Search Deals on
Pine Ridge Vacation Packages

Build your package with 2 more options

Pine Ridge Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Marriott Sanibel Harbour Resort & Spa

Marriott Sanibel Harbour Resort & Spa

4 out of 5
Save 100% on your flight
Price was $489, price is now $355 per person
$355
per person
Sep 17 - Sep 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Fort Myers (RSW)
Book a stay at this spa resort in Fort Myers. Enjoy 3 outdoor pools, a full-service spa, and 4 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Key West Express and Sanibel Island Lighthouse are located nearby.
The staff exceeded my expectations. From check in to check out,

Reviewed on Aug 11, 2026

The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Save 100% on your flight
Price was $2,235, price is now $1,435 per person
$1,435
per person
Nov 4 - Nov 9
found 15 hours ago
Roundtrip non-stop flight included
Hartford (BDL) to Fort Myers (RSW)
Book a stay at this luxury hotel in Naples. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Popular attractions Vanderbilt Beach and Delnor-Wiggins Pass State Park are located nearby.
amazing hotel and amazing service !!!

Reviewed on Aug 11, 2026

Lehigh Resort Club

Lehigh Resort Club

3.5 out of 5
Save 100% on your flight
Price was $896, price is now $589 per person
$589
per person
Oct 31 - Nov 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this golf aparthotel in Lehigh Acres. Enjoy free WiFi, free parking, and a golf course. Popular attractions Veterans Park and Cypress Pines Country Club are located nearby.
Definitely we will back!

Reviewed on Jul 28, 2026

South Seas

South Seas

3.5 out of 5
Save 100% on your flight
Price was $1,214, price is now $848 per person
$848
per person
Sep 19 - Sep 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this beach resort in Captiva. Enjoy 6 outdoor pools, 5 restaurants, and a private beach. Popular attractions Bowman's Beach and Jungle Drums are located nearby.

Casa Ybel Resort

Casa Ybel Resort

2.5 out of 5
Save 100% on your flight
Price was $623, price is now $435 per person
$435
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Fort Myers (RSW)
Book a stay at this beach hotel in Sanibel. Enjoy free WiFi, free parking, and 2 restaurants. Popular attractions Sanibel Island Southern Beach and Sanibel Island Lighthouse are located nearby.

Casa Tiki

Casa Tiki

3 out of 5
Price was $840, price is now $601 per person
$601
per person
Sep 14 - Sep 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Stay at this vacation home in Cape Coral. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Four Mile Cove Ecological Preserve and Coralwood Mall are located nearby.

Sunsuites Villas At Sunseeker Resort, Curio By Hilton

Sunsuites Villas At Sunseeker Resort, Curio By Hilton

4 out of 5
Save 100% on your flight
Price was $1,235, price is now $899 per person
$899
per person
Oct 31 - Nov 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Stay at this hotel in Punta Gorda. Popular attractions Peace River and Bayshore Live Oak Park are located nearby.

Resort Harbour Properties

Resort Harbour Properties

3.5 out of 5
Save 100% on your flight
Price was $1,387, price is now $1,028 per person
$1,028
per person
Oct 14 - Oct 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this beach condo in Fort Myers. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Key West Express and Sanibel Island Lighthouse are located nearby.
The property was clean and absolutely gorgeous. The pictures honestly didn't do it justice. The hospitality was great! The communication was top notch, but they weren't too much at all. Great privacy! Beach was steps away from the elevator. The location was wonderful! It was secluded but everything we needed was very close by. Sanibel Island was a 10 minute drive at most! We are only going to stay at this property in the future.

Reviewed on Aug 11, 2026

Pine Ridge Vacation Packages 3-4 Night Stays

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 $338, price is now $218 per person
$218
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Fort Myers (RSW)
Casa Ybel Resort

Casa Ybel Resort

2.5 out of 5
Mid Island
Save 100% on your flight
Price was $623, price is now $435 per person
$435
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Fort Myers (RSW)
Tween Waters Island Resort & Spa

Tween Waters Island Resort & Spa

3 out of 5
Price was $1,112, price is now $788 per person
$788
per person
Oct 22 - Oct 26
found 19 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
South Seas

South Seas

3.5 out of 5
Price was $1,061, price is now $757 per person
$757
per person
Oct 22 - Oct 26
found 19 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)

Pine Ridge Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Stay Inn & Suites

Stay Inn & Suites

2.5 out of 5
Winkler
Price was $646, price is now $409 per person
$409
per person
Oct 31 - Nov 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Save 100% on your flight
Price was $853, price is now $514 per person
$514
per person
Sep 26 - Oct 3
found 3 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Fort Myers (RSW)
Tween Waters Island Resort & Spa

Tween Waters Island Resort & Spa

3 out of 5
Save 100% on your flight
Price was $1,757, price is now $1,068 per person
$1,068
per person
Oct 14 - Oct 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
South Seas

South Seas

3.5 out of 5
Save 100% on your flight
Price was $1,576, price is now $984 per person
$984
per person
Oct 14 - Oct 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Frontier Airlines
Sun, Aug 30 - Mon, Sep 14
PHL
Philadelphia Intl.
RSW
Southwest Florida Intl.
$102 Roundtrip, found 2 hours ago
$102
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Sun, Aug 30 from Philadelphia Intl. to Southwest Florida Intl., returning Mon, Sep 14, priced at $102 found 2 hours ago
Frontier Airlines
Mon, Nov 16 - Fri, Dec 4
CLE
Hopkins Intl.
RSW
Southwest Florida Intl.
$108 Roundtrip, found 1 day ago
$108
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Nov 16 from Hopkins Intl. to Southwest Florida Intl., returning Fri, Dec 4, priced at $108 found 1 day ago
Frontier Airlines
Sun, Dec 6 - Mon, Dec 7
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$141 Roundtrip, found 1 hour ago
$141
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sun, Dec 6 from O'Hare Intl. to Southwest Florida Intl., returning Mon, Dec 7, priced at $141 found 1 hour ago
Breeze Airways
Wed, Jan 13 - Sat, Jan 16
PSM
Portsmouth Intl.
RSW
Southwest Florida Intl.
$173 Roundtrip, found 5 hours ago
$173
Roundtrip
found 5 hours ago
Select Breeze Airways flight, departing Wed, Jan 13 from Portsmouth Intl. to Southwest Florida Intl., returning Sat, Jan 16, priced at $173 found 5 hours ago