Pine Ridge Vacations from $355

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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.
Hilton Garden Inn Ft Myers

Hilton Garden Inn Ft Myers

3 out of 5
Villas
Price was $585, price is now $355 per person
$355
per person
Dec 19 - Dec 23
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
8.6/10 Excellent! (1,011 reviews)
Room was clean didn’t use other amenities due to trip schedule. Always greeted by friendly staff.

Reviewed on Oct 13, 2025

Matanzas Inn Bayside Resort and Marina

Matanzas Inn Bayside Resort and Marina

3 out of 5
Save 100% on your flight
Price was $1,065, price is now $608 per person
$608
per person
Dec 19 - Dec 23
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
9.2/10 Wonderful! (1,002 reviews)
Great place! Great location!

Reviewed on Oct 15, 2025

South Seas Resort

South Seas Resort

3.5 out of 5
Save 100% on your flight
Price was $1,338, price is now $835 per person
$835
per person
Dec 19 - Dec 23
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
8.4/10 Very Good! (1,003 reviews)
The room was spotless, and the check-in staff was incredibly friendly. The trolley driver was very accommodating, and the team at the ice cream shop was also warm and welcoming. The beach was absolutely stunning—I keep thinking about how much I want to go back. Swimming with fish all around me was such a memorable experience. Overall, it was an amazing trip for both kids and adults. Thank you!

Reviewed on Oct 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
Save 100% on your flight
Price was $2,403, price is now $1,522 per person
$1,522
per person
Dec 28 - Dec 31
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
8.8/10 Excellent! (1,002 reviews)
Our experience at La Playa was exceptional, everything was what we wanted and expected it to be

Reviewed on Sep 29, 2025

The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Save 100% on your flight
Price was $1,799, price is now $1,205 per person
$1,205
per person
Dec 28 - Dec 31
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
9.6/10 Exceptional! (417 reviews)
I would give it excellent but we checked out around 9pm due to a few hours of the fire alarm going off. They had the fire department there but they were still working on the problem and we were concerned we wouldn’t be able to get a good night’s sleep.

Reviewed on Oct 14, 2025

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Discover the most popular places to visit in Pine Ridge

Naples Beach

Naples Beach

4.5/5(1,407 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

4.5/5(45 reviews)

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 a sandy beach and landscape views as well as a large group of people

Naples Pier

4.5/5(1,161 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

Sunset Tour in Naples Bay on a New Godfrey- All included

Sunset Tour in Naples Bay on a New Godfrey- All included

$100
per adult
100% of travellers recommend
Sunset Tour in Naples Bay on a New Godfrey- All included
Wild Dolphin Boat Tour

Best of Marco Dolphin Tour

$100
per adult
Best of Marco Dolphin Tour
Naples, FL: Manatee, Dolphin, 10,000 Islands Beach Eco Tour

Naples, FL: Manatee, Dolphin, 10,000 Islands Beach Eco Tour

$127
per adult
Naples, FL: Manatee, Dolphin, 10,000 Islands Beach Eco Tour
See all activities in Pine Ridge

Pine Ridge Hotel Deals

Lani Kai Beachfront Resort

Lani Kai Beachfront Resort

3.5 out of 5
1400 Estero Blvd, Fort Myers Beach, FL
Fully refundableReserve now, pay when you stay
$191 nightly
The price is $214 total per night from Oct 22 to Oct 23
$214 total
Oct 22 - Oct 23
Total with taxes and fees
8.8/10 Excellent! (1,033 reviews)
"The thing that i did not like was that the tub was small and we had to pay for parking each day. Everything else was great."

Reviewed on Oct 11, 2025

Lani Kai Beachfront Resort
Margaritaville Beach Resort Fort Myers

Margaritaville Beach Resort Fort Myers

4 out of 5
251 Crescent Street, Fort Myers Beach, FL
$224 nightly
The price is $250 total per night from Nov 4 to Nov 5
$250 total
Nov 4 - Nov 5
Total with taxes and fees
8.8/10 Excellent! (1,531 reviews)
"This was a great resort. I was surprised that the main hotel is across the street from the beach, but there is a bridge that makes it easy to get to the beach, pool and restaurants. We came with our teens and there were lots of families there, which made it enjoyable for all of us."

Reviewed on Oct 11, 2025

Margaritaville Beach Resort Fort Myers
Naples Grande Beach Resort

Naples Grande Beach Resort

4.5 out of 5
475 Seagate Drive, Naples, FL
Fully refundable
$264 nightly
The price is $294 total per night from Oct 27 to Oct 28
$294 total
Oct 27 - Oct 28
Total with taxes and fees
9/10 Wonderful! (1,856 reviews)
"This is a beautiful resort and the staff is obviously very dedicated to making your staff a pleasant one because everyone from the valet attendants to the front desk to the restaurant and bar staff were attentive, professional and pleasant. The shuttle to the beach where the great guys providing ..."

Reviewed on Oct 12, 2025

Naples Grande Beach Resort
See all 11,508 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.

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 $355 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.