour in Naples Bay on a New Godfrey- All included

Naples Florida Sunset Cruise-Complimentary Charcuterie and wine

$110
per adult
100% of travellers recommend
Naples Florida Sunset Cruise-Complimentary Charcuterie and wine
See all activities in Pine Ridge

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
$274 nightly
The price is $306 total per night from Aug 10 to Aug 11
$306 total
Aug 10 - Aug 11
Total with taxes and fees
9/10 Wonderful! (2,318 reviews)
"Great amenities and really good food at all the eateries.. You get the best of both worlds. Beach and cool pool…"

Reviewed on Jul 10, 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
$139 nightly
The price is $154 total per night from Aug 2 to Aug 3
$154 total
Aug 2 - Aug 3
Total with taxes and fees
9/10 Wonderful! (1,879 reviews)
"This is a very nice hotel, great location, very professional staff, clean and vey nice rooms. Only thing I find negative is that they charge $30.00 per day to park my car. I never stayed at a hotel that charge a fee to park my car. I would stay again but only if parking my car was free."

Reviewed on Jul 12, 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
$199 nightly
The price is $221 total per night from Jul 14 to Jul 15
$221 total
Jul 14 - Jul 15
Total with taxes and fees
9.4/10 Exceptional! (1,054 reviews)
"Over packed and over priced. Too many people to actually enjoy anything."

Reviewed on Jul 12, 2026

Great Wolf Lodge Naples
See all 11,739 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.

Find the Best Pine Ridge Vacation Packages

Pine Ridge Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Southwest Florida Intl. Airport (RSW)
Population
1,900
Max Temp Winter
75ºF
Max Temp Summer
90ºF
Top Sights
Naples Beach, Vanderbilt Beach and Barefoot Beach

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Frequently asked questions

How much does a Pine Ridge vacation package cost?
Offering excellent value package deals from $541 on Expedia, you'll be pleasantly surprised at how much a vacation to Pine Ridge costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Pine Ridge?
If you'd like to snag a cheap Pine Ridge vacation package, consider planning a trip in September, October and December. You're likely to find lower prices on hotels and airfares during these months — perfect for travelers wishing to save money.
How many days is enough for Pine Ridge?
Typically, a handful of days is enough to explore the top attractions during your Pine Ridge vacation. But if you want to have more time to kick back or go on day tours, consider extending your itinerary.
How to find the best Pine Ridge package deals?
Landing a cheap Pine Ridge package deal is easy with Expedia. After you've entered your travel dates and destination under our "Packages" tab, set your budget, add some filters and browse what's available. You can tweak your search by "Amenities," "Property type," "Traveler experience" and more. Order the results by "Price: low to high" to discover the most pocket-friendly Pine Ridge package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Pine Ridge vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your flight, hotel and car rental into one great-value price and enjoy significant savings. You'll generally snag a better deal than booking each component individually. And you'll still get the freedom to create a customized Pine Ridge vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to Pine Ridge?
If you've got your Pine Ridge vacation dates confirmed, book as early as you can to grab some terrific deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spontaneous getaways? Our last-minute deals are great for jetting off on a whim.
How to plan a trip to Pine Ridge?

  1. Pick your travel dates: The things you want to do in Pine Ridge and your favorite season will help you decide when to go.
  2. Plan your budget wisely: As well as the price of your accommodations, you'll need to consider other expenses. These include food, flights and transportation. Also, put aside some extra funds for unexpected expenses that could arise during your trip to Pine Ridge.
  3. Explore Pine Ridge using Expedia's trip planning tool: Gain insights into the top attractions and best hotels for your trip to Pine Ridge. You can also save your favorite places, collaborate with family and friends and manage your plans in one place.
  4. Decide how many days away: Start by compiling a list of the attractions you'd like to get to in Pine Ridge. Then, estimate how long you'll need for each, along with any travel time.
  5. Combine your hotel and flights: Awesome destination, check. Length of stay, check. Now all that's left is to find a Pine Ridge vacation package that brings all your bookings together.
  6. Book any activities or day trips: Here's the fun part — organizing everything you want to see and do. Browse some of the best things to do in Pine Ridge in Pine Ridge and reserve your tickets in advance to save time (and maybe some money too!).

Does Expedia offer Book Now, Pay Later Pine Ridge vacation packages?
Secure your perfect trip to Pine Ridge with our Book Now, Pay Later vacations. There's no need to scrimp and save or wait for the next payday — we've teamed up with online lender Affirm to give you financial flexibility. Our vacation packages with payment plans let you spread the cost across 3, 6 or 12 months. With no late payment fees or hidden charges, you can easily budget for your trip and snap up bargains while they last.

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.