Downtown Vacation Packages for 2025

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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
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 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
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. ...
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 ...
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
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 ...
Hilton Naples

Hilton Naples

4 out of 5
5111 Tamiami Trl N, Naples, FL
14.7 km from Downtown
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

Hilton Garden Inn Ft Myers

3 out of 5
12600 University Dr, Fort Myers, FL
26.4 km from Downtown
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 ...
Sanibel Island Beach Resort

Sanibel Island Beach Resort

3 out of 5
1231 Middle Gulf Dr, Sanibel, FL
28.71 km from Downtown
Stay at this 3-star beach hotel in Sanibel. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the restaurant in our reviews. ...
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
Stay at this 4-star business-friendly hotel in Naples. Enjoy free breakfast, free parking, and a 24-hour fitness center. Our guests praise the helpful staff ...
Pink Shell Beach Resort and Marina

Pink Shell Beach Resort and Marina

4 out of 5
275 Estero Blvd, Fort Myers Beach, FL
22.83 km from Downtown
Stay at this 4-star beach resort in Fort Myers Beach. Enjoy free breakfast, 3 outdoor pools, and 3 restaurants. Our guests praise the breakfast and the pool ...
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
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 ...
Doubletree by Hilton Fort Myers at Bell Tower Shops

Doubletree by Hilton Fort Myers at Bell Tower Shops

4 out of 5
13051 Bell Tower Drive, Fort Myers, FL
25.08 km from Downtown
Stay at this 4-star business-friendly hotel in Fort Myers. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
Bayfront Inn Fifth Avenue

Bayfront Inn Fifth Avenue

3.5 out of 5
1221 5th Ave S, Naples, FL
21.98 km from Downtown
Stay at this 3.5-star business-friendly hotel in Naples. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the restaurant and the bar in our ...
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 ...
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 3-star hotel in Naples. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular ...
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
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 ...
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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
Fri, Oct 17 - Sun, Oct 19
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$110 Roundtrip, found 22 hours ago
$110
Roundtrip
found 22 hours ago
Select Spirit Airlines flight, departing Fri, Oct 17 from O'Hare Intl. to Southwest Florida Intl., returning Sun, Oct 19, priced at $110 found 22 hours ago
American Airlines
Wed, Sep 24 - Mon, Sep 29
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$129 Roundtrip, found 3 days ago
$129
Roundtrip
found 3 days ago
Select American Airlines flight, departing Wed, Sep 24 from O'Hare Intl. to Southwest Florida Intl., returning Mon, Sep 29, priced at $129 found 3 days ago
Frontier Airlines
Sun, Sep 14 - Mon, Sep 15
PHL
Philadelphia Intl.
RSW
Southwest Florida Intl.
$129 Roundtrip, found 1 day ago
$129
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, Sep 14 from Philadelphia Intl. to Southwest Florida Intl., returning Mon, Sep 15, priced at $129 found 1 day ago
United
Wed, Sep 24 - Mon, Sep 29
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$142 Roundtrip, found 3 days ago
$142
Roundtrip
found 3 days ago
Select United flight, departing Wed, Sep 24 from O'Hare Intl. to Southwest Florida Intl., returning Mon, Sep 29, priced at $142 found 3 days ago
Delta
Tue, Nov 4 - Sat, Nov 15
EWR
Newark Liberty Intl. Airport
RSW
Southwest Florida Intl.
$147 Roundtrip, found 3 days ago
$147
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Nov 4 from Newark Liberty Intl. Airport to Southwest Florida Intl., returning Sat, Nov 15, priced at $147 found 3 days ago