Historic Homes in Florida

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!
From $336 /Night
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
From $336 /Night
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!
From $317 /Night
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.
From $220 /Night
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!
Waterfront cottage with panoramic views of Tampa Bay
Central West FL > Safety Harbor
House , Bedroom(s): 1 , Sleeps: 2
n/a
From $1,295 /Week
Beautiful beach home in marina neighborhood
Central West FL > Gulfport
House , Bedroom(s): 2 , Sleeps: 6
2 Bedrooms, 1 Bath, Sleeps 6
From $90 /Night
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.
From $280 /Night
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.
From $85 /Night
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.
From $120 /Night
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
From $80 /Night
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.
From $200 /Night
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.
From $1,400 /Week
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
From $120 /Night
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.
From $78 /Night
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.
From $70 /Night
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.
From $99 /Night
A Touch of Bermuda in Key West
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.
From $2,000 /Week

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.
From $100 /Night
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.
From $3,100 /Month
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.
From $795 /Week
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!
From $96 /Night
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.
From $795 /Week
A Touch of Cuba in Key West
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
From $299 /Night

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.
From $125 /Night