A sunset over a beach with a pier and people walking on the sand.

Historic Hotels & Resorts in Southwest Coast Florida from NZ$297

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Check availability on Southwest Coast Florida Historic Hotels

Tonight
30 Aug - 31 Aug
Tomorrow
31 Aug - 1 Sept
Next weekend
4 Sept - 6 Sept
In two weeks
11 Sept - 13 Sept

Our top choices for Southwest Coast 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 building with palm trees in front. There are posters on the wall advertising events.

1. SUNSHINE GETAWAY VACATION RENTALS

SUNSHINE GETAWAY VACATION RENTALS
Fort Myers
United States
SUZANNE M.
NZ$440
includes taxes & fees
1 Sept - 2 Sept
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 compact kitchen with white cabinets, a stainless steel refrigerator, a sink, and a window with blinds.
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.

2. 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$297
includes taxes & fees
31 Aug - 1 Sept
Pet-Friendly / Family-Friendly Waterfront Vacation Rental + Free Boat Dockage!
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.
An outdoor seating area with a table and chairs under a red umbrella, surrounded by greenery.
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.

3. 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$508
includes taxes & fees
2 Sept - 3 Sept
Newly remodeled Parrot Nest Toucan Cottage! Walk to beach, shops, restaurants!
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 covered porch with wicker furniture, a small table with a vase of flowers, and a hanging planter.
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.

4. 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$433
includes taxes & fees
31 Aug - 1 Sept
Country Cottage, 40 Acres, Outdoor Kitchen w/ B-que, Campfire, & Horse Stables.
An aerial view of a coastal area with several small islands connected by bridges.
A modern living room with a beige sectional sofa, a round armchair, a glass coffee table, and a striped rug.
A modern kitchen with a central island, wooden cabinets, and a built-in oven.
A nighttime view of a paved pathway flanked by palm trees and a building with illuminated windows.

5. NEW!! The “WATERSIDE” COTTAGE~With dockage

NEW!! The “WATERSIDE” COTTAGE~With dockage
Bokeelia
United States
Jennifer D.
NZ$663
includes taxes & fees
1 Sept - 2 Sept
NEW!! The “WATERSIDE” COTTAGE~With dockage
A modern kitchen with a central island, built-in appliances, and a dining area with a round table and chairs.
A covered outdoor seating area with wicker chairs and a patterned rug.
A modern kitchen with white cabinetry, stainless steel appliances, and a granite countertop.
A bedroom with a bed, bedside table, lamp, artwork, and a TV on the wall.

6. 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$808
includes taxes & fees
31 Aug - 1 Sept
Approx.720 ft to Beach, Pool, Walk to restaurants, Beach Gear, Full Kit, WD, BBQ
A beachside restaurant with a thatched roof, wooden tables, and chairs, overlooking a sandy beach and the ocean.
A kitchen with a stainless steel refrigerator, wooden dining table, and white cabinets.
A beach with clear water, a sandy shore, and a distant shoreline with buildings.
A kitchen with white cabinets, a stainless steel refrigerator, and a window with blinds.

7. 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$819
includes taxes & fees
31 Aug - 1 Sept
LAST MINUTE DEAL, Charming Elevated Duplex – Relaxing Beach Getaway Near Anna Maria Island- Bay access
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 bedroom with a bed, a ceiling fan, a nightstand, and a dresser.
A garden with palm trees, a gravel path, and a post office sign.

8. 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$835
includes taxes & fees
7 Sept - 8 Sept
Gulf Views - No Stairs - Directly “On the Beach” - Jensen's "On the Gulf" - Cozy Suite 1
A beach with a sunset, waves, and two people walking.
A dining area with a round table, chairs, a cabinet, and a painting.
A living room with a sofa, coffee table, bookshelf, and a ceiling fan.
A wooden bench by a dock with boats in the background.

9. 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$657
includes taxes & fees
31 Aug - 1 Sept
LAST MINUTE DEALS! FREE WIFI I Banyan – Peaceful 1BR Getaway Near Beaches, Bays & Dining
A wooden pathway leading to a beach with lush greenery and a clear sky.
An aerial view of a beachfront property with a swimming pool, multiple buildings, and a beach area with umbrellas and lounge chairs.
A resort with a swimming pool, beach, and ocean view.

10. Relax at Gulf – Silver Sands Resort #232, Longboat

Relax at Gulf – Silver Sands Resort #232, Longboat
Longboat Key
United States
Gloria
NZ$594
includes taxes & fees
31 Aug - 1 Sept
Relax at Gulf – Silver Sands Resort #232, Longboat
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Top Southwest Coast Florida Hotel Reviews

Compass by Margaritaville Hotel Naples

Compass by Margaritaville Hotel Naples

10/10 Excellent
"Excelente servicio , amé el lugar"
Jonathan 2-night trip
Posted 7 hours ago
Compass by Margaritaville Hotel Naples
Lido Beach Resort

Lido Beach Resort

10/10 Excellent
"La atención de las personas en el hotel"
Erick 1-night trip
Posted 8 hours ago
Lido Beach Resort
Lani Kai Beachfront Resort

Lani Kai Beachfront Resort

8/10 Good
"I had a wonderful experience…except that both mattresses in our room were sagging; one more than the other. Mine being the one with the largest dip in it. It also made a lot of noise when I moved. Next time I will definitely request a firm mattress!!! Everything else, and I literally mean EVERYTHING, was exceptional! I enjoyed every minute, from the check-in process to the check-out process. I will definitely return!"
Raquel 2-night trip
Posted 12 hours ago
Lani Kai Beachfront Resort
DoubleTree by Hilton Sarasota Bradenton Airport

DoubleTree by Hilton Sarasota Bradenton Airport

10/10 Excellent
"Beautiful hotel with road side parking to watch the planes land and take off. Comfy beds and pillows."
Kristina 1-night trip
Posted 2 days ago
DoubleTree by Hilton Sarasota Bradenton Airport

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