Search Deals onDowntown Vacation Packages
Downtown Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
The Perry Hotel Naples
Save 100% on your flight
Price was $689, price is now $393 per person
$393
per person
Nov 17 - Nov 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Stay at this 4.5-star 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
Save 100% on your flight
Price was $1,421, price is now $711 per person
$711
per person
Nov 17 - Nov 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Stay at this 4.5-star 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.
Hilton Garden Inn Ft Myers
Villas
Save 100% on your flight
Price was $715, price is now $432 per person
$432
per person
Nov 6 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Stay at this 3-star business-friendly hotel in Fort Myers. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Barbara B Mann Hall and Bell Tower Shops are located nearby.
Inn on Fifth
Old Naples
Save 100% on your flight
Price was $1,034, price is now $667 per person
$667
per person
Nov 17 - Nov 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Stay at this 4-star spa hotel in Naples. Enjoy a full-service spa, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Fifth Avenue South and Naples Pier are located nearby.
Hyatt Vacation Club at Coconut Cove, Bonita Springs
Save 100% on your flight
Price was $615, price is now $399 per person
$399
per person
Nov 9 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Stay at this 4-star eco-certified aparthotel in Bonita Springs. Enjoy free WiFi, free parking, and 3 outdoor pools. Popular attractions Coconut Point Mall and Bonita Springs Public Beach are located nearby.
Embassy Suites by Hilton Fort Myers Estero
Save 100% on your flight
Price was $635, price is now $421 per person
$421
per person
Nov 9 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Stay at this 3.5-star business-friendly hotel in Estero. Enjoy free breakfast, free WiFi, and room service. Our guests praise the breakfast and the pool in our reviews. Popular attractions Hertz Arena and Coconut Point Mall are located nearby.
Casa Playa Beach Resort
Save 100% on your flight
Price was $981, price is now $658 per person
$658
per person
Nov 9 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this beach resort in Fort Myers Beach. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Key West Express and Lynn Hall Memorial Park are located nearby.
Bellasera Resort
Old Naples
Save 100% on your flight
Price was $1,503, price is now $1,011 per person
$1,011
per person
Nov 17 - Nov 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this business-friendly condo in Naples. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the bar in our reviews. Popular attractions Fifth Avenue South and Naples Pier are located nearby.
3-4 Night Vacations in Downtown
Price found within the past 48 hours. Click for updated prices.
5-7 Night Vacations in Downtown
Price found within the past 48 hours. Click for updated prices.
Cheap Hotel Deals in Downtown
Lani Kai Beachfront Resort
1400 Estero Blvd, Fort Myers Beach, FL
Stay at this 3.5-star beach hotel in Fort Myers Beach. Enjoy free WiFi, an outdoor pool, and a beach locale. Popular attractions Key West Express and Crescent ...
Marriott Sanibel Harbour Resort & Spa
17260 Harbour Pointe Dr, Fort Myers, FL
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 ...
Margaritaville Beach Resort Fort Myers
251 Crescent Street, Fort Myers Beach, FL
Stay at this 4-star 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 ...
Save an average of 15% on thousands of hotels when you're signed in
Naples Grande Beach Resort
475 Seagate Drive, Naples, FL
Stay at this 4.5-star luxury resort in Naples. Enjoy 3 outdoor pools, a full-service spa, and 4 restaurants. Our guests praise the pool and the helpful staff ...
Hyatt Vacation Club at Coconut Cove, Bonita Springs
11800 Coconut Cove Drive, Bonita Springs, FL
Stay at this 4-star eco-certified aparthotel in Bonita Springs. Enjoy free WiFi, free parking, and 3 outdoor pools. Popular attractions Coconut Point Mall and ...
Hilton Naples
5111 Tamiami Trl N, Naples, FL
Stay at this 4-star business-friendly hotel in Naples. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Hilton Garden Inn Ft Myers
12600 University Dr, Fort Myers, FL
Stay at this 3-star business-friendly hotel in Fort Myers. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our ...
Hyatt House Naples/5th Avenue
1345 5th Avenue South, Naples, FL
Stay at this 3.5-star business-friendly hotel in Naples. Enjoy free breakfast, free WiFi, and a marina. Our guests praise the breakfast and the pool in our reviews. ...
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
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Wed, Jan 21 - Wed, Jan 28
PSM
Portsmouth Intl.
RSW
Southwest Florida Intl.
$107 Roundtrip, found 2 days ago
$107
Roundtrip
found 2 days ago
Mon, Nov 3 - Fri, Nov 14
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$112 Roundtrip, found 17 hours ago
$112
Roundtrip
found 17 hours ago
Tue, Nov 11 - Tue, Nov 18
EWR
Newark Liberty Intl. Airport
RSW
Southwest Florida Intl.
$127 Roundtrip, found 16 hours ago
$127
Roundtrip
found 16 hours ago
Sun, Nov 9 - Thu, Nov 13
PHL
Philadelphia Intl.
RSW
Southwest Florida Intl.
$128 Roundtrip, found 3 days ago
$128
Roundtrip
found 3 days ago
Discover Other Travel Deals
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- Naples Pier Vacations
- Bonita Springs Public Beach Vacations
- Barefoot Beach Vacations
- Vanderbilt Beach Vacations
- Coconut Point Mall Vacations