Southwest Florida Luxury Vacations

Book a Luxury Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ₩1,660,000 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

Top Luxury Southwest Florida Hotels

Wyvern Hotel, an Ascend Collection Hotel

Wyvern Hotel, an Ascend Collection Hotel

4 out of 5
101 E Retta Esplanade Punta Gorda FL
  • 1 hour drive from Siesta Key Beach
Stay in the lap of luxury at Wyvern Hotel, an Ascend Collection Hotel, where you can enjoy amenities like Champagne service, plush bedding, and more. Deluxe ...
Wyvern Hotel, an Ascend Collection Hotel
Signia Hilton Naples Grande Beach Resort

Signia Hilton Naples Grande Beach Resort

4.5 out of 5
475 Seagate Drive Naples FL
  • 3 hours drive from Siesta Key Beach
Be treated to a grand stay at Signia Hilton Naples Grande Beach Resort, where you'll find deep soaking bathtubs and premium bedding. Deluxe amenities at this ...
Signia Hilton Naples Grande Beach Resort
The Ritz-Carlton, Sarasota

The Ritz-Carlton, Sarasota

5 out of 5
1111 Ritz Carlton Dr Sarasota FL
  • 12 min drive from Siesta Key Beach
Stay in the lap of luxury at The Ritz-Carlton, Sarasota, where you can enjoy amenities like pillowtop beds, designer toiletries, and more. The 2 outdoor pools, ...
9.2/10 Wonderful! (1,020 reviews)
"Very well maintained property. Staff very kind and professional. Our room was spacious and well appointed . The beds were somewhat comfortable , they need better pillows. Also, they need more dining options. Overall, nice property."

Reviewed on Nov 9, 2026

The Ritz-Carlton, Sarasota
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.