
Southwest Florida Holidays
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Top Flight + Hotel Deals in Southwest Florida
Price found within the past 48 hours. Click for updated prices.

Hilton Cabana Miami Beach Resort
Mid Beach
Save 100% on your flight
per person
24 Oct - 28 Oct
found 1 day ago
Return flight included
Boston (BOS) to Miami (MIA)
7.6/10 Good! (292 reviews)
The hotel has potential, but cleanliness definitely needs improvement. Our bathroom had hair stuck to the ceiling of the shower and visible mold in some areas, which was off-putting.
Additionally, the parking fees are excessive. Hilton charged $57 + tax for parking, while a lot just two minutes away on foot offered the same service for only $30. For guests already paying a premium to stay here, the parking costs feel unjustified. I’d strongly recommend lowering the price to be more competitive with the surrounding area.
Reviewed on 30 Jul 2025

Park Central South Beach
South Beach
Save 100% on your flight
per person
24 Oct - 28 Oct
found 1 day ago
Return flight included
Boston (BOS) to Miami (MIA)
8.2/10 Very Good! (906 reviews)
The property had just gone under new management, and things were a bit hectic. Unfortunately, we didn’t have TV service during our entire stay. However, the manager, Eric, went above and beyond to make up for the inconvenience—providing $15 food vouchers throughout our visit and waiving the resort fees. What a fantastic way to turn things around and keep a guest happy! Superb team and a perfect location. Be sure to go see Eric and his staff—they’re truly amazing individuals!
Reviewed on 31 Jul 2025


Where to stay in Southwest Florida
Find the best Southwest Florida areas and neighborhoods for the activities you enjoy most. Learn more about Southwest Florida

North Captiva
Visitors to North Captiva enjoy its beaches, and if you want to do some exploring, North Captiva Island Beach is worth a stop.
Top hotels in Southwest Florida

Kompose Boutique Hotel
965 University Pkwy, Sarasota, FL
Fully refundableReserve now, pay when you stay
9/10 Wonderful! (4,233 reviews)
"Wonderful stay every time"
Reviewed on 29 Jul 2025

Naples Grande Beach Resort
475 Seagate Drive, Naples, FL
Fully refundable
The price is €195 per night from 1 Sept to 2 Sept
€195
1 Sept - 2 Sept
includes taxes & fees
9/10 Wonderful! (1,631 reviews)
"Staff are very friendly. Food and service were excellent. People at the pool and beach were great also."
Reviewed on 31 Jul 2025

Sunseeker Resort Charlotte Harbor
5500 Sunseeker Way, 785, Punta Gorda, FL
Fully refundableReserve now, pay when you stay
The price is €210 per night from 16 Aug to 17 Aug
€210
16 Aug - 17 Aug
includes taxes & fees
9/10 Wonderful! (1,278 reviews)
"Beautiful sunsets"
Reviewed on 1 Aug 2025
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.
Popular places to visit

Siesta Key Beach
The soft, white sand on Siesta Key’s award-winning family-friendly beach is perfect for relaxing under a sun umbrella and taking part in a game of volleyball.

Lido Beach
Nothing says holiday like spending a lazy day at Lido Beach, a popular beach in Sarasota. Wander the picturesque gardens or discover the area's beautiful sunsets.

Venice Beach
If a restful holiday is part of your travel plans, Venice Beach might be the perfect place to visit during your trip to Venice.
What to do in Southwest Florida

Sun & Sightseeing Hakuna Matata Catamaran Cruise in Palm Beach
€44
per adult
92% of travellers recommend

Palm Beach: Sightseeing Catamaran Cruise
€47
per adult
100% of travellers recommend
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Packages
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.