Southwest Florida Vacation Packages for 2025

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Southwest Florida Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Save 100% on your flight
per person
Aug 28 - Sep 1
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Miami (MIA)
Stay at this 3.5-star beach hotel in Miami Beach. Enjoy a beach locale, valet parking (surcharge), and a 24-hour front desk. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Collins Avenue Shopping Area and Ocean Drive are located nearby.

B Ocean Resort Fort Lauderdale Beach

B Ocean Resort Fort Lauderdale Beach

4 out of 5
East Fort Lauderdale
Save 100% on your flight
per person
Aug 18 - Aug 25
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Miami (MIA)
Stay at this 4-star beach resort in Fort Lauderdale. Enjoy 2 outdoor pools, 3 restaurants, and a private beach. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Las Olas Beach and Port Everglades are located nearby.

Henrosa Hotel

Henrosa Hotel

3.5 out of 5
South Beach
Save 100% on your flight
per person
Aug 28 - Sep 1
found 17 hours ago
Roundtrip flight included
Baltimore (BWI) to Miami (MIA)
Stay at this 3.5-star hotel in Miami Beach. Enjoy free WiFi, valet parking (surcharge), and a 24-hour front desk. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Collins Avenue Shopping Area and Ocean Drive are located nearby.

Barcelona Studios Guesthouse

Barcelona Studios Guesthouse

2 out of 5
South Beach
Save 100% on your flight
per person
Aug 18 - Aug 25
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Miami (MIA)
Stay at this guesthouse in Miami Beach. Enjoy free WiFi, a garden, and a picnic area. Popular attractions Collins Avenue Shopping Area and Ocean Drive are located nearby.

President Hotel

President Hotel

3.5 out of 5
South Beach
Save 100% on your flight
per person
Aug 28 - Sep 1
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Miami (MIA)
Stay at this 3.5-star hotel in Miami Beach. Enjoy free breakfast, valet parking (surcharge), and a 24-hour front desk. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Collins Avenue Shopping Area and Ocean Drive are located nearby.

President Villa

President Villa

3.5 out of 5
South Beach
Save 100% on your flight
per person
Aug 28 - Sep 1
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Miami (MIA)
Stay at this 3.5-star hotel in Miami Beach. Enjoy free breakfast, valet parking (surcharge), and a 24-hour front desk. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Collins Avenue Shopping Area and Ocean Drive are located nearby.

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Top Hotel Deals

Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
965 University Pkwy, Sarasota, FL
107.92 km from city center
Stay at this 3-star business-friendly hotel in Sarasota. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the pool ...
Naples Grande Beach Resort

Naples Grande Beach Resort

4.5 out of 5
475 Seagate Drive, Naples, FL
52.47 km from city center
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 ...
Lani Kai Beachfront Resort

Lani Kai Beachfront Resort

3.5 out of 5
1400 Estero Blvd, Fort Myers Beach, FL
30.1 km from city center
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 ...
Compass Hotel by Margaritaville Anna Maria Sound

Compass Hotel by Margaritaville Anna Maria Sound

4 out of 5
12324 Manatee Avenue West, Bradenton, FL
126.44 km from city center
Stay at this 4-star hotel in Bradenton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular ...
Sunseeker Resort Charlotte Harbor

Sunseeker Resort Charlotte Harbor

4.5 out of 5
5500 Sunseeker Way, 785, Punta Gorda, FL
40.23 km from city center
Stay at this 4.5-star luxury resort in Punta Gorda. Enjoy 2 outdoor pools, a full-service spa, and 7 restaurants. Our guests praise the pool and the helpful ...
Embassy Suites by Hilton Sarasota, FL

Embassy Suites by Hilton Sarasota, FL

3.5 out of 5
202 North Tamiami Trail, Sarasota, FL
104.18 km from city center
Stay at this 3.5-star business-friendly hotel in Sarasota. Enjoy free breakfast, free WiFi, and room service. Our guests praise the breakfast and the pool in ...
Hyatt House Naples/5th Avenue

Hyatt House Naples/5th Avenue

3.5 out of 5
1345 5th Avenue South, Naples, FL
60.24 km from city center
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. ...
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
84.9 km from city center
Stay at this 4-star 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 ...
Sanibel Island Beach Resort

Sanibel Island Beach Resort

3 out of 5
1231 Middle Gulf Dr, Sanibel, FL
37.16 km from city center
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. ...
Great Wolf Lodge Naples

Great Wolf Lodge Naples

2.5 out of 5
3900 City Gate Blvd N., Naples, FL
58.48 km from city center
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 ...
Spark by Hilton Sarasota Siesta Key Gateway

Spark by Hilton Sarasota Siesta Key Gateway

3 out of 5
6600 S Tamiami Trl, Sarasota, FL
96.39 km from city center
Stay at this 3-star business-friendly hotel in Sarasota. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
DoubleTree by Hilton Sarasota Bradenton Airport

DoubleTree by Hilton Sarasota Bradenton Airport

4 out of 5
8009 15th Street E, Sarasota, FL
108.88 km from city center
Stay at this 4-star business-friendly hotel in Sarasota. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
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
60.5 km from city center
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 ...
The Westin Sarasota

The Westin Sarasota

4 out of 5
100 Marina View Drive, Sarasota, FL
104.09 km from city center
Stay at this 4-star spa hotel in Sarasota. Enjoy a full-service spa, 2 restaurants, and a rooftop terrace. Our guests praise the breakfast and the pool in our ...
Margaritaville Beach Resort Fort Myers

Margaritaville Beach Resort Fort Myers

4 out of 5
251 Crescent Street, Fort Myers Beach, FL
30.13 km from city center
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 ...
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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.

Frontier Airlines
Mon, Aug 11 - Fri, Aug 29
CLE
Hopkins Intl.
RSW
Southwest Florida Intl.
$68 Roundtrip, found 6 days ago
$68
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Mon, Aug 11 from Hopkins Intl. to Southwest Florida Intl., returning Fri, Aug 29, priced at $68 found 6 days ago
Spirit Airlines
Mon, Aug 11 - Sat, Aug 16
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$94 Roundtrip, found 19 hours ago
$94
Roundtrip
found 19 hours ago
Select Spirit Airlines flight, departing Mon, Aug 11 from O'Hare Intl. to Southwest Florida Intl., returning Sat, Aug 16, priced at $94 found 19 hours ago
JetBlue Airways
Mon, Aug 18 - Wed, Aug 27
LGA
LaGuardia
TPA
Tampa Intl.
$107 Roundtrip, found 3 days ago
$107
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Mon, Aug 18 from LaGuardia to Tampa Intl., returning Wed, Aug 27, priced at $107 found 3 days ago
Delta
Tue, Oct 28 - Wed, Nov 12
LGA
LaGuardia
SRQ
Sarasota-Bradenton Intl.
$127 Roundtrip, found 19 hours ago
$127
Roundtrip
found 19 hours ago
Select Delta flight, departing Tue, Oct 28 from LaGuardia to Sarasota-Bradenton Intl., returning Wed, Nov 12, priced at $127 found 19 hours ago
United
Tue, Sep 30 - Sat, Oct 25
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 Tue, Sep 30 from Newark Liberty Intl. Airport to Southwest Florida Intl., returning Sat, Oct 25, priced at $137 found 5 days ago