BEST VACATION RENTALS IN FLORIDA – 2020 FLARBO AWARDSPhoto From floridarentalbyowners

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This is it the FlaRBO Vacation Rental Awards of 2020!

It’s time for some good news! Florida offers some of the most outstanding vacation rentals throughout the world. The bar is set high to offer guests an exceptional experience in their home away from home in the sunshine state. Whether the Florida house rental is located on beachfront, with waterfront views, pet-friendly, long term, or short term we hand-pick the top finalists and showcase this incredible selection of the top FLARBO vacation rentals awards for 2020.

The year 2020 offers a range of options and diversity for any vacation group from little tiny bungalows to mammoth luxury homes that showcase magazine-worthy spaces. We dove deep into over a thousand rentals and looked at a variety of details and factors with many different ranges in price, location, size, and truly unique amenities. We hope you find what you are looking for with our FLARBO 2020 Vacation Rental Award Winners.

Click on any photo or Award Title to locate these rentals. Take note of the listing ID numbers…. then book a fabulous vacay at of these amazing Florida vacation rentals.

Florida Rental By Owners Vacation Rental Listing 2011

Best Coastal Style Living Room – Anna Maria

Sea Glass on Park is a new luxury 4 bedroom beach house with a pool found in Anna Maria, Florida. This home had us swooning over its gorgeous coastal living room area. We love the ocean-inspired rug and throw pillows that instantly transport you to island living. The antique oars are a nod to the nautical flavor of this fabulous home for rent. The rest of the home will have you ready to dive into coastal luxury too!

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Florida Rental By Owners Vacation Rental Listing 1458

Best Beachfront Pool – Spanish Key

Wake up to this view every day in the northwest region of Florida. Spanish Key on Perdido Key is perfect for those who appreciate trendsetting architecture, fine detail, and classic style. This incredible condo boasts three bedrooms, three full baths, and wonderful views from your large balcony overlooking the incredible beachfront pool. Thoughtful furnishings with a beach theme are found throughout the vacation rental and bring the cool blue water and sugar-white sand colors in. You’ll know that you’ve found your “forever” vacation spot!

Florida Rental By Owners Vacation Rental Listing 911

Best in Luxury Class – Destin

This incredible Destin Florida luxury vacation rental blows our minds. Starting at $1,000 per night we think this is well worth the price of admittance. Sink into incredibly sumptuous rooms with high-end kitchen, multiple game room areas, the outdoor cabana area is a true paradise in and of itself. Enjoy the home surround system while entertaining. This home sleeps up to 36 people making it affordable within reach at just $28 per person per night if you have a large crew. Perfect for large groups and wedding parties and only a few steps to the nearby beaches. Simply stunning!

Florida Rental By Owners Vacation Rental Listing 411

Best Beachfront Budget-Friendly in Luxury Class – Perdido Key

There is no wonder that this gorgeous Perdido Key beachfront condo rental was showcased on HGTV’s popular show “Beachfront Bargain Hunt”. Perdido Dream offers incredible luxury and space at a bargain price starting about $100 per night. Enjoy million-dollar views from your relaxing balcony with a good book and glass of wine. At days end sink into the luxurious furnishings that are drool-worthy! Book this Perdido Key rental during high season and enjoy beach chair service. Just one of the perks in this amazing FLARBO condo.

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Florida Rental By Owners Listing 2010

Best Spa and Sun Deck – Anna Maria Island

This lovely Anna Maria Island 4 bedroom property offers an incredible pool & spa which boasts an in-pool table, two large sun shelves, spa spillover, and water features. Perfect for adult cocktails and conversations. The large sundeck area with lounge chairs and umbrella doubles as a docking area alongside the deepwater canal. For the avid boaters… this canal is deep enough to accommodate even large boats.

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Florida Rental By Owners Listing 1996

Best Dive Bar – Marathon

The KeyZ Life is a beautiful 5 bedroom waterfront Marathon, Florida vacation rental with the funkiest dive bar! We love the cool Florida flavor that this outdoor easy-breezy bar evokes in us. Vibrant, juicy, and fun it would be an epic place to watch the big game on the large outdoor TV right from the pool. This vacation rental is a boat-friendly property with 60 feet of dock offering a fish cleaning station. Location on the Gulf of Mexico near the cutaway to the Atlantic ocean.

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Florida Rental By Owners Listing 1999

Best Tropical Design – Holmes Beach

Chic on the Beach is our award for tropical design. We love the seamless design plan of the sandy tones in the furnishings, floor, and backsplash mixed with wood elements and the bright and fun tropical green palm fronds in the bar stools and decorative pillows. The separation of spaces in this duplex allows for the luxury living feeling that vacation rental guests crave. To finish it off the sparkling gold light fixtures complete the look. Sink into this space for less at FLARBO.

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Florida Rental By Owners Vacation Rental Listing

Best Waterfront Gated Community – Naples

Tropical Paradise is found at this upscale, beautifully designed, new gated community in Naples Reserve is close to the white sandy beaches of Marco Island and Naples. In this gated community you’ll enjoy the fabulous zero-entry pool, sip a cool drink at the tiki bar, or join friends on the white sandy beach right at the complex. Enjoy the bonfire pit and the volleyball nets located on the community beach. The 125-acre lake replete with a private island is available for boating or hit the tennis or pickleball courts for some fun. The fitness center is a great way to stay in shape. You’ll never leave the vacation lifestyle right at your doorstep.

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Florida Rental By Owners Listing 1980

Closest to the Beach – Anna Maria

Pirate’s Bay is a vintage seaside beach home that has all the updated conveniences and modern amenities while still keeping true to its laid back beach vibe. Inside, the fully equipped kitchen, living and dining areas are laid out in an open floor plan with a full wall of floor to ceiling windows. Step out your back door and paddle the coastline or sit back with a book, a drink, and a view. This beachside bungalow has all you need to create great vacation memories. A nighttime dip in the pool, looking out at the moonlight on the bay, with the Skyway Bridge lit up in the distance is a quiet pleasure not to be missed.

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Florida Rental By Owners Vacation Rental Listing 1463

Best View – Sunny Isles Beach

Enjoy million dollar incredible views serving the perfect backdrop to your oceanfront vacation condo located in la Perla overlooking the gorgeous Sunny Isles Beach in Southeast Florida. Relax on the oversized wraparound balcony with azure southeast beach and city views. You can even see the pier! Enjoy all that this resort-style condo has to offer including the oceanfront pool. This vacation rental is decorated by a designer and only available for seasonal snowbird rentals.

FLARBO vacation rental award blue and white coastal beach cottage on Cape San Blas Florida

Florida Rental By Owners Vacation Rental Listing 1168

Best Island Beach House – Cape San Blas

Check out the interiors of this Classic Coastal Cape San Blas vacation rental perfect for family getaways on a pet-friendly island. This beach house belongs in magazines with it’s up to the minute coastal living design. The expansive outdoor decks (5) are fabulous spaces to enjoy stress-free moments. We love the thoughtful touches and organic textures found throughout the cottage that make it look like a show home. Sleeping up to 10 people comfortably. It even offers an elevator if needed. You have to see it to believe it!

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Florida Rental By Owners Vacation Rental Listing 854

Best Private Pool and Spa – Cape Coral

We love this custom-designed waterfront Florida villa. A self-proclaimed modern mansion, equipped with high-end technology. The spa amenities are out of this world. Inside enjoy the steam bath, light, aroma, and sound therapy as well as a shower with rain and waterfall options. The pool features a black pebble surface with a jacuzzi hot tub. The outdoor pool system is a saltwater system that is great for sensitive skin. The outdoor fire pits are symbols of water and fire. Swing lazily on the hammock for two while gazing at the stars. Pure heaven!

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Florida Rental By Owners Vacation Rental Listing 1952

Best Retro Backyard – Anna Maria

Naut 2 Shabby Cottage is a three-bedroom 1922 Old-Florida-style beach house for rent in Anna Maria. We were charmed by funky eclectic decor that reminded us of the ’60s. The backyard was made for fun in the sun! The heated pool boasts a basketball hoop, and the hot tub is nestled next to gorgeous tropical landscaping. The soft turf surrounding the pool takes us back to a funkier relaxed time. The juicy tropical colored Adirondack chairs, loungers, and outdoor dining table with umbrella give you everything you need for a cool vibe vacation!

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Florida Rental By Owners Vacation Rental Listing 1790

Best Historic Old Florida Cottage – Lido Key

Rent this award-winning 1924 Historic John Ringling Estate home listed on the National Historic Registry. What a chance to stay in an Original John Ringling Estate home for your vacation! The beautiful Spanish/Mediterranean architecture is stunning and perfectly situated close to shopping, dining, the beach, the bay, and downtown Sarasota. Walk to the best that St. Armand’s Circle and Lido Key have to offer. The large privacy gate guards the tropical courtyard and beautiful pool area. This property is found in the exclusive neighborhood of John Ringling Estates where you can enjoy the space and privacy needed when you want it, while also having the location and proximity to the beach, Sarasota Bay, and lively atmosphere of St. Armand’s Circle.

Florida Rental By Owners Vacation Rental Listing 1133

Best Luxury Townhouse Rental – South Walton Beach

This South Walton Beach rental oozes with luxury hospitality. We love the soft grays, blues, and wood tones found throughout this home. The sparkling chandeliers dripping with crystals and beads speak to the attention to detail taken by the designer. The community of Prominence is the hottest new community on 30-A located near Alys and Rosemary Beach. The “Hub” located across the street features food trucks, restaurants, shops, and an abundance of entertainment. Complimentary beach shuttle service runs during high season. This home sleeps up to 8 people and prices start around $150 per night.

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Florida Rental By Owners Vacation Rental Listing 1201

Best Luxury Beachfront Rental for Large Groups – Destin

Step out the patio door and view the white powder sands, swaying lazy sea oats and sweeping views of the shimmering turquoise waters in the serene Old Florida neighborhood of Gulf Pines, just 5 minutes east of Destin. This home has 8 bedrooms and sleeps up to 26 people. Rates start around $699 per night.

Styled in elegant grandeur, this three level luxury beachfront retreat comprises over 4000 square feet with 8 bedrooms and 6 baths sleeping 26 comfortably on a private beach! Watch the dolphins or fall asleep listening to the waves from any of the 3 levels and travertine decks. Absolute heaven!

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Florida Rental By Owners Vacation Rental Listing 1749

Best Private Island Rental – Marathon

Enjoy your own tropical island in a quiet cove of protected mangroves in the Florida Keys! You can rent this two-bedroom, air-conditioned houseboat that is docked on the island. You have your own 17-foot center console boat for the entire week! A boater’s delight. This is what “Glamping” is all about complete with a refrigerator and clean water! The crystal clear waters around the island are visited by a variety of wildlife including dolphins, manatees, stingray, lobster, crab, octopus, barracuda, parrot, and angelfish, to name a few. Enjoy hours of snorkeling and fishing.

Vacation Rental Awards 2020 - Listing 1085

Florida Rental By Owners Vacation Rental Listing 1085

Best Outdoor Tiki Hut – Oakland Park, FL

The minute you step into this lush tropical garden and pool oasis in this 3-bedroom Oakland Park vacation home you’ll feel like you’re in an exclusive boutique hotel. Enjoy the beautiful Florida sunshine and breezy warm nights in your very own secluded oasis. Beautifully abounds in the landscaped garden the sparkling blue heated pool and spa, tiki hut, outdoor grill, dining table, and plenty of outdoor seating & loungy conversation areas. This home close to Fort Lauderdale sleeps up to 6 people and prices start from $309 per night.

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Florida Rental By Owners Vacation Rental Listing 1321

Most Popular Florida Rental – Bradenton Beach

With over 40,300 views to this Bradenton Beach condo, it’s currently the most popular home on Florida Rental By Owners. The ultimate Sunshine State retreat awaits you at this charming condo found on the Gulf of Mexico. Featuring two-bedrooms and 2 baths, this waterfront home base comfortably accommodates up to 6 guests. Pack the sunscreen and get ready for a memorable stay with family or friends. Look forward to spending relaxing days on the beach or lounging by the community pool. Get out on the water with a boat rental, paddleboard or kayak before venturing out for excellent shopping and dining!

Florida Rental By Owners Vacation Rental Listing 1340

Best Arcade – Panama City Beach

The Beach Retreat is a 7 bedroom coastal beach house that sleeps up to 26 people. Located in the coveted 30A area, this family home boasts family entertainment such as the iconic arcade room. Replete with no less than 5 electronic arcade games to relive your youth. Every TV has movie channels for everyone’s taste. An easy walk over to the beach nearby makes it an ideal family property for reunions and special moments. It’s a great option for large groups yet located in the quiet and private area of Seacrest – 30A.

Florida Rental By Owners Vacation Rental Listing 1403

Best Spa Resort Condo – Miami Beach

Known as Florida’s premier health and wellness destination, the Carillon condo-hotel in Miami Beach are known for their pampering of guests. Condo-hotel guests receive access to more than 300 exercise classes per week. Choose from a wide variety of options including yoga, Reformer Pilates, cycling, ballet, Latin dance, boot camp, HIIT, boxing, belly dance, rock climbing, and more. Each of the four expansive fitness studios offers stunning ocean views and high-end workout equipment. Perfect for fitness-minded travelers. Relax and refresh in utter opulence in this 1 bedroom FLARBO condo which sleeps up to 2 guests.

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Florida Rental By Owners Vacation Rental Listing 1324

Best Kid Themed Bedroom – Kissimmee

This kid-friendly Kissimmee vacation rental oozes with fun. From Star Wars to Rapunzels castle fit for any princess to the Pirates of the Caribbean. Not to be missed are Cinderella, Belle, Moana and Sleeping Beauty bedrooms as well as Harry Potter’s school dorm room. The family 3D home theater room is awesome. Kids can play video games or dress up in their favorite character’s costumes. This 8 bedroom pool home that sleeps 26 is truly epic!

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Florida Rental By Owners Vacation Rental Listing 1553

Best Outdoor Vibes – Anna Maria Island

Escape to your private coastal vibe backyard retreat for a dip in your sparkling heated pool or grab a cool cocktail at the outdoor bar! We love the cute and cool vibe-y atmosphere created by the homeowners. We can think of nothing better than preparing the catch of the day on the grill and dining alfresco under the island night sky. Jimmy buffet couldn’t ask for more! This pet-friendly 3 bedroom home sleeps up to 6 and rents from $265 per night.

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Florida Rental By Owners Vacation Rental Listing 2005

Best Lighthouse Vacation Rental – Anna Maria Island

We love, love, love this Americana Lighthouse vacation rental! It is a truly unique architectural beauty. The red, white, and blue theme continues indoors and out. We think this would be the best spot to celebrate Independence Day. A beacon of outstanding design the lighthouse home has a rooftop viewing deck with astounding 360-degree views. You can experience patriotic living as the “keepers” of The Lighthouse. This landmark home sleeps up to 6 and starts from around $200 per night.

Check out More Amazing Vacation Rentals on FLARBO

These Best Vacation Rentals in Florida vacation rentals are all found on Florida Rental By Owners – FLARBO. There is something for everyone whether you are looking for a beachfront condo for two, a large home for multi-generations, or a snowbird monthly getaway. Vacation rentals are a unique and safe choice for an idyllic and stress-free holiday.

Book one of the best vacation rentals in Florida with your family or friends group. Flarbo – Florida Rental By Owners website is your best bet where you “Book the Same Vacation Rentals for Less”. There are no booking fees for either traveler or owner on FLARBO keeping it simple by booking direct.


Interested in visiting Florida?

You can view all Florida vacation rental properties here. Take advantage of booking directly with the owner which always gets you the best price. Don’t wait to reserve these award-winning Florida vacation rentals they book quickly!

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