
Southwest Florida Vacation Packages
Book a Stay + Flight or Car to save on your trip
Top Southwest Florida vacation package deals
Price found within the past 48 hours. Click for updated prices.

2.0-star property
Barcelona Studios Guesthouse
South Beach
9.2/10 Wonderful! (98 reviews)
Oct 25 - Nov 2
8 night stay
Boston (BOS) to Miami (MIA)
American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,044, price is now $554 per person
$554
per person
found 1 day ago
Great location near lots of dining options and to the beach. Easy and convenient.
Reviewed on Apr 13, 2025

4.0-star property
Hotel Colonnade Coral Gables, Autograph Collection
Coral Gables Section
9.2/10 Wonderful! (1,006 reviews)
Nov 11 - Nov 14
3 night stay
Boston (BOS) to Miami (MIA)
American Airlines • Roundtrip • Coach
Price was $1,621, price is now $694 per person
$694
per person
found 1 day ago
I tried to contact multiple times the Manager and she avoided me. She sent me a generic emai. Very rude. The property only offers valet parking and in the website they advertise as Parking Available and only tells you about the valet parking fee. Parking in this area is Extremely inconvenient and Expensive. Be careful.
Reviewed on Jun 22, 2024

3.5-star property
Henrosa Hotel
South Beach
8.4/10 Very Good! (818 reviews)
Dec 3 - Dec 8
5 night stay
Boston (BOS) to Miami (MIA)
Spirit Airlines • Non-stop roundtrip • Coach
Price was $1,745, price is now $832 per person
$832
per person
found 1 day ago
For the price that I paid for this hotel room, the experience was great. It is one block from the beach and Starbucks. It is a comfortable Hotel, without being too expensive. I chose this hotel for the price and the proximity to the beach.
Reviewed on Aug 20, 2025


3.5-star property
The Local House
South Beach
9.2/10 Wonderful! (1,003 reviews)
Nov 27 - Dec 2
5 night stay
Boston (BOS) to Miami (MIA)
Frontier Airlines • Non-stop • Coach
Miami (MIA) to Boston (BOS)
Spirit Airlines • Non-stop • Coach
Price was $1,632, price is now $864 per person
$864
per person
found 1 day ago
Very clean and cute room. Need more towels. Very good location close to beach and many nice restaurants.
The first guy who did our check-in was very nice but the other guy who was working at the lobby on our last day knocked our room to put us out when I was taking shower. He didn’t know we paid for late check-out. It was not nice. Otherwise, we enjoyed staying.
Reviewed on Jun 14, 2025
Top rated hotels for your Southwest Florida vacation package

Kompose Boutique Hotel
965 University Pkwy, Sarasota, FL
Free Cancellation
Reserve now, pay when you stay
67.02 mi from city center
$71 nightly
The price is $81 total per night
$81 total
Sep 22 - Sep 23
Total with taxes and fees
At Kompose Boutique Hotel, guests enjoy an outdoor pool, a 24-hour gym, and free WiFi in public areas. Self parking is offered for USD 5.35 per night. The front desk has multilingual staff standing by 24 hours a day to assist with securing valuables and luggage storage. Additional amenities include a hot tub, a 24-hour business center, and a microwave in a common area.
Pool
Hot Tub

Naples Grande Beach Resort
475 Seagate Drive, Naples, FL
Free Cancellation
Reserve now, pay when you stay
32.58 mi from city center
$226 nightly
The price is $251 total per night
$251 total
Sep 28 - Sep 29
Total with taxes and fees
Guests of Naples Grande Beach Resort have access to a full-service spa, 3 outdoor pools, and a 24-hour gym. Parking is available for USD 20 per night (USD 30 per night for valet parking), and there's also a free beach shuttle. The 24-hour front desk has multilingual staff ready to assist with dry cleaning/laundry, tours or tickets, and luggage storage. Other amenities at this beach resort include a sauna, outdoor tennis courts, and free WiFi in public areas.
Pool
Hot Tub

Margaritaville Beach Resort Fort Myers
251 Crescent Street, Fort Myers Beach, FL
18.71 mi from city center
$224 nightly
The price is $250 total per night
$250 total
Sep 29 - Sep 30
Total with taxes and fees
At Margaritaville Beach Resort Fort Myers , guests enjoy a full-service spa, an outdoor pool, and a 24-hour gym. Valet parking is available for USD 35 per day. The front desk is staffed 24 hours a day to help with concierge services and dry cleaning/laundry. This beach hotel also has free WiFi in public areas.
Pool
Spa
Don't see what you're looking for?
See all available properties in Southwest Florida
View all propertiesLowest 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.
More trip options
- Nearby Destinations
- Destinations similar to Southwest Florida
- Best neighborhoods in Southwest Florida
- More to explore for Southwest Florida
- Top trending
- Book on Expedia
Top trending
Hotels
- South Florida Hotels with a Lazy River
- South Florida Kid Friendly Hotels
- South Florida Waterpark Hotels & Resorts
- Central East Coast Florida Beach Resorts & Hotels
- Fort Walton Beach - Destin Waterpark Hotels & Resorts
- Florida Panhandle Beach Resorts & Hotels
- South Florida Hotels with Waterslides
- Sanibel Captiva Island All Inclusive Resorts & Hotels
- Fort Walton Beach - Destin Hotels with Bar
- Florida Panhandle All Inclusive Resorts & Hotels
- Central Florida Cheap Hotels
- Anna Maria Island Hotel Deals
- Fort Walton Beach - Destin All Inclusive Resorts & Hotels
- Hutchinson Island Oceanfront Hotels
- Fort Walton Beach - Destin Hotels with a Lazy River
- Hutchinson Island Hotel Deals
- Fort Walton Beach - Destin Kid Friendly Hotels
- Sanibel Captiva Island Kid Friendly Hotels
- Sanibel Captiva Island Hotel Deals
- Santa Rosa Island Oceanfront Hotels
Flights