Southwest Florida Luxury Holidays

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Top flight + Luxury hotel deals in Southwest Florida

Price found within the past 48 hours. Click for updated prices.
Inn on Fifth

Inn on Fifth

Old Naples
£1,206
per person
12 Sept - 19 Sept
found 4 hours ago
Return direct flight included
London (LON) to Fort Myers (RSW)
9.4/10 Exceptional! (1,010 reviews)
1 night stay in a junior suite. Check in was easy, friendly staff. Our room was clean and was just steps from the pool. The location is amazing and an easy walk to all of the 5th Avenue restaurants. Will definitely stay here again.

Reviewed on 10 Aug 2026

Naples Beach Club, A Four Seasons Resort

Naples Beach Club, A Four Seasons Resort

Coquina Sands
£2,584
per person
12 Sept - 19 Sept
found 4 hours ago
Return direct flight included
London (LON) to Fort Myers (RSW)
9.6/10 Exceptional! (25 reviews)
**⭐⭐⭐⭐⭐ A five-star experience — for our pet too!** Our stay at the Four Seasons Resort Naples was simply spectacular from start to finish. From check-in, we were welcomed with genuine warmth, and the attention to detail was felt in every corner: impeccable rooms, breathtaking views of the Gulf of Mexico, and service that anticipates every need before you even ask. What truly surprised us was how well they treated our dog. The staff asked for him by name, brought him water during our walks around the resort, and the "canine concierge" recommended nearby pet-friendly parks and areas. It was clear that for them, pets aren't just "tolerated" — they're genuinely welcomed and pampered. Between the spa, the exceptional restaurants, and the white sand beaches, every moment felt like a well-deserved luxury. Without a doubt, one of the best resorts we've ever stayed at, both for us and for our four-legged companion. We'll definitely be back!

Reviewed on 2 Aug 2026

LaPlaya Beach & Golf Resort - A Noble House Resort

LaPlaya Beach & Golf Resort - A Noble House Resort

Vanderbilt Beach
£2,114
per person
31 Oct - 7 Nov
found 5 hours ago
Return direct flight included
London (LON) to Fort Myers (RSW)
9/10 Wonderful! (1,010 reviews)
Naples Bay Resort & Marina

Naples Bay Resort & Marina

Oyster Bay
£1,297
per person
14 Sept - 21 Sept
found 5 hours ago
Return direct flight included
London (LON) to Fort Myers (RSW)
9.4/10 Exceptional! (1,019 reviews)
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5* Luxury holidays in Southwest Florida

Price found within the past 48 hours. Click for updated prices.
Naples Beach Club, A Four Seasons Resort

Naples Beach Club, A Four Seasons Resort

Coquina Sands
£2,584
per person
12 Sept - 19 Sept
found 4 hours ago
Return direct flight included
London (LON) to Fort Myers (RSW)
9.6/10 Exceptional! (25 reviews)
**⭐⭐⭐⭐⭐ A five-star experience — for our pet too!** Our stay at the Four Seasons Resort Naples was simply spectacular from start to finish. From check-in, we were welcomed with genuine warmth, and the attention to detail was felt in every corner: impeccable rooms, breathtaking views of the Gulf of Mexico, and service that anticipates every need before you even ask. What truly surprised us was how well they treated our dog. The staff asked for him by name, brought him water during our walks around the resort, and the "canine concierge" recommended nearby pet-friendly parks and areas. It was clear that for them, pets aren't just "tolerated" — they're genuinely welcomed and pampered. Between the spa, the exceptional restaurants, and the white sand beaches, every moment felt like a well-deserved luxury. Without a doubt, one of the best resorts we've ever stayed at, both for us and for our four-legged companion. We'll definitely be back!

Reviewed on 2 Aug 2026

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All you need to know about luxury holidays in Southwest Florida

What can I expect from a luxury Southwest Florida holiday?

Luxury on holiday is all about relaxing and feeling good. Whether you choose a sumptuous spa, Michelin-starred restaurant or super-king bed is your call. Use our amenities filters to find the things that tick all your boxes.

How can I find all-inclusive luxury holidays in Southwest Florida?

Tick the all-inclusive and 5-star filters to find the crème de la crème of Southwest Florida holidays. With everything included in the package price, you can drink and dine to your heart’s content, without worrying about that bill at the end.

Can I book a cheap luxury holiday to Southwest Florida?

A luxury holiday doesn’t have to break the bank. Travel out of peak season, choose a hotel or resort a little way out or go for a last-minute getaway and you’ll find some cracking deals. Sort by price to find luxury holidays to Southwest Florida starting at £1,206. Prices and availability are subject to change. Additional terms may apply.

Are there luxury spa holidays in Southwest Florida?

For sunset massages on the shoreline and view-filled saunas, use our spa filter to find your ideal Southwest Florida spa hotel. Book a whole weekend soaking away your stresses, or hop into the spa after the beach, some golf or a local advent-ahhhh.

What should I look for when booking a luxury family holiday in Southwest Florida?

Luxury isn’t just for adults. Those little touches designed for little people make a family holiday genuinely stress free … which is the greatest luxury of all. Look for spacious suites, pools toddlers can splash in, and breakfast buffets with waffles, pancakes and Nutella galore.

Can I book luxury last-minute holidays to Southwest Florida?

You can wangle a top-notch luxury holiday in Southwest Florida for a fraction of the normal price by booking last minute. Just enter your dates and see what’s available – if you’re flexible ... even better!

Can I book a luxury holiday in Southwest Florida with free cancellation and/or flexible dates?

If you’re splashing out on a luxury holiday, make sure your money is safe by booking with free cancellation. Just use the fully refundable filter and make sure you read all the terms and conditions.

Why should I book my luxury travel to Southwest Florida with Expedia?

Nobody does luxury quite like Expedia. With so many gorgeous properties in Southwest Florida to choose from, as well as access to first-class flight deals and hire cars with horsepower, there’s no better place to book.

Top Luxury Southwest Florida Hotels

Wyvern Hotel, an Ascend Collection Hotel

Wyvern Hotel, an Ascend Collection Hotel

101 E Retta Esplanade Punta Gorda FL
  • 1 hour drive from Siesta Key Beach
Stay at this luxury hotel in Punta Gorda. Enjoy free Wi-Fi, free parking and 2 restaurants. Our guests praise the helpful staff and the clean rooms in their ...
Wyvern Hotel, an Ascend Collection Hotel
Naples Grande Beach Resort

Naples Grande Beach Resort

475 Seagate Drive Naples FL
  • 3 hours drive from Siesta Key Beach
Stay at this luxury resort in Naples. Enjoy 3 outdoor pools, a full-service spa and 4 restaurants. Our guests praise the pool and the helpful staff in their ...
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 8 Jun 2026

Naples Grande Beach Resort
The Ritz-Carlton, Sarasota

The Ritz-Carlton, Sarasota

1111 Ritz Carlton Dr Sarasota FL
  • 12 min drive from Siesta Key Beach
Stay at this luxury hotel in Sarasota. Enjoy free Wi-Fi, 2 outdoor pools and a full-service spa. Our guests praise the helpful staff in their reviews. Popular ...
9.2/10 Wonderful! (1,013 reviews)
"Excelente!"

Reviewed on 10 Aug 2026

The Ritz-Carlton, Sarasota
See all 47,330 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.

Things to do

Palm Beach: Sightseeing Catamaran Cruise

Palm Beach: Sightseeing Catamaran Cruise

£46
per adult
100% of travellers recommend
Palm Beach: Sightseeing Catamaran Cruise
Craft Beer and Wine Sunset Cruise in Palm Beach

Craft Beer and Wine Sunset Cruise in Palm Beach

£44
per adult
100% of travellers recommend
Craft Beer and Wine Sunset Cruise in Palm Beach
Private Snorkeling Adventure with the Ultimate Local Expert

Private Snorkeling Adventure with the Ultimate Local Expert

£83
per adult
98% of travellers recommend
Private Snorkeling Adventure with the Ultimate Local Expert
See all activities in Southwest Florida

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.