A crowded beach with people sunbathing and swimming.

Historic Hotels & Resorts in Southwest Florida from NZ$298

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Check availability on Southwest Florida Historic Hotels

Tonight
6 Sept - 7 Sept
Tomorrow
7 Sept - 8 Sept
Next weekend
11 Sept - 13 Sept
In two weeks
18 Sept - 20 Sept

Our top choices for Southwest Florida historic hotels

A crowded beach with people sunbathing, swimming, and walking along the shore.
An outdoor patio with a pool, surrounded by palm trees and chairs.
A marina with several boats docked, a bridge in the background, and tall buildings.
A clear swimming pool with lounge chairs and umbrellas, surrounded by palm trees and a building with a balcony.

1. SUNSHINE GETAWAY VACATION RENTALS

SUNSHINE GETAWAY VACATION RENTALS
Fort Myers
United States
SUZANNE M.
NZ$437
includes taxes & fees
25 Sept - 26 Sept
SUNSHINE GETAWAY VACATION RENTALS
A family of four holding hands on a sandy beach with a clear sky and calm sea in the background.
A pathway surrounded by trees and plants, leading to a central area with a bench and a small garden.
A room with a dining table, chairs, a TV, and a sliding glass door leading to an outdoor area with a wooden fence and palm trees.
An outdoor seating area with a table and chairs under a red umbrella, surrounded by greenery.

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

Newly remodeled Parrot Nest Toucan Cottage! Walk to beach, shops, restaurants!
East End
United States
Stephen
NZ$515
includes taxes & fees
8 Sept - 9 Sept
Newly remodeled Parrot Nest Toucan Cottage! Walk to beach, shops, restaurants!
A modern kitchen with a central island, built-in appliances, and a dining area with a round table and chairs.
A bedroom with a bed, bedside table, lamp, artwork, and a TV on the wall.
A two-story house with a balcony, a covered patio, and a view of the surrounding neighborhood.
A modern kitchen with white cabinetry, stainless steel appliances, and a granite countertop.

3. Approx.720 ft to Beach, Pool, Walk to restaurants, Beach Gear, Full Kit, WD, BBQ

Approx.720 ft to Beach, Pool, Walk to restaurants, Beach Gear, Full Kit, WD, BBQ
Fort Myers Beach
United States
Tammy M. A.
NZ$818
includes taxes & fees
8 Sept - 9 Sept
Approx.720 ft to Beach, Pool, Walk to restaurants, Beach Gear, Full Kit, WD, BBQ
A bedroom with a bed, a desk, and a chair. There is a kitchen area with a refrigerator, sink, and cabinets.
A modern kitchen with white cabinets, a dining area with two chairs, and a flat-screen TV mounted above the counter.
Angler's Inn with a colorful facade, a parking area, and palm trees in the background.
A compact kitchen with white cabinets, a stainless steel refrigerator, a sink, and a window with blinds.

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

Pet-Friendly / Family-Friendly Waterfront Vacation Rental + Free Boat Dockage!
Matlacha
United States
Nicolette K.
NZ$298
includes taxes & fees
8 Sept - 9 Sept
Pet-Friendly / Family-Friendly Waterfront Vacation Rental + Free Boat Dockage!
A covered outdoor area with a hammock, wooden deck, and string lights.
A rustic kitchen with wooden cabinets, a central island, and a stone backsplash.
A gravel pathway flanked by wooden fences and illuminated by artificial lighting, leading through a wooded area with trees and plants.
A covered porch with wicker furniture, a small table with a vase of flowers, and a hanging planter.

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

Country Cottage, 40 Acres, Outdoor Kitchen w/ B-que, Campfire, & Horse Stables.
LaBelle
United States
Jacob S.
NZ$435
includes taxes & fees
8 Sept - 9 Sept
Country Cottage, 40 Acres, Outdoor Kitchen w/ B-que, Campfire, & Horse Stables.
A beachside restaurant with a thatched roof, wooden tables, and chairs, overlooking a sandy beach and the ocean.
A kitchen with white cabinets, a stainless steel refrigerator, and a window with blinds.
A kitchen with a stainless steel refrigerator, wooden dining table, and white cabinets.
A marina with several boats docked at wooden piers.

6. LAST MINUTE DEAL, Charming Elevated Duplex – Relaxing Beach Getaway Near Anna Maria Island- Bay access

LAST MINUTE DEAL, Charming Elevated Duplex – Relaxing Beach Getaway Near Anna Maria Island- Bay access
Sunny Shores
United States
Bryce W.
NZ$835
includes taxes & fees
12 Sept - 13 Sept
LAST MINUTE DEAL, Charming Elevated Duplex – Relaxing Beach Getaway Near Anna Maria Island- Bay access
A bedroom with a large bed, a hanging light fixture, a window with curtains, and a door with louvered panels.
A sandy beach with a large sandcastle and a person standing in the background.
A covered deck with a table and chairs, a patio umbrella, and a sliding glass door.
A living room with a sofa, a coffee table, and a dining area with a table and chairs.

7. LAST MINUTE DEALS! FREE WIFI I Banyan – Peaceful 1BR Getaway Near Beaches, Bays & Dining

LAST MINUTE DEALS! FREE WIFI I Banyan – Peaceful 1BR Getaway Near Beaches, Bays & Dining
Sunny Shores
United States
Lisa V.
NZ$661
includes taxes & fees
8 Sept - 9 Sept
LAST MINUTE DEALS! FREE WIFI I Banyan – Peaceful 1BR Getaway Near Beaches, Bays & Dining
A two-story house with a covered porch, a small front yard, and a clear blue sky.
A compact living space with a kitchen, dining area, and a living room featuring a television, sofa, and decorative wall art.
A dining area with a table, chairs, a refrigerator, and a window with curtains.
A covered patio with a ceiling fan, two chairs, a table, and a door with a window.

8. The Hideaways at Point Pleasant (Palm Side)

The Hideaways at Point Pleasant (Palm Side)
Bradenton
United States
Diane M.
NZ$504
includes taxes & fees
8 Sept - 9 Sept
The Hideaways at Point Pleasant (Palm Side)
A beach pathway leading to beach chairs and thatched umbrellas, with a clear view of the ocean.
A beach entrance with a rope barrier, a sign indicating private property, and a building with a thatched roof in the background.
A garden with palm trees, a gravel path, and a post office sign.
A beachside room with a table and chairs, a bottle of wine, and a view of the beach and ocean.

9. Gulf Views - No Stairs - Directly “On the Beach” - Jensen's "On the Gulf" - Cozy Suite 1

Gulf Views - No Stairs - Directly “On the Beach” - Jensen's "On the Gulf" - Cozy Suite 1
Captiva
United States
Bryant
NZ$867
includes taxes & fees
8 Sept - 9 Sept
Gulf Views - No Stairs - Directly “On the Beach” - Jensen's "On the Gulf" - Cozy Suite 1
A wooden pathway leading to a beach with lush greenery and a clear sky.
A resort with a swimming pool, beach, and ocean view.
A pool area with a green building, palm trees, and a clear sky.

10. Silver Sands 1BR – Gulfside Comfort #255 by RVA

Silver Sands 1BR – Gulfside Comfort #255 by RVA
Longboat Key
United States
Anonymous traveller
NZ$640
includes taxes & fees
8 Sept - 9 Sept
Silver Sands 1BR – Gulfside Comfort #255 by RVA
View all properties

Top Southwest Florida Hotel Reviews

Compass by Margaritaville Hotel Naples

Compass by Margaritaville Hotel Naples

10/10 Excellent
"Love the place. Clean, good food and great energy!"
Francinne 3-night trip
Posted 7 hours ago
Compass by Margaritaville Hotel Naples
Pink Shell Beach Resort and Marina

Pink Shell Beach Resort and Marina

10/10 Excellent
"Excelente servicio y atención"
Gina 2-night trip
Posted 8 hours ago
Pink Shell Beach Resort and Marina

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