Search Deals onPine Ridge Vacation Packages
Pine Ridge Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Latitude 26 Waterfront Resort & Marina
Save 100% on your flight
Price was $934, price is now $489 per person
$489
per person
Nov 7 - Nov 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Stay at this motel in Fort Myers Beach. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Key West Express and Estero Boulevard Beach are located nearby.
The Perry Hotel Naples
Price was $2,638, price is now $1,296 per person
$1,296
per person
Nov 4 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.
For 2 of my 4 day work travel I had to work from the room and there was a dog barking for 3 hrs straight. When I went to check the room number to tell the front desk, it turned out the roof was for STAFF personel!!
There was no welcome card explaining how to get on the WiFi, when food was available, since there's no room service. Hours for amenities.
Room key stopped working twice 2 days in a row when I got back late from working.
Reviewed on Aug 29, 2026
Tween Waters Island Resort & Spa
Save 100% on your flight
Price was $1,627, price is now $893 per person
$893
per person
Oct 31 - Nov 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this beach resort in Captiva. Enjoy free parking, 2 outdoor pools, and a full-service spa. Popular attractions Bowman's Beach and Captiva Beach are located nearby.
No problems
Reviewed on Aug 29, 2026
The Lighthouse Resort Inn & Suites
Save 100% on your flight
Price was $950, price is now $586 per person
$586
per person
Nov 7 - Nov 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Stay at this hotel in Fort Myers Beach. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Key West Express and Estero Boulevard Beach are located nearby.
Great location for Fort Meyers beach. Our room was dated/worn and not particularly clean (bedsheets stained etc). That being said, our room was old in the older part of the resort, so the newer side may be better? On site bar is worth a visit for food/drink
Reviewed on Aug 27, 2026
Lehigh Resort Club
Save 100% on your flight
Price was $794, price is now $491 per person
$491
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.
I like the hotel however needs upgrade they have bicycles and stuff but most they were flat or not working
Reviewed on Aug 20, 2026
Windward Passage Resort
Save 100% on your flight
Price was $1,149, price is now $714 per person
$714
per person
Nov 7 - Nov 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this beach hotel in Fort Myers Beach. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Key West Express and Estero Boulevard Beach are located nearby.
Casa Ybel Resort
Save 100% on your flight
Price was $1,222, price is now $769 per person
$769
per person
Oct 30 - Nov 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 Bowman's Beach are located nearby.
Beautiful clean place room clean beds comfy everything just as described. No complaints will definitely visit again and stay there.
Reviewed on Aug 29, 2026
Marriott Sanibel Harbour Resort & Spa
Save 100% on your flight
Price was $1,417, price is now $898 per person
$898
per person
Nov 7 - Nov 14
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 Estero Boulevard Beach are located nearby.
Pine Ridge Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Pine Ridge Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Fri, Sep 25 - Fri, Oct 9
CLE
Hopkins Intl.
RSW
Southwest Florida Intl.
$125 Roundtrip, found 2 days ago
$125
Roundtrip
found 2 days ago
Sat, Jan 23 - Sat, Feb 6
PSM
Portsmouth Intl.
RSW
Southwest Florida Intl.
$152 Roundtrip, found 4 days ago
$152
Roundtrip
found 4 days ago
Fri, Sep 11 - Sun, Sep 13
PHL
Philadelphia Intl.
RSW
Southwest Florida Intl.
$154 Roundtrip, found 13 hours ago
$154
Roundtrip
found 13 hours ago
Mon, Nov 23 - Thu, Dec 3
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$163 Roundtrip, found 2 days ago
$163
Roundtrip
found 2 days ago
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