Luxury Vacations in Southwest Florida 2026

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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

CA $832

per person

Oct 7 - Oct 11

found 1 day ago

Roundtrip flight included

Detroit (DTT) to Sarasota (SRQ)

8.8/10 Excellent! (1,234 reviews)

Sundial Beach Resort & Spa

Mid Island

CA $2,437

per person

Sep 14 - Sep 21

found 17 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Fort Myers (RSW)

8.6/10 Excellent! (2,675 reviews)

It was clean The rooms were a good size And the beach was well maintained

Reviewed on Aug 8, 2026

Naples Beach Club, A Four Seasons Resort

Coquina Sands

CA $2,795

per person

Sep 14 - Sep 19

found 1 hour ago

Roundtrip non-stop flight included

Toronto (YYZ) 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 Aug 2, 2026

LaPlaya Beach & Golf Resort - A Noble House Resort

Vanderbilt Beach

CA $1,516

per person

Sep 14 - Sep 19

found 1 hour ago

Roundtrip non-stop flight included

Toronto (YYZ) to Fort Myers (RSW)

9/10 Wonderful! (1,010 reviews)

Naples Bay Resort & Marina

Oyster Bay

CA $1,706

per person

Oct 11 - Oct 17

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) to Fort Myers (RSW)

9.4/10 Exceptional! (1,019 reviews)

Love the location and the amenities

Reviewed on Aug 11, 2026

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5* Luxury holidays in Southwest Florida

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

The Ritz-Carlton, Sarasota

Central Sarasota

CA $2,076

per person

Oct 12 - Oct 16

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Tampa (TPA)

9.2/10 Wonderful! (1,003 reviews)

Excelente!

Reviewed on Aug 10, 2026

Sundial Beach Resort & Spa

Mid Island

CA $2,437

per person

Sep 14 - Sep 21

found 17 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Fort Myers (RSW)

8.6/10 Excellent! (2,675 reviews)

It was clean The rooms were a good size And the beach was well maintained

Reviewed on Aug 8, 2026

Naples Beach Club, A Four Seasons Resort

Coquina Sands

CA $2,795

per person

Sep 14 - Sep 19

found 1 hour ago

Roundtrip non-stop flight included

Toronto (YYZ) to Fort Myers (RSW)

9.6/10 Exceptional! (25 reviews)

Reviewed on Aug 2, 2026

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3 Night Luxury holidays in Southwest Florida

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

Naples Bay Resort & Marina

Oyster Bay

CA $1,005

per person

Oct 23 - Oct 26

found 24 hours ago

Roundtrip flight included

Toronto (YYZ) to Fort Myers (RSW)

9.4/10 Exceptional! (1,019 reviews)

Love the location and the amenities

Reviewed on Aug 11, 2026

Sundial Beach Resort & Spa

Mid Island

CA $1,299

per person

Oct 2 - Oct 5

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Fort Myers (RSW)

8.6/10 Excellent! (2,675 reviews)

It was clean The rooms were a good size And the beach was well maintained

Reviewed on Aug 8, 2026

Inn on Fifth

Old Naples

CA $1,198

per person

Oct 23 - Oct 26

found 24 hours ago

Roundtrip flight included

Toronto (YYZ) to Fort Myers (RSW)

9.4/10 Exceptional! (1,002 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 Aug 10, 2026

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4 Night Luxury holidays in Southwest Florida

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

Lani Kai Beachfront Resort

CA $652

per person

Sep 14 - Sep 18

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Fort Myers (RSW)

8.8/10 Excellent! (1,862 reviews)

Tween Waters Island Resort & Spa

CA $1,132

per person

Nov 4 - Nov 8

found 23 hours ago

Roundtrip non-stop flight included

Rochester (ROC) to Fort Myers (RSW)

8.6/10 Excellent! (1,005 reviews)

Very nice place to enjoy and have a good time. Beach across the street, pool bar and restaurants nearby. Super quite and relaxing. We definitely recommend this place and hopefully coming back soon

Reviewed on Aug 10, 2026

Tropical Beach Resorts

South Village

CA $921

per person

Oct 12 - Oct 16

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Tampa (TPA)

9.4/10 Exceptional! (5,695 reviews)

Clean room, friendly staff and great location.

Reviewed on Aug 10, 2026

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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 $652, 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 12. 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

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 ...

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 ...

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

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 ...

9.2/10 Wonderful! (1,013 reviews)

"Excelente!"

Reviewed on Aug 10, 2026

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.