Historic Homes in Florida

List View Map View

From $333 /Night

Villa

South West FL > Cape Coral

From $298 /Night

Villa

South West FL > Cape Coral

From $540 /Night

House

Key Largo Area > Anglers Park

Satsang Blue - A Sacred Gathering Place Adorable Bungalow on AMI, Walk to Beach!

Cottage

From $1,650 /Week

Condo

Islamorada Area > Long Key

From $300 /Night

House

Anna Maria Island > Bradenton Beach

From $300 /Night

House

Anna Maria Island > Bradenton Beach

Dock space & pool, beautiful sunsets & park like setting, Center of Islamorada!

House

Islamorada Area > Islamorada

Dock,waterfront,pool,sunsets,Center of Islamorada. Best fishing around

House

Islamorada Area > Islamorada

Dock space,beautiful sunsets & park like setting with pool,Center of Islamorada!

House

Islamorada Area > Islamorada

From $167 /Night

House

South West FL > Cape Coral

From $250 /Night

Condo

Anna Maria Island > Bradenton Beach

From $1,275 /Week

Condo

Anna Maria Island > Holmes Beach

From $375 /Night

House

Northeast FL > Saint Augustine Beach

Direct Oceanfront - Pools, Beach, Private, Clean, Safe

From $275 /Night

Condo

East Central FL > Daytona Beach Shores

The Veranda on Jacaranda - Luxury Home, North Anna Maria Island across from Bean Point

From $350 /Night

House

Anna Maria Island > Anna Maria

Sorrento Vacation Rental in Naples- Vanderbilt Beach

From $580 /Night

House

South West FL > Naples

SMUGGLER'S COVE RESORT - Anna Maria Island Vacation Rentals

From $130 /Night

Condo

Anna Maria Island > Bradenton Beach

White Sands Resort - Weekly - Naples vacation rentals

From $129 /Night

Condo

South West FL > Naples

From $253 /Night

Villa

South West FL > Cape Coral

From $300 /Night

Villa

Anna Maria Island > Holmes Beach

Beachfront -Direct ocean view - Apollo 306

From $199 /Night

Condo

South West FL > Marco Island

Blue Heron Luxury Private Waterfront Oasis on Bimini Bay - Walk to the Beach

From $480 /Night

House

Anna Maria Island > Anna Maria

From $1,195 /Week

Condo

South West FL > Siesta Key

Edge of Paradise at Margaritaville - 5 Night Min

From $170 /Night

Condo

South West FL > Anna Maria Island

From $229 /Night

Condo

South West FL > Siesta Key

Condo

East Central FL > New Smyrna Beach

Meehan - sleeps 6 with heated pool, downtown Port Charlotte from $112nt

From $112 /Night

House

South West FL > Port Charlotte

Beautiful Park Shore Beach on the Gulf of Mexico

From $6,000 /Month

Condo

South West FL > Naples

From $6,000 /Month

Condo

South West FL > Naples

Beach Cottage only steps to the white sandy beaches of Anna Maria Island!

South West FL > Anna Maria Island > Anna Maria

Cottage , Bedroom(s): 2 , Sleeps: 6

Beach Basket is a vintage 1920's cottage located on Oak Ave which dead ends to the white sandy beaches and emerald waters of Anna Maria Island!

ID#: 2069

From $336 /Night

10 Reviews

Luxury Cottage Steps to Bean Point Beach Heated Pool and Outdoor Living Area

South West FL > Anna Maria Island > Anna Maria

Cottage , Bedroom(s): 2 , Sleeps: 4

Seahorse Cottage is located on the desirable North End of Anna Maria with private Heated Pool and Outdoor Living Area

ID#: 2064

From $336 /Night

10 Reviews

North End Cottage -Steps to Beach -Tropical Landscaping Heated Jetted Pool

South West FL > Anna Maria Island > Anna Maria

Cottage , Bedroom(s): 2 , Sleeps: 4

SURF’S UP has been completely and lovingly renovated from top to bottom and is gorgeously decorated!

ID#: 2062

From $317 /Night

11 Reviews

5* FLARBO Award Winner - Historic Florida Cottage 150 yards to private beach 3 bed 3 bath

North West FL > Destin Area > Scenic Gulf Drive Central East

Cottage , Bedroom(s): 3 , Sleeps: 11

3 bed 3 bath clapboard cottage in glorious Frangista Beach Single storey single family home, with glorious south facing front porch.

ID#: 73

From $220 /Night

9 Reviews

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

South West FL > Anna Maria Island > Anna Maria

House , Bedroom(s): 2 , Sleeps: 6

2 Bedroom 1 Bath Beach Cottage, Just 4 Houses to Beach… you can hear the waves!

ID#: 2007

0 Reviews

Waterfront cottage with panoramic views of Tampa Bay

Central West FL > Safety Harbor

House , Bedroom(s): 1 , Sleeps: 2

n/a

ID#: 2120

From $1,295 /Week

6 Reviews

Beautiful beach home in marina neighborhood

Central West FL > Gulfport

House , Bedroom(s): 2 , Sleeps: 6

2 Bedrooms, 1 Bath, Sleeps 6

ID#: 1967

From $90 /Night

2 Reviews

Castaway Cottage + Beach + Heated Private Pool & Spa = R & R! Close to Bean Point!

South West FL > Anna Maria Island > Anna Maria

Cottage , Bedroom(s): 2 , Sleeps: 5

Amazing pool and short stroll to Bean Point. Easy breezy sweet cottage will feel like home away from home! A multitude of money saving amenities! 3 night min.

ID#: 1143

From $280 /Night

20 Reviews

Adorable Bungalow in Gulfport's Marina District - Pet Friendly Fenced Yard

Central West FL > Gulfport

House , Bedroom(s): 2 , Sleeps: 6

1 block to nature park. Private backyard. Deck, shade trees, patio, patio table & chairs, umbrella, tropical landscaping, sm pond, outdoor shower, hammock.

ID#: 498

From $85 /Night

20 Reviews

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

Central West FL > Gulfport

House , Bedroom(s): 3 , Sleeps: 8

3 bedroom/2 bath/2 living area split floor plan home in Gulfport, 2 blocks from O'Maddy's, one block from Beach Boulevard and Art Village Courtyard.

ID#: 352

From $120 /Night

28 Reviews

Two Waves Cottage in Gulfport's Arts District

Central West FL > Gulfport

Cottage , Bedroom(s): 2 , Sleeps: 5

Charming two bedroom cottage just a few blocks from Gulfport Beach

ID#: 1131

From $80 /Night

27 Reviews

Casa de' Coquina Beach House

Northeast FL > Saint Augustine Beach

House , Bedroom(s): 4 , Sleeps: 10

Stunning 4 bedroom home situated on Anastasia Island on St. Augustine's white sandy beaches.This luxury home has quick access to the Anastasia State Beach.

ID#: 1357

From $200 /Night

13 Reviews

Best Location on St. Teresa Beach

North West FL > St. Teresa

House , Bedroom(s): 4 , Sleeps: 12

The Cochran Beach house is located on the site of the first home built on St. Teresa. The water is 100 feet away - right out the front door.

ID#: 1150

From $1,400 /Week

15 Reviews

Vibrant Funky Beach House - St Pete Beach House Monthly Rental

Central West FL > St. Pete Beach

House , Bedroom(s): 1 , Sleeps: 6

Vibrant Funky Beach House for Rent in St Pete's Beach Florida - Sol Jive Beach Hive - Min 30 nights

ID#: 2186

From $120 /Night

0 Reviews

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

Central West FL > Gulfport

House , Bedroom(s): 1 , Sleeps: 4

Charming cottage with wood floors, lots of windows, private patio with lush landscaping, screened sunporch and lots of charm.

ID#: 376

From $78 /Night

25 Reviews

Fish Camp - Efficiency

Central West FL > Gulfport

House , Bedroom(s): 1 , Sleeps: 2

This efficiency apartment contains the same amenities as our larger properties, just on a smaller scale. Perfect for one to two guests.

ID#: 500

From $70 /Night

12 Reviews

Peace River House - "Enjoy the adventure, Embrace the detours."

South West FL > Punta Gorda

Villa , Bedroom(s): 1 , Sleeps: 3

This is a two story attached, but private building with it's own private entrance. Also great for a romantic get-away.

ID#: 490

From $99 /Night

12 Reviews

OFFER

A Touch of Bermuda in Key West

Florida Keys > Key West Area > Key West

Cottage , Bedroom(s): 2 , Sleeps: 6

Cottage, 2 Bedrooms, 2 full Baths, (Sleeps 4-6) with the queen sleeper sofa.

ID#: 805

From $2,000 /Week

15 Reviews

OFFER LAST MINUTE CANCELLATION SPECIAL

Special offer period: Aug 21, 2021 - Aug 28, 2021

Palm Cottage:Vintage Tropical Hideaway in the Waterfront District

Central West FL > Gulfport

House , Bedroom(s): 2 , Sleeps: 4

Just like the town of Gulfport itself, Palm Cottage blends the beloved charm of Old Florida with modern comfort and convenience.

ID#: 497

From $100 /Night

19 Reviews

Historic Gem in the heart of Jupiter Florida

Southeast FL > Jupiter

House , Bedroom(s): 2 , Sleeps: 6

True & timeless peace filled oasis, steeped with history in it's homeyness. Steps from the action of a vibrant town, glorious beaches, golf, boating & parks.

ID#: 2095

From $3,100 /Month

0 Reviews

Gray's Gulf Coast Cottages - Pasadena Estates - starting at $795week - min stays required

Central West FL > St. Petersburg

Bungalow , Bedroom(s): 1 , Sleeps: 4

Enjoy quiet on the red brick roads of Pasadena Estates. Minutes to beaches and attractions. This is a super charming, pet friendly, mid-century bungalow.

ID#: 2244

From $795 /Week

0 Reviews

Introducing Boardwalk Beachhouse: 2BR2BA with Vintage Charm

Central West FL > Treasure Island

House , Bedroom(s): 2 , Sleeps: 5

Perfect for those who looking for more than a place to drop their stuff after a day at the beach. 2 patios, 2 bedrooms, pet-friendly 1,000 feet to the beach!

ID#: 377

From $96 /Night

25 Reviews

Gray's Gulf Coast Cottages - Madeira Beach - starting from $795week - min stays required

Central West FL > Madeira Beach

Cottage , Bedroom(s): 1 , Sleeps: 4

Enjoy the warm sun and beautiful surroundings of Madeira Beach, Florida, from the charming Gulf Coast Cottage that’s just a five-minute walk from the beach.

ID#: 2034

From $795 /Week

0 Reviews

OFFER

A Touch of Cuba in Key West

Florida Keys > Key West Area > Key West

Condo , Bedroom(s): 2 , Sleeps: 4

Unique Large Two Bedroom, One Bath End Unit Condominium

ID#: 863

From $299 /Night

1 Reviews

OFFER SUMMER/FALL2021

Special offer period: Jul 31, 2021 - Oct 16, 2021

Jimmy Buffet Dream Beach House - Heated Pool and Hot Tub. 2 Min Walk 2 Beach.

East Central FL > Ormond-by-the-Sea

House , Bedroom(s): 2 , Sleeps: 8

Love Jimmy Buffet? 7 homes from beach; Heated Pool; Hot Tub; Great Lanai and porch for hangout; Lush backyard landscape; Beach theme and décor; usable garage.

ID#: 698

From $125 /Night

12 Reviews