A crowded beach with people sunbathing and swimming.

Historic Hotels & Resorts in Southwest Florida from NZ$309

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Check availability on Southwest Florida Historic Hotels

Tonight
23 Oct - 24 Oct
Tomorrow
24 Oct - 25 Oct
This weekend
23 Oct - 25 Oct
Next weekend
30 Oct - 1 Nov

Our top choices for Southwest Florida historic hotels

A covered outdoor area with a hammock, wooden deck, and string lights.
A covered porch with wicker furniture, a small table with a vase of flowers, and a hanging planter.
A rustic kitchen with wooden cabinets, a central island, and a dartboard.
A kitchen with wooden cabinets, a granite countertop, a stove, a microwave, and a refrigerator. There are two chairs and a table with a raccoon figurine.

1. 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$474
includes taxes & fees
24 Oct - 25 Oct
Country Cottage, 40 Acres, Outdoor Kitchen w/ B-que, Campfire, & Horse Stables.
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.
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.

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$586
includes taxes & fees
27 Oct - 28 Oct
Newly remodeled Parrot Nest Toucan Cottage! Walk to beach, shops, restaurants!
A crowded beach with people sunbathing and swimming, and a sign indicating no pets, alcohol, or live shelling.
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.
A building with palm trees in front. There are posters on the wall advertising events.

3. SUNSHINE GETAWAY VACATION RENTALS

SUNSHINE GETAWAY VACATION RENTALS
Fort Myers
United States
Immaculate N.
NZ$440
includes taxes & fees
31 Oct - 1 Nov
SUNSHINE GETAWAY VACATION RENTALS
A beach with sun loungers, umbrellas, and a sign indicating no pets, alcohol, lifeguard, or live shelling.
A patio area with a pool, outdoor seating, and palm trees.
A sign for 'The Garden Shoppe' with a white picket fence in the foreground.
A marina with several boats docked, a bridge in the background, and tall buildings.

4. Sunshine Getaway Vacation Rentals!

Sunshine Getaway Vacation Rentals!
Fort Myers
United States
Richard O.
NZ$453
includes taxes & fees
24 Oct - 25 Oct
Sunshine Getaway Vacation Rentals!
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.
A covered patio area with a white chair, a table, and a bench.
A compact kitchen with white cabinets, a stainless steel refrigerator, a sink, and a window with blinds.

5. 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$309
includes taxes & fees
4 Nov - 5 Nov
Pet-Friendly / Family-Friendly Waterfront Vacation Rental + Free Boat Dockage!
A modern kitchen with white cabinets, a dishwasher, and a marble countertop.
A spacious library with bookshelves, a dining area with chairs, and a large potted plant.
Living area
A golf course with multiple water hazards, surrounded by buildings and a beach.

6. Lakeview Resort Condo with Heated Pools & Hot Tubs Near IMG & Anna Maria Island

Lakeview Resort Condo with Heated Pools & Hot Tubs Near IMG & Anna Maria Island
Bradenton
United States
Jane H.
NZ$522
includes taxes & fees
24 Oct - 25 Oct
Lakeview Resort Condo with Heated Pools & Hot Tubs Near IMG & Anna Maria Island
A two-story house with a covered porch, a small front yard, and a clear blue sky.
A covered patio with a ceiling fan, two chairs, a table, and a door with a window.
A living room with a blue sofa, a coffee table, a lamp, a door, and a small cabinet.
A compact living space with a kitchen, dining area, and a living room featuring a television, sofa, and decorative wall art.

7. The Hideaways at Point Pleasant (Palm Side)

The Hideaways at Point Pleasant (Palm Side)
Bradenton
United States
Diane M.
NZ$521
includes taxes & fees
2 Nov - 3 Nov
The Hideaways at Point Pleasant (Palm Side)
A house with a deck, a sliding glass door, and a chair outside.
A dining area with a round table, chairs, and a window with curtains.
A sandy beach with a large sandcastle and a person standing in the background.
A kitchen with green cabinets, a stainless steel dishwasher, a white stove, and a window with a floral curtain.

8. 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$652
includes taxes & fees
26 Oct - 27 Oct
LAST MINUTE DEALS! FREE WIFI I Banyan – Peaceful 1BR Getaway Near Beaches, Bays & Dining
A wooden deck with outdoor furniture, a railing, and potted plants.
A kitchen with white cabinets, a stainless steel refrigerator, and a window with blinds.
A beach with clear water, a sandy shore, and a distant shoreline with buildings.
A kitchen with a stainless steel refrigerator, wooden dining table, and white cabinets.

9. 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$824
includes taxes & fees
1 Nov - 2 Nov
LAST MINUTE DEAL, Charming Elevated Duplex – Relaxing Beach Getaway Near Anna Maria Island- Bay access
A modern kitchen with a central island, built-in appliances, and a dining area with a round table and chairs.
A two-story house with a balcony, a covered patio, and a view of the surrounding neighborhood.
A bedroom with a bed, bedside table, lamp, artwork, and a TV on the wall.
A modern kitchen with white cabinetry, stainless steel appliances, and a granite countertop.

10. 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$744
includes taxes & fees
25 Oct - 26 Oct
Approx.720 ft to Beach, Pool, Walk to restaurants, Beach Gear, Full Kit, WD, BBQ
View all properties

Top Southwest Florida Hotel Reviews

Spark by Hilton Sarasota Siesta Key Gateway

Spark by Hilton Sarasota Siesta Key Gateway

8/10 Good
"The property was nice. It would have been better if the hot tub was in working condition."
Rebecca 2-night trip
Posted 11 hours ago
Spark by Hilton Sarasota Siesta Key Gateway
The Lighthouse Resort Inn & Suites

The Lighthouse Resort Inn & Suites

10/10 Excellent
"Great staff, pools and tiki bars were awesome! Beach was across the street and restaurants were within a 10 minute walk."
Elizabeth 1-night trip
Posted 1 day ago
The Lighthouse Resort Inn & Suites
Pink Shell Beach Resort and Marina

Pink Shell Beach Resort and Marina

10/10 Excellent
"Loved the time there, want to return again!"
Kristin 4-night trip
Posted 2 days ago
Pink Shell Beach Resort and Marina

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