Pine Ridge Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Pine Ridge Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Inn at the Beach
Venice Island
$721
per person
Dec 10 - Dec 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Stay at this hotel in Venice. Enjoy free breakfast, free WiFi, and daily housekeeping. Our guests praise the breakfast and the pool in our reviews. Popular attractions Venice Beach and Nokomis Beach are located nearby.
We like the fact that the room is very clean. The staff is very nice. We have been there multiple times. It’s always been wonderful thank you.
Reviewed on Sep 28, 2026
The Perry Hotel Naples
$973
per person
Dec 15 - Dec 19
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) 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 Barefoot Beach are located nearby.
LaPlaya Beach & Golf Resort - A Noble House Resort
Vanderbilt Beach
$1,386
per person
Dec 15 - Dec 19
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Fort Myers (RSW)
Book a stay at this luxury resort in Naples. Enjoy a full-service spa, 2 restaurants, and a private beach. Our guests praise the helpful staff in our reviews. Popular attractions Vanderbilt Beach and Barefoot Beach are located nearby.
Innovation Hotel
$930
per person
Dec 15 - Dec 19
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Fort Myers (RSW)
Book a stay at this business-friendly hotel in Naples. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Vanderbilt Beach and Barefoot Beach are located nearby.
Every aspect ticked all the boxes.. extremely clean, well built, fully detailed, very futuristic looking, simple, yet tasteful breakfast
HIGHLY recommended if you are in the area
Reviewed on Sep 20, 2026
Landing Furnished Apartments Immokalee Road - Naples
Rural Estates
$873
per person
Dec 15 - Dec 19
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Fort Myers (RSW)
Book a stay at this golf apartment in Naples. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Arrowhead Golf Course and Quail Village Golf Club are located nearby.
Inn at Pelican Bay
Pelican Bay
$1,053
per person
Dec 15 - Dec 19
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Fort Myers (RSW)
Stay at this hotel in Naples. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Vanderbilt Beach and Tiburon Golf Club are located nearby.
The room was very nice and the staff was friendly and helpful the breakfast was ok but Ana was very nice I liked the place I will definitely go back and recommend to all my friends and family
Reviewed on Sep 30, 2026
Top Hotel Deals
Margaritaville Beach Resort Fort Myers
251 Crescent Street Fort Myers Beach FL
Book a stay at this beach hotel in Fort Myers Beach. Enjoy free WiFi, a full-service spa, and 4 restaurants. Our guests praise the pool and the helpful staff ...
La Quinta Inn & Suites by Wyndham Naples Downtown
1555 5th Ave S Naples FL
Book a stay at this business-friendly hotel in Naples. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Lani Kai Beachfront Resort
1400 Estero Blvd Fort Myers Beach FL
Book a stay at this beach hotel in Fort Myers Beach. Enjoy free WiFi, 3 restaurants, and a beach locale. Popular attractions Key West Express and Crescent Beach ...
The Perry Hotel Naples
12155 Tamiami Trail N Naples FL
Book a stay at this luxury hotel in Naples. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Popular attractions Vanderbilt Beach and Barefoot Beach are ...
Hyatt Vacation Club at Coconut Cove, Bonita Springs
11800 Coconut Cove Drive Bonita Springs FL
Book a stay at this golf hotel in Bonita Springs. Enjoy free WiFi, free parking, and 3 outdoor pools. Popular attractions Bonita Springs Public Beach and Hertz ...
Hyatt House Naples/5th Avenue
1345 5th Avenue South Naples FL
Book a stay at this business-friendly hotel in Naples. Enjoy free breakfast, free WiFi, and a marina. Our guests praise the breakfast and the pool in our reviews. ...
Compass by Margaritaville Hotel Naples
4805 Tamiami Trl N Naples FL
Book a stay at this business-friendly hotel in Naples. Enjoy free breakfast, free parking, and a 24-hour fitness center. Our guests praise the helpful staff ...
Fairways Inn of Naples
103 Palm River Blvd Naples FL
Stay at this hotel in Naples. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions ...
Pink Shell Beach Resort and Marina
275 Estero Blvd Fort Myers Beach FL
Book a stay at this beach resort in Fort Myers Beach. Enjoy free breakfast, 3 outdoor pools, and a full-service spa. Our guests praise the breakfast and the ...
The Lighthouse Resort Inn & Suites
1051 5th St Fort Myers Beach FL
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. ...
Naples Bay Resort & Marina
1500 Fifth Ave S Naples FL
Book a stay at this spa hotel in Naples. Enjoy free WiFi, 5 outdoor pools, and a full-service spa. Our guests praise the helpful staff and the clean rooms in ...
Great Wolf Lodge Naples
3900 City Gate Blvd N. Naples FL
Book a stay at this family-friendly hotel in Naples. Enjoy free WiFi, 3 outdoor pools, and 4 restaurants. Popular attractions Paradise Coast Sports Compex and ...
The Ritz-Carlton, Naples
280 Vanderbilt Beach Rd Naples FL
Book a stay at this luxury resort in Naples. Enjoy 2 outdoor pools, a full-service spa, and 5 restaurants. Popular attractions Vanderbilt Beach and Tiburon Golf ...
Hilton Naples
5111 Tamiami Trl N Naples FL
Book a stay at this business-friendly hotel in Naples. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Candlewood Suites Fort Myers Sanibel Gateway by IHG
9740 Commerce Center Ct Fort Myers FL
Book a stay at this business-friendly hotel in Fort Myers. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff in ...
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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Sat, Oct 31 - Sat, Nov 7
BOS
Logan Intl.
RSW
Southwest Florida Intl.
$179
Roundtrip
found 3 hours ago
Sat, Oct 31 - Sat, Nov 7
BOS
Logan Intl.
RSW
Southwest Florida Intl.
$199
Roundtrip
found 3 hours ago
Sat, Oct 31 - Sat, Nov 7
BOS
Logan Intl.
RSW
Southwest Florida Intl.
$199
Roundtrip
found 3 hours ago
Mon, Feb 1 - Mon, Feb 8
MSP
Minneapolis - St. Paul Intl.
RSW
Southwest Florida Intl.
$207
Roundtrip
found 2 days ago
Mon, Nov 23 - Tue, Nov 24
DTW
Detroit Metropolitan Wayne County
RSW
Southwest Florida Intl.
$222
Roundtrip
found 22 hours ago
Best points of interest in Naples
More AARP Member Vacation Packages
- Las Vegas Vacations
- New York Vacations
- Orlando Vacations
- Los Angeles Vacations
- Miami Vacations
- San Francisco Vacations
- New Orleans Vacations
- Chicago Vacations
- Fort Lauderdale Vacations
- Boston Vacations
- Honolulu Vacations
- San Diego Vacations
- Washington Vacations
- Toronto Vacations
- Anaheim Vacations
- Atlanta Vacations
- Nashville Vacations
- Seattle Vacations
- Phoenix Vacations
- Myrtle Beach Vacations
- Vancouver Vacations
- Palm Springs Vacations
- Denver Vacations
- Tampa Vacations
- Niagara Falls Vacations
- San Antonio Vacations
- Atlantic City Vacations
- Philadelphia Vacations
- Austin Vacations
- Dallas Vacations