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 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)

Tomorrow

[Mar 21 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=6233839&startDate=2026-03-21&endDate=2026-03-22&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/be06cc75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/72000000/71780000/71773700/71773667/3a1c70aa.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

(82 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 $352 total

includes taxes & fees

Mar 22 - Mar 23

[](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)

![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)

![Smart TV, books](https://images.trvl-media.com/lodging/67000000/66060000/66054400/66054317/edb5b449.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)

![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)

![Outdoor pool](https://images.trvl-media.com/lodging/34000000/33550000/33549500/33549492/571cb420.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 $361 total

includes taxes & fees

Apr 5 - Apr 6

[](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)

![Exterior](https://images.trvl-media.com/lodging/34000000/33570000/33565900/33565827/53827245.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)

![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)

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

![Exterior](https://images.trvl-media.com/lodging/24000000/23060000/23058100/23058060/a4287e66.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)

### 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 $221

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)

![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)

![TV](https://images.trvl-media.com/lodging/24000000/23090000/23089500/23089447/ac586d43.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)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/29000000/28880000/28879600/28879579/c6ccd492.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 $241

CA $519 total

includes taxes & fees

Mar 30 - Mar 31

[](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)

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

![Property grounds](https://images.trvl-media.com/lodging/33000000/32650000/32646500/32646464/98081750.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 $581 total

includes taxes & fees

Apr 11 - Apr 12

[](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)

![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)

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

![Interior](https://images.trvl-media.com/lodging/38000000/37780000/37773600/37773558/b8015c4d.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 $315

CA $588 total

includes taxes & fees

Apr 5 - Apr 6

[](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/63000000/63000000/62992200/62992152/09e81533.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 $218

CA $513 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=2026-04-03&endDate=2026-04-04&regionId=6233839&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true)

## Top Southwest Florida Hotel Reviews

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

### Naples Grande Beach Resort

10/10 Excellent

"Staff was so friendly and acomodating. Rooms, beds and common areas are spacious, bright and comfortable. The beach is gorgeous and magical for collecting shells in the morning. This hotel has been a favorite of ours for years and we look forward to returning."

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

10/10 Excellent

"Everything was great. Great price for the stay in a great location "

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

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

### Lani Kai Beachfront Resort

10/10 Excellent

"Completely finally renovated from Ian, new rooftop area, food was exceptional at graces trattoria and island view. Springbreak was slower but that was fine. Expanded beach area new bars. More mature crowd, roads to and from island less crowded"

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

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

### Golden Host Resort - Sarasota

6/10 Okay

"Uncomfortable seating (i.e. no lounge chair to sit in ). Thought I booked a 'suite' with at least a love seat/lounge chair or other seating to watch TV. Shower was for disabled access, which was fine, but water ran out of the thing into the bathroom and room. Had to figure out how to take a shower and where to put bathmat so that wouldn't happen. Staff was hit/miss as far as being pleasant/helpfull."

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

2/10 Terrible

"The room was small and very smelly. The carpet was sticky when you walk on it continental breakfast nothing to write home about."

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

![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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