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Old Naples Vacation Packages

Old Naples Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
The Suites at Fishermen’s Village- 2 Bedroom Suites

The Suites at Fishermen’s Village- 2 Bedroom Suites

3 out of 5
Punta Gorda Isles
Save 100% on your flight
Price was $736, price is now $451 per person
$451
per person
May 11 - May 15
found 11 hours ago
Roundtrip flight included
Cleveland (CLE) to Fort Myers (RSW)
Stay at this condo in Punta Gorda. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Fishermen's Village and Military Heritage Museum are located nearby.
Lehigh Resort Club

Lehigh Resort Club

3.5 out of 5
Joel
Price was $644, price is now $493 per person
$493
per person
May 14 - May 19
found 15 hours ago
Roundtrip flight included
Cleveland (CLE) to Fort Myers (RSW)
Book a stay at this golf resort in Lehigh Acres. Enjoy free WiFi, free parking, and a golf course. Popular attractions Veterans Park and Cypress Pines Country Club are located nearby.
LaPlaya Beach & Golf Resort - A Noble House Resort

LaPlaya Beach & Golf Resort - A Noble House Resort

4.5 out of 5
Vanderbilt Beach
Save 100% on your flight
Price was $2,139, price is now $1,160 per person
$1,160
per person
Apr 28 - May 2
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.
Windward Passage Resort

Windward Passage Resort

2 out of 5
Save 100% on your flight
Price was $2,741, price is now $1,831 per person
$1,831
per person
May 12 - May 17
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 Lynn Hall Memorial Park are located nearby.
Marriott Sanibel Harbour Resort & Spa

Marriott Sanibel Harbour Resort & Spa

4 out of 5
Punta Rassa
Save 100% on your flight
Price was $1,067, price is now $743 per person
$743
per person
May 6 - May 10
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 Sanibel Island Southern Beach are located nearby.
Matanzas Inn Bayside Resort and Marina

Matanzas Inn Bayside Resort and Marina

3 out of 5
Save 100% on your flight
Price was $1,054, price is now $746 per person
$746
per person
May 12 - May 17
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 daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Key West Express and Ostego Bay Marine Science Center are located nearby.
Edison Beach House

Edison Beach House

3.5 out of 5
Save 100% on your flight
Price was $1,021, price is now $730 per person
$730
per person
May 12 - May 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this beach aparthotel in Fort Myers Beach. Enjoy free parking, a beach locale, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Key West Express and Times Square are located nearby.

3-4 Night Vacations in Old Naples

Price found within the past 48 hours. Click for updated prices.
The Suites at Fishermen’s Village- 2 Bedroom Suites

The Suites at Fishermen’s Village- 2 Bedroom Suites

3 out of 5
Punta Gorda Isles
Save 100% on your flight
Price was $736, price is now $451 per person
$451
per person
May 11 - May 15
found 11 hours ago
Roundtrip flight included
Cleveland (CLE) to Fort Myers (RSW)
Marriott Sanibel Harbour Resort & Spa

Marriott Sanibel Harbour Resort & Spa

4 out of 5
Punta Rassa
Save 100% on your flight
Price was $821, price is now $581 per person
$581
per person
May 6 - May 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Windward Passage Resort

Windward Passage Resort

2 out of 5
Save 100% on your flight
Price was $1,677, price is now $1,200 per person
$1,200
per person
May 21 - May 24
found 20 hours ago
Roundtrip flight included
Cleveland (CLE) to Fort Myers (RSW)

5-7 Night Vacations in Old Naples

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
Save 100% on your flight
Price was $1,054, price is now $746 per person
$746
per person
May 12 - May 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
LaPlaya Beach & Golf Resort - A Noble House Resort

LaPlaya Beach & Golf Resort - A Noble House Resort

4.5 out of 5
Vanderbilt Beach
Save 100% on your flight
Price was $2,211, price is now $1,174 per person
$1,174
per person
May 20 - May 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Windward Passage Resort

Windward Passage Resort

2 out of 5
Save 100% on your flight
Price was $2,741, price is now $1,831 per person
$1,831
per person
May 12 - May 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)

Cheap Hotel Deals in Old Naples

Inn on Fifth

Inn on Fifth

4 out of 5
699 5th Ave S Naples FL
Book a stay at this spa hotel in Naples. Enjoy a full-service spa, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
Opens in a new windowInn on Fifth
Hyatt House Naples/5th Avenue

Hyatt House Naples/5th Avenue

3.5 out of 5
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. ...
Opens in a new windowHyatt House Naples/5th Avenue
Bellasera Resort

Bellasera Resort

4 out of 5
221 9th St S Naples FL
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 ...
Opens in a new windowBellasera Resort
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Cove Inn on Naples Bay

Cove Inn on Naples Bay

3 out of 5
900 Broad Avenue South Naples FL
Stay at this hotel in Naples. Enjoy free WiFi, free parking, and a marina. Our guests praise the helpful staff in our reviews. Popular attractions Fifth Avenue ...
Opens in a new windowCove Inn on Naples Bay
The Capri Inn

The Capri Inn

3.5 out of 5
955 7th Ave South Naples FL
Stay at this hotel in Naples. Enjoy breakfast (surcharge), free bicycles on site, and a 24-hour front desk. Our guests praise the breakfast and the helpful staff ...
Opens in a new windowThe Capri Inn
Naples Park Central Hotel

Naples Park Central Hotel

2.5 out of 5
Naples FL
Book a stay at this business-friendly hotel in Naples. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff and the clean ...
Opens in a new windowNaples Park Central Hotel
Hilton Marco Island Beach Resort and Spa

Hilton Marco Island Beach Resort and Spa

4 out of 5
560 S Collier Blvd Marco Island FL
Book a stay at this beach resort in Marco Island. Enjoy a full-service spa, a beach locale, and room service. Our guests praise the pool and the restaurant in ...
Opens in a new windowHilton Marco Island Beach Resort and Spa
Great Wolf Lodge Naples

Great Wolf Lodge Naples

2.5 out of 5
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 ...
Opens in a new windowGreat Wolf Lodge Naples
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.

Frontier Airlines
Mon, Apr 20 - Mon, May 11
CLE
Hopkins Intl.
RSW
Southwest Florida Intl.
$88 Roundtrip, just found
$88
Roundtrip
just found
Select Frontier Airlines flight, departing Mon, Apr 20 from Hopkins Intl. to Southwest Florida Intl., returning Mon, May 11, priced at $88 just found
Frontier Airlines
Sun, Apr 19 - Thu, Apr 30
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$88 Roundtrip, found 8 hours ago
$88
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Sun, Apr 19 from O'Hare Intl. to Southwest Florida Intl., returning Thu, Apr 30, priced at $88 found 8 hours ago
Frontier Airlines
Tue, May 5 - Tue, May 12
PHL
Philadelphia Intl.
RSW
Southwest Florida Intl.
$135 Roundtrip, found 6 hours ago
$135
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Tue, May 5 from Philadelphia Intl. to Southwest Florida Intl., returning Tue, May 12, priced at $135 found 6 hours ago
Spirit Airlines
Mon, Apr 6 - Mon, Apr 13
DTW
Detroit Metropolitan Wayne County
RSW
Southwest Florida Intl.
$147 Roundtrip, just found
$147
Roundtrip
just found
Select Spirit Airlines flight, departing Mon, Apr 6 from Detroit Metropolitan Wayne County to Southwest Florida Intl., returning Mon, Apr 13, priced at $147 just found