Southwest Florida Vacation Packages
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Top Southwest Florida vacation package deals
Price found within the past 48 hours. Click for updated prices.
3.5-star property
The Local House
South Beach
9.2/10 Wonderful! (1,001 reviews)
Dec 17 - Dec 23
6 night stay
Boston (BOS) to Miami (MIA)
Allegiant Air • Coach
Miami (MIA) to Boston (BOS)
Southwest Airlines • Coach
Save 100% on your flight
Price was $1,767, price is now $955 per person
$955
per person
found 1 day ago
The hotel has a great atmosphere. The check in lady was very nice she explained everything on details . Beach was just a block from the hotel . Love this hotel and definitely recommend it . Restaurant is downstairs too and very convenient
Reviewed on Oct 5, 2026
3.5-star property
Private Oasis at Arya
Coconut Grove
8.6/10 Excellent! (1,050 reviews)
Nov 13 - Nov 18
5 night stay
Boston (BOS) to Miami (MIA)
Delta • Roundtrip • Coach
Save 100% on your flight
Price was $1,548, price is now $858 per person
$858
per person
found 1 day ago
Todo excelente
Reviewed on Oct 8, 2026
5.0-star property
1 Hotel South Beach
South Beach
9.4/10 Exceptional! (1,654 reviews)
Dec 28 - Jan 2
5 night stay
Boston (BOS) to Miami (MIA)
Delta • Coach
Miami (MIA) to Boston (BOS)
Southwest Airlines • Coach
Save 100% on your flight
Price was $9,640, price is now $5,364 per person
$5,364
per person
found 1 day ago
All good overall.
Reviewed on Oct 8, 2026
3.5-star property
Cavalier Hotel South Beach
South Beach
8.6/10 Excellent! (1,008 reviews)
Dec 9 - Dec 13
4 night stay
Boston (BOS) to Miami (MIA)
Delta • Coach
Miami (MIA) to Boston (BOS)
Allegiant Air • Coach
Save 100% on your flight
Price was $858, price is now $478 per person
$478
per person
found 1 day ago
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
$65 nightly
The price is $73 total per night
$73 total
Oct 20 - Oct 21
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 luggage storage and securing valuables. Additional amenities include a hot tub, a 24-hour business center, and a microwave in a common area.
Pool
Hot Tub
Compass Hotel by Margaritaville Anna Maria Sound
12324 Manatee Avenue West Bradenton FL
Free Cancellation
Reserve now, pay when you stay
78.48 mi from city center
$176 nightly
The price is $198 total per night
$198 total
Nov 1 - Nov 2
Total with taxes and fees
At Compass Hotel by Margaritaville Anna Maria Sound, guests enjoy features like an outdoor pool, a 24-hour gym, and free WiFi in public areas. There's free parking if you drive. The 24-hour front desk has multilingual staff ready to assist with luggage storage, securing valuables, and concierge services. Additional amenities include conference space, coffee/tea in a common area, and a microwave in a common area.
Pool
Breakfast included
Margaritaville Beach Resort Fort Myers
251 Crescent Street Fort Myers Beach FL
Free Cancellation
Reserve now, pay when you stay
18.71 mi from city center
$202 nightly
The price is $226 total per night
$226 total
Oct 27 - Oct 28
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. Other amenities at this beach hotel include free WiFi in public areas, a business center, and a terrace.
Pool
Spa
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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.
Things to do
Palm Beach: Sightseeing Catamaran Cruise
$61
per adult
92% of travellers recommend
Private Snorkeling Adventure with the Ultimate Local Expert
$110
per adult
98% of travellers recommend
Craft Beer and Wine Sunset Cruise in Palm Beach
$59
per adult
100% of travellers recommend
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