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Historic Home Rentals

Step Back in Time: Historic Home Rentals for a Charming Florida Stay

Historic Home Rentals in Florida

If you love the thought of Old Florida like we do you will fall for these historic Florida vacation rentals. Chosen due to their unique historic architecture or interiors. There's something to be said about stepping back to a simpler time. Start your search below.

JANUARY- APRIL 2026 AVAILABLE CLOSE TO SIESTA, PET FRIENDLY/YARD/ POOL/GYM WALK TO BAY&RESTAURANTS
From/Per night$75

JANUARY- APRIL 2026 AVAILABLE CLOSE TO SIESTA, PET FRIENDLY/YARD/ POOL/GYM WALK TO BAY&RESTAURANTS

Sarasota Vacation Rentals
2/BR 2/BA SLEEPS 4
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Islamorada - Oceanfront - Private 1 acre Estate | Heated Pool - 4000 sq.ft | 4 Bed + Den | 5 Bath | Dockage
From/Per night$1607

Islamorada - Oceanfront - Private 1 acre Estate | Heated Pool - 4000 sq.ft | 4 Bed + Den | 5 Bath | Dockage

Islamorada Vacation Rentals
4/BR 5/BA SLEEPS 12
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$ 1 1 0 nt D E A L for Sept 27 till Oct 4th -Beautiful Laguna Beach Cottage Directly Across the Street from the Beach!
From/Per night$119

$ 1 1 0 nt D E A L for Sept 27 till Oct 4th -Beautiful Laguna Beach Cottage Directly Across the Street from the Beach!

Laguna Beach Vacation Rentals
4/BR 2/BA SLEEPS 9
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Take a Fun Trip ! - Only 4 Doors to the Beach! Cute and Clean!
Last Minute!
From/Per night$119

Take a Fun Trip ! - Only 4 Doors to the Beach! Cute and Clean!

Panama City Beach Vacation Rentals
2/BR 1/BA SLEEPS 6
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Islands West 15C by FGC
From/Per night$233

Islands West 15C by FGC

Longboat Key Vacation Rentals
2/BR 2/BA SLEEPS 4
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Naples Paradise Monthly Rental - Steps to Beach!
From/Per night$150

Naples Paradise Monthly Rental - Steps to Beach!

Naples Vacation Rentals
1/BR 1/BA SLEEPS 2
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South Florida Charm - Jupiter Weekly and Monthly Rental
From/Per night$225

South Florida Charm - Jupiter Weekly and Monthly Rental

Jupiter Vacation Rentals
4/BR 2/BA SLEEPS 8
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THE COZZI COTTAGE - Historic 1 Bed 1 Bath Cottage - Anna Maria Island Vacation Rentals
From/Per night$200

THE COZZI COTTAGE - Historic 1 Bed 1 Bath Cottage - Anna Maria Island Vacation Rentals

Holmes Beach Vacation Rentals
1/BR 1/BA SLEEPS 4
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Almost Heaven Vilano Luxury BeachHOUSE- On beach HOUSE
From/Per night$300

Almost Heaven Vilano Luxury BeachHOUSE- On beach HOUSE

St Augustine Vacation Rentals
3/BR 2.5/BA SLEEPS 8
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The Original Sand Dollar: Historic Charm Meet Beach Chic in the Waterfront District
From/Per night$105

The Original Sand Dollar: Historic Charm Meet Beach Chic in the Waterfront District

Gulfport Vacation Rentals
1/BR 1.5/BA SLEEPS 4
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Island's End at Boardwalk, Pensacola Beach Vacation Rental
From/Per night$225

Island's End at Boardwalk, Pensacola Beach Vacation Rental

Pensacola Beach Vacation Rentals
2/BR 2.5/BA SLEEPS 6
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Chasing Sunsets - three houses from the beach
From/Per night$900

Chasing Sunsets - three houses from the beach

Holmes Beach Vacation Rentals
4/BR 3/BA SLEEPS 8
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Dolphin House: Split Floor Plan Charmer with Shaded Yard, Near Waterfront
From/Per night$210

Dolphin House: Split Floor Plan Charmer with Shaded Yard, Near Waterfront

Gulfport Vacation Rentals
3/BR 2/BA SLEEPS 8
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July 2025 Discount! 7 houses from beach! Heated Pool and Hot Tub! 5 Min Walk 2 Natural Beach with no buildings! Wonderful porch and fenced yard yard!
From/Per night$100

July 2025 Discount! 7 houses from beach! Heated Pool and Hot Tub! 5 Min Walk 2 Natural Beach with no buildings! Wonderful porch and fenced yard yard!

Ormond-by-the-Sea Vacation Rentals
2/BR 2/BA SLEEPS 8
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Best Location on St. Teresa Beach
From/Per night$286

Best Location on St. Teresa Beach

St. Teresa Vacation Rentals
4/BR 3/BA SLEEPS 12
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CASA POSADA - So Close to Beach You Hear the Waves! Updated Clean Beach Cottage, Start $180n
From/Per night$180

CASA POSADA - So Close to Beach You Hear the Waves! Updated Clean Beach Cottage, Start $180n

Anna Maria Vacation Rentals
2/BR 1/BA SLEEPS 6
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Caribbean Surf PRIVATE POOL ONLY 3 MINUTE WALK TO BEACH -SLEEPS 6
From/Per night$349

Caribbean Surf PRIVATE POOL ONLY 3 MINUTE WALK TO BEACH -SLEEPS 6

Holmes Beach Vacation Rentals
3/BR 2/BA SLEEPS 6
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Island Garden Villas ~ 6 Private Cottages where Old Florida charm meets refreshing modern luxury
From/Per night$200

Island Garden Villas ~ 6 Private Cottages where Old Florida charm meets refreshing modern luxury

Holmes Beach Vacation Rentals
2/BR 2/BA SLEEPS 6
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Mount Dora, Lake Front Guest House
From/Per night$96

Mount Dora, Lake Front Guest House

Mount Dora Vacation Rentals
2/BR 1.5/BA SLEEPS 4
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Ft. Myers Bliss: Walk to Best Eats & Shops and a Short Drive to Beaches!
From/Per night$165

Ft. Myers Bliss: Walk to Best Eats & Shops and a Short Drive to Beaches!

Fort Myers Vacation Rentals
1/BR 1/BA SLEEPS 2
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Ft. Myers Bliss: Walk to Best Eats & Shops and a Short Drive to the Beach!
From/Per night$165

Ft. Myers Bliss: Walk to Best Eats & Shops and a Short Drive to the Beach!

Fort Myers Vacation Rentals
1/BR 1/BA SLEEPS 2
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Tarpon Springs Florida Hibiscus Garden Apartments @109 Hibiscus Street, Tarpon Springs Fl.
From/Per night$55

Tarpon Springs Florida Hibiscus Garden Apartments @109 Hibiscus Street, Tarpon Springs Fl.

Tarpon Springs Vacation Rentals
1/BR 1/BA SLEEPS 3
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Relaxing 2 BR 1.5 BA Home w/Private Pool & Outdoor Dining - 5 Min Walk to Beach!
From/Per night$150

Relaxing 2 BR 1.5 BA Home w/Private Pool & Outdoor Dining - 5 Min Walk to Beach!

Indian Rocks Beach Vacation Rentals
2/BR 1.5/BA SLEEPS 6
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A Fisherman's Hideaway
From/Per night$288

A Fisherman's Hideaway

Longboat Key Vacation Rentals
2/BR 2/BA SLEEPS 5
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