Historic Hotels & Resorts in Southwest Florida

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Check availability on Southwest Florida Historic Hotels

Best Southwest Florida Historic Hotels

Crystal Bay Historic Hotel
Relax by the pool surrounded by palm trees and lounge chairs on a spacious deck.

Crystal Bay Historic Hotel

3.0 star property
9.6 out of 10, Exceptional, (1367)
"Great place would definitely stay there again "
The price is NZ$229
includes taxes & fees
19 Aug - 20 Aug
Crystal Bay Historic Hotel
The Don CeSar
Relax by the oceanfront pool surrounded by palm trees and lounge chairs.

The Don CeSar

4.0 star property
9.0 out of 10, Wonderful, (1008)
"Great stay !"
The Don CeSar
Cordova Inn
Classic hotel with a central entrance, adorned with columns and arches.

Cordova Inn

2.5 star property
8.0 out of 10, Very good, (1004)
"Tiny bathroom - you might hit your head on the sink trying to wipe. Shower had less water pressurre than my 90 y/o grandpa trying to take a leak. Got a $55 ticket trying to drop off my luggage!! "
The price is NZ$191
includes taxes & fees
9 Sept - 10 Sept
Cordova Inn
Newly remodeled Parrot Nest Toucan Cottage! Walk to beach, shops, restaurants!
Stroll through lush gardens surrounded by tropical plants and palm trees.

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

9.6 out of 10, Exceptional, (45)
"Great place "
The price is NZ$442
includes taxes & fees
11 Aug - 12 Aug
Newly remodeled Parrot Nest Toucan Cottage! Walk to beach, shops, restaurants!
Country Cottage, 40 Acres, Outdoor Kitchen w/ B-que, Campfire, & Horse Stables.
Relax in a serene outdoor space with a hammock and wooden table under a rustic pavilion.

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

9.8 out of 10, Exceptional, (75)
"Exactly "
The price is NZ$489
includes taxes & fees
10 Aug - 11 Aug
Country Cottage, 40 Acres, Outdoor Kitchen w/ B-que, Campfire, & Horse Stables.
Extremely comfortable&clean VILLAS! Heated pool and Jacuzzi SUMMER SPECIAL RATES
Relax on the beach with lounge chairs and umbrellas scattered across the sand.

Extremely comfortable&clean VILLAS! Heated pool and Jacuzzi SUMMER SPECIAL RATES

9.6 out of 10, Exceptional, (35)
"Looking forward to staying there again."
The price is NZ$740
includes taxes & fees
10 Aug - 11 Aug
Extremely comfortable&clean VILLAS! Heated pool and Jacuzzi SUMMER SPECIAL RATES
LAST MINUTE DEAL, Charming 2 Bed/2 Bath, FREE WiFi, Anna Maria Island Is Just...
Relax on the beach with a meal or a moment of tranquility at this beachside dining area.

LAST MINUTE DEAL, Charming 2 Bed/2 Bath, FREE WiFi, Anna Maria Island Is Just...

9.4 out of 10, Exceptional, (35)
"Excellent for a family trip."
The price is NZ$822
includes taxes & fees
8 Sept - 9 Sept
LAST MINUTE DEAL, Charming 2 Bed/2 Bath, FREE WiFi, Anna Maria Island Is Just...
Historically Significant, 2nd floor, 1 BR, 1 Private BA Close to Everything
Walk along the boardwalk to the wide, open beach.

Historically Significant, 2nd floor, 1 BR, 1 Private BA Close to Everything

9.2 out of 10, Wonderful, (13)
"Cute place .. excellent food"
The price is NZ$299
includes taxes & fees
19 Aug - 20 Aug
Historically Significant, 2nd floor, 1 BR, 1 Private BA Close to Everything
NEW!! The “WATERSIDE” COTTAGE~With dockage
Enjoy a refreshing swim in our pool, surrounded by lounge chairs and umbrellas.

NEW!! The “WATERSIDE” COTTAGE~With dockage

10.0 out of 10, Exceptional, (41)
"My wife and I loved our stay at Waterside. The property was clean and well appointed. The area was nice and we loved walking up to the local watering hole for sunset views. I would recommend it highly. "
The price is NZ$657
includes taxes & fees
11 Aug - 12 Aug
NEW!! The “WATERSIDE” COTTAGE~With dockage
Pet-Friendly / Family-Friendly Waterfront Vacation Rental + Free Boat Dockage!
Relax in a vibrant outdoor space with a glass ceiling, surrounded by lush greenery and a colorful chair.

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

9.4 out of 10, Exceptional, (45)
"This is a cute, clean, comfortable property. The host was super helpful and friendly. We loved it and will definitely be coming back."
The price is NZ$261
includes taxes & fees
11 Aug - 12 Aug
Pet-Friendly / Family-Friendly Waterfront Vacation Rental + Free Boat Dockage!
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.

Top Southwest Florida Hotel Reviews

Hilton Naples

Hilton Naples

10/10 Excellent
"Very clean and great staff. I was extremely happy with my booking."
Casey 3-night trip
Posted 6 hours ago
Hilton Naples