Southwest Florida Luxury Vacations

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Flight and Luxury hotel deals in Southwest Florida

Price found within the past 48 hours. Click for updated prices.
Casey Key Resorts - Mainland

Casey Key Resorts - Mainland

CA $1,090
per person
Nov 3 - Nov 10
found 19 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Sarasota (SRQ)
8.6/10 Excellent! (1,246 reviews)
LaPlaya Beach & Golf Resort - A Noble House Resort

LaPlaya Beach & Golf Resort - A Noble House Resort

Vanderbilt Beach
Save 100% on your flight
CA $3,615
per person
Dec 11 - Dec 18
found 1 day ago
Roundtrip flight included
Comox (YQQ) to Fort Myers (RSW)
9/10 Wonderful! (1,004 reviews)
The resort is under construction and what would have been a beautiful, peaceful beach experience was marred by the noise. Unsettling and disturbing would describe the feeling of laying out in lounge chairs at the beach. When I went to rent a paddle board I was told that the beach rental company, located on the beach at LaPlaya, had lost their contract with LaPlaya consequently they were not allowed to rent equipment to hotel customers. Although the hotel has a restaurant there is no dinning or shopping choices within walking distance. A car is a must. There are lots of choices off highway 41, several miles from the hotel. It wasn’t clear when I booked the hotel that a “Bay View” was not in the main building and was located across the street. Despite umbrellas being readily available, if it’s pouring rain, which it often does, you will get wet crossing the street. The hotel room was very quiet. It might have something to do with being located across the street from the construction. The bell service and housekeeping were exceptional. My room was impeccably cleaned each of the 6 days I spent at LaPlaya. There are 4 pools at the hotel. It would have been nice if at least one of them were adult only, screaming, crying children are not my thing. Our balcony was a shared public space. The hotel only offers valet parking at $44 dollars plus tax per day. I believe once the construction is completed the LaPlaya would be a more satisfying vacation.

Reviewed on Sep 28, 2026

Sundial Beach Resort & Spa

Sundial Beach Resort & Spa

Mid Island
CA $1,533
per person
Nov 4 - Nov 8
found 18 hours ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
8.6/10 Excellent! (2,690 reviews)
Naples Beach Club, A Four Seasons Resort

Naples Beach Club, A Four Seasons Resort

Coquina Sands
Save 100% on your flight
CA $6,890
per person
Dec 22 - Dec 27
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Fort Myers (RSW)
9.6/10 Exceptional! (38 reviews)
Inn on Fifth

Inn on Fifth

Old Naples
CA $5,164
per person
Dec 19 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Fort Myers (RSW)
9.4/10 Exceptional! (1,005 reviews)
A/C noise , I can’t rest good for that.

Reviewed on Sep 27, 2026

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5* Luxury holidays in Southwest Florida

Price found within the past 48 hours. Click for updated prices.
Sundial Beach Resort & Spa

Sundial Beach Resort & Spa

Mid Island
CA $1,533
per person
Nov 4 - Nov 8
found 18 hours ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
8.6/10 Excellent! (2,690 reviews)
Naples Beach Club, A Four Seasons Resort

Naples Beach Club, A Four Seasons Resort

Coquina Sands
Save 100% on your flight
CA $6,890
per person
Dec 22 - Dec 27
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Fort Myers (RSW)
9.6/10 Exceptional! (38 reviews)
The Ritz-Carlton, Sarasota

The Ritz-Carlton, Sarasota

Central Sarasota
CA $3,762
per person
Nov 29 - Dec 5
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Tampa (TPA)
9.2/10 Wonderful! (1,021 reviews)
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3 Night Luxury holidays in Southwest Florida

Price found within the past 48 hours. Click for updated prices.
Casey Key Resorts - Mainland

Casey Key Resorts - Mainland

CA $760
per person
Nov 30 - Dec 3
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Sarasota (SRQ)
8.6/10 Excellent! (1,246 reviews)
Sundial Beach Resort & Spa

Sundial Beach Resort & Spa

Mid Island
Save 100% on your flight
CA $1,114
per person
Nov 12 - Nov 15
found 1 day ago
Roundtrip flight included
Burlington (BTV) to Fort Myers (RSW)
8.6/10 Excellent! (2,690 reviews)
Naples Beach Club, A Four Seasons Resort

Naples Beach Club, A Four Seasons Resort

Coquina Sands
Save 100% on your flight
CA $7,050
per person
Nov 12 - Nov 15
found 1 day ago
Roundtrip flight included
Burlington (BTV) to Fort Myers (RSW)
9.6/10 Exceptional! (38 reviews)
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4 Night Luxury holidays in Southwest Florida

Price found within the past 48 hours. Click for updated prices.
The Lighthouse Resort Inn & Suites

The Lighthouse Resort Inn & Suites

CA $860
per person
Oct 28 - Nov 1
found 1 hour ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Myers (RSW)
8.6/10 Excellent! (1,790 reviews)
Tween Waters Island Resort & Spa

Tween Waters Island Resort & Spa

Save 100% on your flight
CA $1,099
per person
Nov 4 - Nov 8
found 18 hours ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
8.6/10 Excellent! (1,002 reviews)
Sundial Beach Resort & Spa

Sundial Beach Resort & Spa

Mid Island
CA $1,533
per person
Nov 4 - Nov 8
found 18 hours ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
8.6/10 Excellent! (2,690 reviews)
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Plan the perfect luxury Southwest Florida vacation with Expedia

What are some benefits when booking luxury Southwest Florida vacations?

When you book a luxury Southwest Florida vacation, you get to enjoy some of the best amenities and special features available. Luxury vacation options often feature spa facilities right in your accommodation, along with room service and an on-site restaurant. The quality of the bedding and even the water pressure tends to be better, so it's the perfect solution for travellers looking to put their feet up and relax.

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

If you're looking for something luxurious in Southwest Florida, all you have to do is take advantage of our search filters. You can implement a filter to only show 5-star accommodations as well as some amenities you may be interested in, like spa facilities and hot tubs. When you opt for an all-inclusive package, you can enjoy luxury alongside a potential discount for booking your accommodation and flight together.

Can I book a cheap luxury vacation?

While luxury vacations tend to be on the more costly end of the spectrum, ranging from CA $760, there are a few methods you can try to lower the price as much as possible. When booking a flight and accommodation together, you can enjoy savings of up to 22. After implementing filters for luxury features, you can also sort by price to list the cheapest luxury packages first.

Are there luxury spa vacations?

Yes, luxury spa vacations are available and quite popular in Southwest Florida. When you book one of these experiences, it's easier than ever to relax, unwind and recharge in between excursions. Either way, you can easily find spa vacations by implementing the spa filter in your search.

What should I look for in a luxury family vacation in Southwest Florida?

When booking something for the whole family, it's important to consider exactly what kind of experience your family will want.Luxury packages make it easy to keep everyone happy with creature comforts. Kids especially enjoy features like pools, a delicious breakfast and plenty of space. Suites tend to offer your family members a bit more privacy and comfort compared to simple rooms throughout Southwest Florida.

Can I book last-minute luxury vacations?

Yes, last-minute bookings are often available in Southwest Florida. All you have to do is enter your travel dates to see what's available. Sometimes, you'll even find additional discounts for booking last-minute, as accommodations are desperate to fill their last remaining spaces.

What can help me find the best luxury vacation deals in Southwest Florida?

You can use a few strategies to find the best deals on luxury vacation packages. Consider travelling during the off-season to take advantage of the typically lower overall prices. Additionally, staying in the less popular parts of Southwest Florida or travelling to more obscure destinations altogether can often lead to lower prices.

Can I book a luxury vacation that is fully refundable?

Yes, fully refundable reservations are sometimes available on luxury vacation packages in Southwest Florida. You can implement a filter for it specifically or check out the policy section on any one of your search results. It should clearly state what's necessary to qualify for a fully refundable booking.

Why should I book my luxury vacation with Expedia?

When you book with Expedia, you can enjoy a one-stop shop for all your travel planning needs. We offer accommodations as well as flights, and you may even be able to enjoy discounts by booking them together. Of course, Expedia Rewards members will find even more discounts and earn points that can be put toward discounts on future bookings.

Luxury Hotels in Southwest Florida

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
Book a stay at this luxury hotel in Punta Gorda. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in ...
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
Book a 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 ...
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
Book a stay at this luxury hotel in Sarasota. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular ...
The Ritz-Carlton, Sarasota
See all 47,615 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

CA $85
per adult
92% 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

CA $83
per adult
100% of travellers recommend
Craft Beer and Wine Sunset Cruise in Palm Beach
Palm Beach: Floatilla Party Cruise

Palm Beach: Floatilla Party Cruise

CA $144
per adult
Palm Beach: Floatilla Party Cruise
See all activities in Southwest Florida

More vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.