Pine Ridge Vacation Packages

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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.

Top Pine Ridge Vacation Deals

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 CA $1,481, price is now CA $967 per person
CA $967
per person
May 28 - Jun 2
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Fort Myers (RSW)
9.4/10 Exceptional! (1,021 reviews)
Tremendous value with a $.75 shuttle that takes you over the met Aunt’s past bridge in the heart of Fort Myers Beach

Reviewed on Mar 23, 2026

Windward Passage Resort

Windward Passage Resort

2 out of 5
Price was CA $5,448, price is now CA $3,427 per person
CA $3,427
per person
May 7 - May 14
found 9 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Fort Myers (RSW)
No reviews
Marriott Sanibel Harbour Resort & Spa

Marriott Sanibel Harbour Resort & Spa

4 out of 5
Punta Rassa
Price was CA $1,754, price is now CA $1,222 per person
CA $1,222
per person
May 28 - Jun 2
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Fort Myers (RSW)
8.4/10 Very Good! (1,013 reviews)
Really enjoyed our stay, rooms were clean and amenities were great!

Reviewed on Mar 23, 2026

Lani Kai Beachfront Resort

Lani Kai Beachfront Resort

3.5 out of 5
Price was CA $1,414, price is now CA $1,007 per person
CA $1,007
per person
May 28 - Jun 2
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Fort Myers (RSW)
9/10 Wonderful! (1,297 reviews)
Considering the after math of the hurricane we feel that the hotel recovered great. Gracies food was good !staff were very friendly

Reviewed on Mar 24, 2026

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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 $439 per night from Apr 19 to Apr 20
CA $439
CA $559 total
Apr 19 - Apr 20
includes taxes & fees
9/10 Wonderful! (1,960 reviews)
I love the Marguaritaville resorts, Hollywood Beach, Gatlinburg, key West and now Fort Myers. I had to call this time to get a receipt of charges and the desk person acted surprised that I asked. The charges that they emailed me were like $350.00 less than what my pending charge was on credit card ...

Reviewed on Mar 24, 2026

Margaritaville Beach Resort Fort Myers
Great Wolf Lodge Naples

Great Wolf Lodge Naples

2.5 out of 5
3900 City Gate Blvd N. Naples FL
Fully refundableReserve now, pay when you stay
The price is CA $218 per night from Apr 9 to Apr 10
CA $218
CA $243 total
Apr 9 - Apr 10
includes taxes & fees
9.4/10 Exceptional! (584 reviews)
Yes but very expensive

Reviewed on Mar 24, 2026

Great Wolf Lodge Naples
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 $155 per night from Apr 5 to Apr 6
CA $155
CA $172 total
Apr 5 - Apr 6
includes taxes & fees
8.2/10 Very Good! (1,870 reviews)
Vet good service and cleaning

Reviewed on Mar 24, 2026

La Quinta Inn & Suites by Wyndham Naples Downtown
See all 11,804 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

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
Pristine and idyllic beach at sunset in a bright day, Naples, Florida, USA

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
Vanderbilt beach in Naples, Florida

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

What to do in Pine Ridge

Naples Sightseeing Boat Tour

Naples Sightseeing Boat Tour

CA $90
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 $101
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 Sunset Cruise - Complimentary Charcuterie and wine

CA $151
per adult
100% of travellers recommend
Naples Sunset Cruise - Complimentary Charcuterie and wine
See all activities in Pine Ridge

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