Pine Ridge Vacations from $305

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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.
Matanzas Inn Bayside Resort and Marina

Matanzas Inn Bayside Resort and Marina

3 out of 5
Price was $648, price is now $305 per person
$305
per person
Jan 24 - Jan 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.2/10 Wonderful! (1,001 reviews)
Rooms were very clean, and the staff was amazing.

Reviewed on Dec 23, 2025

Hilton Garden Inn Ft Myers

Hilton Garden Inn Ft Myers

3 out of 5
Villas
Save 100% on your flight
Price was $897, price is now $466 per person
$466
per person
Mar 4 - Mar 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.6/10 Excellent! (1,002 reviews)
Great amenities, pool and spa, clean room, beautiful lobby and good on site restaurant

Reviewed on Dec 9, 2025

Hyatt Vacation Club at Coconut Cove, Bonita Springs

Hyatt Vacation Club at Coconut Cove, Bonita Springs

4 out of 5
Price was $2,998, price is now $1,608 per person
$1,608
per person
Feb 5 - Feb 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
9.2/10 Wonderful! (704 reviews)
Property amenities are great. Nice and spacious suites/apartments. I had a one bedroom and it had everything you would need at home in it. Full kitchen with all you need to use. Will definitely book again. Staffs are friendly and helpful. Location is great as well.

Reviewed on Dec 24, 2025

Innovation Hotel

Innovation Hotel

4 out of 5
Save 100% on your flight
Price was $1,540, price is now $877 per person
$877
per person
Mar 2 - Mar 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.8/10 Exceptional! (527 reviews)
We had a great time! Modern design, great service and friendly.

Reviewed on Dec 14, 2025

South Seas Resort

South Seas Resort

3.5 out of 5
Save 100% on your flight
Price was $1,584, price is now $930 per person
$930
per person
Mar 2 - Mar 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.4/10 Very Good! (1,001 reviews)
Fantastic place for perfect relaxation, hammocks are placed perfectly for a tropical feel staff is outstanding customer service. A top of the cap to Jeff and Anthony at the front desk.

Reviewed on Dec 10, 2025

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Discover the most popular places to visit in Pine Ridge

Vanderbilt Beach

Vanderbilt Beach

If a restful vacation is part of your travel plans, Vanderbilt Beach might be the perfect place to seek out during your trip to North Naples.

Vanderbilt 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 Beach

Naples Beach

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

What to do in Pine Ridge

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

Naples Sunset Cruise - Complimentary Charcuterie and wine

$110
per adult
100% of travellers recommend
Naples Sunset Cruise - Complimentary Charcuterie and wine
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

Naples Grande Beach Resort

Naples Grande Beach Resort

4.5 out of 5
475 Seagate Drive Naples FL
Fully refundable
$466 nightly
The price is $518 total per night from Jan 4 to Jan 5
$518 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
8.8/10 Excellent! (1,991 reviews)
The staff were exceptional, the hotel was very clean and breakfast was fantastic. A fresh coat of paint would be nice in the hallways but overall, just an outstanding place. We would love to come again.

Reviewed on Dec 23, 2025

Naples Grande Beach Resort
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
$155 nightly
The price is $173 total per night from Jan 7 to Jan 8
$173 total
Jan 7 - Jan 8, 2026
Total with taxes and fees
9/10 Wonderful! (1,020 reviews)
Clean rooms lovely view of Beach and pool area.

Reviewed on Dec 22, 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
$454 nightly
The price is $507 total per night from Dec 30 to Dec 31
$507 total
Dec 30 - Dec 31
Total with taxes and fees
8.8/10 Excellent! (1,724 reviews)
The room was spotless. The crew were friendly and helpful. The swimming pool was the biggest I’ve ever seen. The location was perfect. Id come back for sure.

Reviewed on Dec 24, 2025

Margaritaville Beach Resort Fort Myers
See all 11,744 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 $305 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.