Downtown Vacation Packages for 2026

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Top Hotel Deals

Naples Grande Beach Resort

Naples Grande Beach Resort

4.5 out of 5
475 Seagate Drive Naples FL
14.7 km from Downtown
Book a stay at this luxury resort in Naples. Enjoy 3 outdoor pools, a full-service spa, and 4 restaurants. Our guests praise the pool and the helpful staff in ...
Marriott Sanibel Harbour Resort & Spa

Marriott Sanibel Harbour Resort & Spa

4 out of 5
17260 Harbour Pointe Dr Fort Myers FL
28.46 km from Downtown
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

Margaritaville Beach Resort Fort Myers

4 out of 5
251 Crescent Street Fort Myers Beach FL
21.39 km from Downtown
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 ...
Lani Kai Beachfront Resort

Lani Kai Beachfront Resort

3.5 out of 5
1400 Estero Blvd Fort Myers Beach FL
21.15 km from Downtown
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 ...
Holiday Inn Express Cape Coral-Fort Myers Area by IHG

Holiday Inn Express Cape Coral-Fort Myers Area by IHG

2.5 out of 5
1538 Cape Coral Pkwy E Cape Coral FL
29.68 km from Downtown
Book a stay at this business-friendly hotel in Cape Coral. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Fairways Inn of Naples

Fairways Inn of Naples

3 out of 5
103 Palm River Blvd Naples FL
7.5 km from Downtown
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 ...
Sanibel Island Beach Resort

Sanibel Island Beach Resort

3 out of 5
1231 Middle Gulf Dr Sanibel FL
28.71 km from Downtown
Book a stay at this beach hotel in Sanibel. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the restaurant in our reviews. ...
Hyatt Vacation Club at Coconut Cove, Bonita Springs

Hyatt Vacation Club at Coconut Cove, Bonita Springs

4 out of 5
11800 Coconut Cove Drive Bonita Springs FL
9.46 km from Downtown
Book a stay at this golf aparthotel in Bonita Springs. Enjoy free WiFi, free parking, and 3 outdoor pools. Popular attractions Coconut Point Mall and Bonita ...
La Quinta Inn & Suites by Wyndham Naples Downtown

La Quinta Inn & Suites by Wyndham Naples Downtown

2.5 out of 5
1555 5th Ave S Naples FL
22.44 km from Downtown
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 ...
DiamondHead Beach Resort

DiamondHead Beach Resort

3.5 out of 5
2000 Estero Blvd Fort Myers Beach FL
20.68 km from Downtown
Book a stay at this beach resort in Fort Myers Beach. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the helpful staff in ...
The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
12155 Tamiami Trail N Naples FL
7.02 km from Downtown
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 ...
Hilton Naples

Hilton Naples

4 out of 5
5111 Tamiami Trl N Naples FL
14.7 km from Downtown
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 ...
Compass by Margaritaville Hotel Naples

Compass by Margaritaville Hotel Naples

4 out of 5
4805 Tamiami Trl N Naples FL
15.19 km from Downtown
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 ...
Hilton Garden Inn Ft Myers

Hilton Garden Inn Ft Myers

3 out of 5
12600 University Dr Fort Myers FL
26.4 km from Downtown
Book a stay at this 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

Hyatt House Naples/5th Avenue

3.5 out of 5
1345 5th Avenue South Naples FL
22.19 km from Downtown
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. ...
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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.

Spirit Airlines
Tue, Feb 17 - Wed, Feb 25
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$70 Roundtrip, found 1 day ago
$70
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Tue, Feb 17 from O'Hare Intl. to Southwest Florida Intl., returning Wed, Feb 25, priced at $70 found 1 day ago
Frontier Airlines
Sat, Feb 21 - Thu, Feb 26
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$73 Roundtrip, found 1 day ago
$73
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Feb 21 from O'Hare Intl. to Southwest Florida Intl., returning Thu, Feb 26, priced at $73 found 1 day ago
JetBlue Airways
Sun, Feb 1 - Fri, Feb 6
EWR
Newark Liberty Intl. Airport
RSW
Southwest Florida Intl.
$127 Roundtrip, found 1 day ago
$127
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Sun, Feb 1 from Newark Liberty Intl. Airport to Southwest Florida Intl., returning Fri, Feb 6, priced at $127 found 1 day ago
Delta
Sun, Jan 18 - Thu, Jan 22
BOS
Logan Intl.
RSW
Southwest Florida Intl.
$130 Roundtrip, found 2 days ago
$130
Roundtrip
found 2 days ago
Select Delta flight, departing Sun, Jan 18 from Logan Intl. to Southwest Florida Intl., returning Thu, Jan 22, priced at $130 found 2 days ago
United
Sun, Feb 1 - Thu, Feb 5
EWR
Newark Liberty Intl. Airport
RSW
Southwest Florida Intl.
$137 Roundtrip, found 5 days ago
$137
Roundtrip
found 5 days ago
Select United flight, departing Sun, Feb 1 from Newark Liberty Intl. Airport to Southwest Florida Intl., returning Thu, Feb 5, priced at $137 found 5 days ago