Florida Vacation Rentals

Discover vacation rentals throughout Florida

Search All Florida Rentals By Owner 

Start searching thousands of Florida vacation rentals by owner, spanning from the historic charm of St. Augustine to the tropical paradise of the Florida Keys. Our list includes beachfront condos, cozy cottages, and luxurious beach house villas. Located in sought-after destinations like Pensacola, Destin, Panama City Beach, Anna Maria Island, and everywhere in between, your dream Florida getaway awaits. Use the filters and start your search below.

You are currently viewing listings belonging to Once Upon A Beach Vacation Rentals

SANDY PANTS - Designer Beach Chic Home, Steps to Beach, Backyard Oasis w/ Heated Pool

Holmes Beach Vacation Rentals
3/BR 2.5/BA SLEEPS 6

SEA LA VIE - Waterfront Stunning Luxury Home wPool, Spa, Dock, Elevator, Close to Pine

Anna Maria Vacation Rentals
4/BR 4.5/BA SLEEPS 8

COCONUT LAGOON - Lovely Historic Renovated Cottage w/Huge Heated Pool, Backyard Oasis/Cabana/Bar

Anna Maria Vacation Rentals
3/BR 2/BA SLEEPS 6

POINT'S HIDEAWAY - Beautiful Island Home w/ Rooftop Water Views on Bean Point! Pool, Bar, Foosball!

Anna Maria Vacation Rentals
3/BR 3/BA SLEEPS 8

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

On Turtle Time - Beautifully Updated w/Heated Pool, Covered Porches, Walk to Beach!

Anna Maria Vacation Rentals
2/BR 2/BA SLEEPS 6

A WAVE FROM IT ALL - Luxury Renovated Home! Heated Pool, Cabana, Hammock, Walk to Beach

Anna Maria Vacation Rentals
3/BR 3/BA SLEEPS 8

A SHORE THING - Second To None Spacious Waterfront Luxury! Dock, Pool, Spa, Rooftop Water Views!

Anna Maria Vacation Rentals
4/BR 5/BA SLEEPS 10

Casa Mariposa - Luxury Butterfly Garden, Steps to Pine Ave, Pool/Spa, Bikes, 4 Houses to Beach

Anna Maria Vacation Rentals
4/BR 4/BA SLEEPS 8

Catching Waves - Beautifully Updated w/Heated Pool, Covered Porches, Beach Gear, Walk to Beach!

Holmes Beach Vacation Rentals
2/BR 2/BA SLEEPS 6

ISLAND TIME - Island Home w/Enclosed Lagoon Style Pool & Spa, Walk to Beach, Boat Dock, Bikes!

Holmes Beach Vacation Rentals
3/BR 2/BA SLEEPS 6

Shore's Nice - Renovated Pristine Modern Beach Cottage w/ Peek-A-Boo Bay Views

Anna Maria Vacation Rentals
2/BR 2/BA SLEEPS 4

TERN KEY - Pristine Spacious Luxury Canal Home with Pool, Spa, Dock, Bikes, Close to Beach!

Anna Maria Vacation Rentals
4/BR 4.5/BA SLEEPS 8

DECKED OUT - Stunning Luxury Home! Huge Sunny Private Pool, Block to Pine 8 Min Walk to Beach

Anna Maria Vacation Rentals
2/BR 2/BA SLEEPS 4

Mariner's Crossing - Stunning Luxury Home w/ Gulf Views From Every Room, Rooftop Deck, & Pool/Spa

Holmes Beach Vacation Rentals
8/BR 7.5/BA SLEEPS 18

BATEMAN'S - Luxury Canal Front Home with Pool, Spa, Dock, Close to Bean Point & Pine Ave

Anna Maria Vacation Rentals
4/BR 4/BA SLEEPS 8

LA Buena Vida - Bright Beachy & Canal front! Steps to Beach, Pool/Spa, Dock, Dogs OK

Anna Maria Vacation Rentals
3/BR 3/BA SLEEPS 8

SUNSET MARGARITA - Luxury Condo, Pool, Beach Gear, Bikes, Just 5 Mins to Anna Maria Gulf Beaches!

Bradenton Vacation Rentals
2/BR 2/BA SLEEPS 5

Island Girl West - Heated Pool, Covered Porches, Beach Gear, Walk to Beach!

Holmes Beach Vacation Rentals
2/BR 2/BA SLEEPS 6

THREE LITTLE BIRDS - NEW Premier Luxury Home with Stunning Gulf Beach Views, Pool/Spa, High End Home!

Anna Maria Vacation Rentals
4/BR 3.5/BA SLEEPS 8

AcquaLuxe - Exquisite 2022 Lux Canal Home w/ Outdoor Oasis Pool, Spa, Dock, SUP, Kayaks, Fire Pit

Anna Maria Vacation Rentals
4/BR 4/BA SLEEPS 8

Serenity Now - Newly Listed Holmes Beach Beauty. Heated Pool with Sun Shelf

Holmes Beach Vacation Rentals
4/BR 3.5/BA SLEEPS 8

THE COTTAGE ON PINE - Adorable Renovated Cottage w/Private Heated Pool, On Main Street of Anna Maria

Anna Maria Vacation Rentals
2/BR 1/BA SLEEPS 4

Island Girl East - Island Retreat with Private Pool, Shaded Verandas, Stroll to the Beach!

Holmes Beach Vacation Rentals
2/BR 2/BA SLEEPS 6

Florida Rentals

Depending on the location vacation rentals in Florida may be minimum stay restrictions and preferred turnover days. 

  • Hosts in off the beaten path locations often rent homes for nightly stays
  • Nightly rentals can be found more readily in the low season throughout Florida
  • Some hosts in busier cities may require 7 night min stays with check in's on Fridays or Saturdays.
  • Monthly and seasonal rentals can be found in cities that are restricted to 28 night stays.
  • Check information further below to help narrow down your search.

Popular Florida Rentals Searches

Click on the option below for a quick search navigation for Florida vacation rental by owner rentals.


Where to Search for Monthly and Seasonal Florida Rentals?

Discover the perfect escape with our monthly and seasonal Florida rental locations, offering flexibility and comfort for extended stays. From the laid-back beaches of the Gulf Coast to the vibrant cities of Naples and the Florida Keys, we offer a diverse portfolio of properties spanning across the Sunshine State, catering to every preference and lifestyle. Whether you're seeking a winter retreat to soak up the sun or a summer getaway to explore the cultural delights of Florida's cities, our rental locations provide the ideal home base for your extended stay. With options ranging from beachfront condos and cozy cottages to spacious villas and urban apartments, you can immerse yourself in the beauty and excitement of Florida for as long as you desire.

Popular Monthly and Seasonal Locations

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