Southwest Florida Luxury Vacations 2026

Plan, book, travel with confidence
Better together
Save up to ￥109,000 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

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 plush bedding, designer toiletries, and more. Deluxe ...

Naples Grande Beach Resort

475 Seagate Drive Naples FL

3 hours drive from Siesta Key Beach

Naples Grande Beach Resort is one of the Naples lavish 4.5-star beach properties where you can treat yourself to deep soaking bathtubs and massage services. ...

9/10 Wonderful! (1,956 reviews)

"Room was in bad condition and staff was not helpful. The property finally admitted that they were about to shut down for a complete remodel. Please be certain a complete remodel has been completed before you would ever consider staying in this property."

Reviewed on Jun 8, 2026

The Ritz-Carlton, Sarasota

1111 Ritz Carlton Dr Sarasota FL

12 min drive from Siesta Key Beach

The Ritz-Carlton, Sarasota is a Sarasota luxury 5-star beach property where you can treat yourself to pillowtop beds, designer toiletries, and more. The 2 outdoor ...

9.2/10 Wonderful! (1,013 reviews)

"Excelente!"

Reviewed on Aug 10, 2026

See all 47,293 properties in Southwest Florida

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.