Title: Book the Best HISTORIC Hotels in Southwest Florida in 2026 | Expedia.ca

[Southwest Florida Travel Guide](https://expedia.ca/Southwest-Florida.dx6233839)[Hotels in Southwest Florida](https://expedia.ca/Southwest-Florida-Hotels.d6233839.Travel-Guide-Hotels)[Vacation Rentals in Southwest Florida](https://expedia.ca/Southwest-Florida-Vacation-Rentals.d6233839.Travel-Guide-VacationRentals)[Flights to Southwest Florida](https://expedia.ca/Cheap-Flights-To-Southwest-Florida.d6233839.Travel-Guide-Flights)[Things to do in Southwest Florida](https://expedia.ca/Things-To-Do-In-Southwest-Florida.d6233839.Travel-Guide-Activities)[Southwest Florida Car Rentals](https://expedia.ca/Car-Rentals-In-Southwest-Florida.d6233839.Car-Rental-Guide)[Southwest Florida Vacation Packages](https://expedia.ca/Southwest-Florida.d6233839.Destination-Travel-Guides)

![Delnor-Wiggins Pass State Park featuring a sandy beach as well as a couple](https://images.trvl-media.com/place/6065875/bc23d051-1ceb-4c43-a754-b9feb3316d59.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/6065875/bc23d051-1ceb-4c43-a754-b9feb3316d59.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check availability on Southwest Florida Historic Hotels

Tonight

[Mar 19 - Mar 20](https://www.expedia.ca/Hotel-Search?regionId=6233839&startDate=2026-03-19&endDate=2026-03-20&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Mar 20 - Mar 21](https://www.expedia.ca/Hotel-Search?regionId=6233839&startDate=2026-03-20&endDate=2026-03-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=6233839&startDate=2026-03-20&endDate=2026-03-22&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Mar 27 - Mar 29](https://www.expedia.ca/Hotel-Search?regionId=6233839&startDate=2026-03-27&endDate=2026-03-29&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Southwest Florida historic hotels

![Exterior](https://images.trvl-media.com/lodging/72000000/71780000/71773700/71773667/d638d1fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71780000/71773700/71773667/2b29aea1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71780000/71773700/71773667/be06cc75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/72000000/71780000/71773700/71773667/29d055cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Country Cottage, 40 Acres, Outdoor Kitchen w/ B-que, Campfire, & Horse Stables.

[](https://www.expedia.ca/LaBelle-Hotels-Country-Cottage-On-40-Acres.h71773667.Hotel-Information)

LaBelle

9.8/10

Exceptional

(81 reviews)

"The cottage was very clean. It is exactly as described. The host was extremely responsive and very helpful."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Silvana C.

CA $184

CA $353 total

includes taxes & fees

Mar 23 - Mar 24

[](https://www.expedia.ca/LaBelle-Hotels-Country-Cottage-On-40-Acres.h71773667.Hotel-Information)

![Beach nearby, beach towels](https://images.trvl-media.com/lodging/67000000/66060000/66054400/66054317/c128477b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/67000000/66060000/66054400/66054317/edfdd191.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/67000000/66060000/66054400/66054317/273cc0e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/67000000/66060000/66054400/66054317/6fb611a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Old Floridian cottage in Historic Gulf Village

[](https://www.expedia.ca/Port-Charlotte-Charlotte-Harbor-Hotels-Vacation-Englewood-Cottage.h66054317.Hotel-Information)

Olde Englewood Village

9.8/10

Exceptional

(61 reviews)

"Very good, great location 👍👍"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

James M.

CA $204

CA $435 total

includes taxes & fees

Apr 1 - Apr 2

[](https://www.expedia.ca/Port-Charlotte-Charlotte-Harbor-Hotels-Vacation-Englewood-Cottage.h66054317.Hotel-Information)

![Sun loungers, beach towels](https://images.trvl-media.com/lodging/34000000/33550000/33549500/33549492/94be059a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/34000000/33550000/33549500/33549492/281d9168.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/34000000/33550000/33549500/33549492/f8e512af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/34000000/33550000/33549500/33549492/30a99456.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### SUNSHINE GETAWAY VACATION RENTALS

[](https://www.expedia.ca/Fort-Myers-Hotels-SUNSHINE-GETAWAY-VACATION-RENTALS.h33549492.Hotel-Information)

Fort Myers

8.4/10

Very good

(139 reviews)

"Easy location to get where we needed. Clean and spacious."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Chris N.

CA $80

CA $357 total

includes taxes & fees

Apr 14 - Apr 15

[](https://www.expedia.ca/Fort-Myers-Hotels-SUNSHINE-GETAWAY-VACATION-RENTALS.h33549492.Hotel-Information)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/34000000/33570000/33565900/33565827/ffe22745.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33570000/33565900/33565827/34f8f1d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/34000000/33570000/33565900/33565827/46fe9de0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/34000000/33570000/33565900/33565827/ef5ad200.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Pet-Friendly / Family-Friendly Waterfront Vacation Rental + Free Boat Dockage!

[](https://www.expedia.ca/Matlacha-Hotels-Pet-Friendly-Family-Friendly-Waterfront-Vacation-Rental-Free-Boat-Dockage.h33565827.Hotel-Information)

Matlacha

9.4/10

Exceptional

(58 reviews)

"Friendly staff and friendly guests. Great location, beautiful dock. Nice size suite. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

DEBBRA

CA $204

CA $255 total

includes taxes & fees

Apr 1 - Apr 2

[](https://www.expedia.ca/Matlacha-Hotels-Pet-Friendly-Family-Friendly-Waterfront-Vacation-Rental-Free-Boat-Dockage.h33565827.Hotel-Information)

![On the beach, beach umbrellas](https://images.trvl-media.com/lodging/24000000/23060000/23058100/23058060/f04917c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/24000000/23060000/23058100/23058060/7974d300.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/24000000/23060000/23058100/23058060/e8be2131.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/24000000/23060000/23058100/23058060/3e71a017.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Gulfside Resort – Silver Sands #241A by RVA

[](https://www.expedia.ca/Sarasota-Hotels-Silver-Sands-241a-Hotel-1-BA-Resort-On-Longboat-Key-By-Rva.h23058060.Hotel-Information)

Longboat Key

8.4/10

Very good

(48 reviews)

"We enjoyed this fun spot with private beach, pool, and more!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Willow C.

CA $222

CA $474 total

includes taxes & fees

Mar 27 - Mar 28

[](https://www.expedia.ca/Sarasota-Hotels-Silver-Sands-241a-Hotel-1-BA-Resort-On-Longboat-Key-By-Rva.h23058060.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/24000000/23090000/23089500/23089447/1524b831.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/24000000/23090000/23089500/23089447/ac586d43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/24000000/23090000/23089500/23089447/54938b93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/24000000/23090000/23089500/23089447/c390520c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Hideaways at Point Pleasant (Palm Side)

[](https://www.expedia.ca/Bradenton-Hotels-The-Hideaways-At-Point-Pleasant-Palm-Side-Downtown-Bradenton.h23089447.Hotel-Information)

Bradenton

10/10

Exceptional

(171 reviews)

"perfect location and size for what we were looking for"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

michael w.

CA $165

CA $356 total

includes taxes & fees

Apr 8 - Apr 9

[](https://www.expedia.ca/Bradenton-Hotels-The-Hideaways-At-Point-Pleasant-Palm-Side-Downtown-Bradenton.h23089447.Hotel-Information)

![Sun loungers, beach towels](https://images.trvl-media.com/lodging/29000000/28880000/28879600/28879579/25aec540.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/29000000/28880000/28879600/28879579/1249367c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/29000000/28880000/28879600/28879579/c65f07e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/29000000/28880000/28879600/28879579/186d8b22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### NEW!! The “WATERSIDE” COTTAGE\~With dockage

[](https://www.expedia.ca/Fort-Myers-Hotels-New-The-Waterside-Cottagewith-Dockage.h28879579.Hotel-Information)

Bokeelia

10/10

Exceptional

(45 reviews)

"We had the best, relaxing time in this adorable waterside cottage. The host is the best!! We loved everything about this vacation spot."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Cheryl H.

CA $240

CA $518 total

includes taxes & fees

Mar 25 - Mar 26

[](https://www.expedia.ca/Fort-Myers-Hotels-New-The-Waterside-Cottagewith-Dockage.h28879579.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/33000000/32650000/32646500/32646464/89e93530.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/33000000/32650000/32646500/32646464/e744663e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, books](https://images.trvl-media.com/lodging/33000000/32650000/32646500/32646464/abdd305f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/33000000/32650000/32646500/32646464/d3975936.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### LAST MINUTE DEALS! FREE WiFi ,Anna Maria Island Just Around The Corner or Stroll to Bay!

[](https://www.expedia.ca/Bradenton-Hotels-Banyan-In-Bradenton.h32646464.Hotel-Information)

Sunny Shores

9.6/10

Exceptional

(37 reviews)

"The property was excellent and close to all of the things needed! Great vacation spot!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Melanie

CA $156

CA $600 total

includes taxes & fees

Apr 15 - Apr 16

[](https://www.expedia.ca/Bradenton-Hotels-Banyan-In-Bradenton.h32646464.Hotel-Information)

![Beach nearby](https://images.trvl-media.com/lodging/38000000/37780000/37773600/37773558/60f75399.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/38000000/37780000/37773600/37773558/d1c97ffa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/38000000/37780000/37773600/37773558/5e89da2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/38000000/37780000/37773600/37773558/1b9fcdf7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Newly remodeled Parrot Nest Toucan Cottage! Walk to beach, shops, restaurants!

[](https://www.expedia.ca/Sanibel-Hotels-Newly-Remodeled-Parrot-Nest-Toucan-Cottage-Walk-To-Beach.h37773558.Hotel-Information)

East End

9.6/10

Exceptional

(48 reviews)

"Great place "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Christine

CA $314

CA $586 total

includes taxes & fees

Apr 14 - Apr 15

[](https://www.expedia.ca/Sanibel-Hotels-Newly-Remodeled-Parrot-Nest-Toucan-Cottage-Walk-To-Beach.h37773558.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/63000000/63000000/62992200/62992152/54820e50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/63000000/63000000/62992200/62992152/59f71aef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/63000000/63000000/62992200/62992152/b18d8140.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, books](https://images.trvl-media.com/lodging/63000000/63000000/62992200/62992152/3d538ac7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Freshly Remodeled Island Suite w/ Pool & Pet Friendly

[](https://www.expedia.ca/Anna-Maria-Hotels-Well-Appointed-Beach-Condo-With-Pool-Access.h62992152.Hotel-Information)

Anna Maria

8.2/10

Very good

(43 reviews)

"Everything about the property was great, especially the location, which is walking distance away from restaurants and island shops."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Ron H.

CA $223

CA $518 total

includes taxes & fees

Mar 26 - Mar 27

[](https://www.expedia.ca/Anna-Maria-Hotels-Well-Appointed-Beach-Condo-With-Pool-Access.h62992152.Hotel-Information)

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.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2026-04-02&endDate=2026-04-03&regionId=6233839&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true)

## Top Southwest Florida Hotel Reviews

![Golden Host Resort - Sarasota](https://images.trvl-media.com/lodging/1000000/30000/21400/21331/6dc32504_y.jpg)

### Golden Host Resort - Sarasota

4/10 Poor

"Checked in very late in the evening and got a room where the AC condenser was extremely loud. Did not sleep at all the first night. Phone line was not operating either and could not report it during that night. Condenser was somewhat fixed the following day. "

[](https://expedia.ca/Sarasota-Hotels-Golden-Host-Resort-Sarasota.h21331.Hotel-Information)

![Naples Grande Beach Resort](https://images.trvl-media.com/lodging/1000000/20000/15900/15898/018506a5_y.jpg)

### Naples Grande Beach Resort

10/10 Excellent

"Friendly staff, updated room"

[](https://expedia.ca/Naples-Hotels-Naples-Grande-Beach-Resort.h15898.Hotel-Information)

![Lani Kai Beachfront Resort](https://images.trvl-media.com/lodging/1000000/440000/438800/438796/9bc89705_y.jpg)

### Lani Kai Beachfront Resort

6/10 Okay

"We enjoyed the location, the room and having a balcony. It was a little rowdier clientele then we are used to lol and there is obviously some work still being done. There was work being done in the room next to us so there was noise during the day and then partiers loud and rowdy at 2 am but overall we had a great trip and we appreciated all the food options that were right on the property. "

[](https://expedia.ca/Fort-Myers-Hotels-Lani-Kai-Beachfront-Resort.h438796.Hotel-Information)

![Compass by Margaritaville Hotel Naples](https://images.trvl-media.com/lodging/1000000/550000/543700/543614/03101902_y.jpg)

### Compass by Margaritaville Hotel Naples

10/10 Excellent

"The outdoor area was very nice, the rooms were very clean and we received a lot of free stuff with the room ."

[](https://expedia.ca/Naples-Hotels-Compass-By-Margaritaville-Naples.h543614.Hotel-Information)

![La Quinta Inn & Suites by Wyndham Naples Downtown](https://images.trvl-media.com/lodging/1000000/30000/24700/24612/3a0774b2_y.jpg)

### La Quinta Inn & Suites by Wyndham Naples Downtown

8/10 Good

"Front desk was friendly and efficient,"

[](https://expedia.ca/Naples-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Naples-Downtown.h24612.Hotel-Information)

![Spark by Hilton Sarasota Siesta Key Gateway](https://images.trvl-media.com/lodging/1000000/30000/26400/26397/18d283d6_y.jpg)

### Spark by Hilton Sarasota Siesta Key Gateway

6/10 Okay

"The bathroom is so tiny. Rooms are ok. For the price we paid should have been much more. Breakfast was just muffins, bagels, yogurt… very few things."

[](https://expedia.ca/Sarasota-Hotels-Best-Western-Plus-Siesta-Key-Gateway.h26397.Hotel-Information)

![Lido Beach Resort](https://images.trvl-media.com/lodging/1000000/40000/34600/34597/d0399e0e_y.jpg)

### Lido Beach Resort

6/10 Okay

"The day was so so. Staff outside at the bar was Great. Staff bring items to the room never happened. For the price rooms not up to standard AC would not run properly "

[](https://expedia.ca/Sarasota-Hotels-Lido-Beach-Resort.h34597.Hotel-Information)

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