It’s never too late (or early!) to start planning a vacay to the land of sunshine and sand. Here are the best rentals from Key West to Captiva.
When it comes to beach vacations, a spot in the Sunshine State is just about always a good idea. From luxe estates that sleep 30 to a tiny house that's just right for a couples' escape, these vacation spots are on our editors' Florida getaway wishlist.
Crowd Pleaser, Captiva Island
Price available upon request; seaoatscaptivaisland.com
This luxurious 30-sleeper estate (pictured above) is what vacation dreams are made of. Nestled on 4 acres of waterfront, Sea Oats offers guests the comfort of a secluded home along with amenities akin to a five-star resort. In addition to the oversized heated pool, private beach, tennis and basketball courts, bayside dock, kayaks and paddleboards, guests have the option to book a private chef, fishing and boating charters, spa services, and shell tours with a Florida Master Naturalist (and Captiva Island, neighbor to Sanibel, is a shell seeker’s paradise). Sure, you might never want to leave – but, hey, you can always come back.
Related: The Best Shelling Beaches in America
High Note, Key West
From $200 per night; tripadvisor.com
Talk about location. Tucked on a tiny side street between Key West arteries Duval and Simonton, this pine-clad cottage is neighbor to both nightlife and Casa Antigua, Ernest Hemingway’s historic first home on the island. The second-floor studio –dubbed the Rose Treehouse – is elegantly furnished in classic Key West style, with two spacious balconies flanking the home. Toast Papa with a classic daiquiri from the tree-shrouded deck, then pop around on foot or bike to the lively island’s famed attractions. (Here are 15 of our favorite things to do!)
Luxe Hideaway, Delray Beach
From $400 per night; tripadvisor.com
Post up in this elegant estate for a week (or two!) to experience the best of South Florida. Located on the Boca Raton-Delray Beach border, the Intracoastal home is close enough to cruise down to Ft. Lauderdale or West Palm Beach for a night on the town. The five-bedroom retreat is elegantly appointed with modern décor, a chef’s kitchen, pool, and expansive outdoor living space.
Art Deco Dream, Miami Beach
From $1,866 per night; vrbo.com
South Beach is known for its retro Art Deco architecture, and right in the heart of that historic district lies this impressive rooftop penthouse. Two floors of luxurious interiors open up to 3,000 square feet of outdoor space, with a rooftop plunge pool, fire pit, loads of cozy seating and 360-degree views of the Atlantic and Miami's glitzy Ocean Drive. Life has never been lived so fabulously.
Lookover Dunes, Seagrove Beach
From $499 per night; invitedhome.com
Seagrove Beach is just one of a string of pearls along Florida’s scenic Highway 30A, but it’s arguably the area’s unsung gem. Shaded by a thick grove of salt-sprayed oak trees, the mile-and-a-half stretch of beachfront is known as the quiet counterpoint to many of its more bustling neighbors. This oceanfront five-bedroom jewel fits right in. Elegantly understated with serene views of the Gulf from its two levels of balconies, the home is just private enough for kicking back and savoring the silence (or the sound of the waves, of course). Bonus: A private pool and beds for 14 make this a perfect spot for multiple families.
Related: Perfect Weekend on Florida's 30A:
A-Plus Escape, St. Augustine
From $200 per night; vrbo.com
Just two miles north of downtown St. Augustine on the sparkling Atlantic, this quaint A-frame cottage comes with private beach access, a private deck, full kitchen, and picture-perfect views of the sunrise from your elevated loft bedroom.
Private Paradise, Summerland Key
From $775 per night; airbnb.com
While most people could only name a handful or two of the Florida Keys, the archipelago actually consists of approximately 1,700 islands – and one of them could be yours for a weekend. Melody Key is located about a mile from Summerland Key and just a few miles from Key West. This solar-powered home accommodates eight, with its own pool and large balconies for gazing at the crystal-clear aqua sea.
Surf Shack, Anna Maria Island
From $179 per night; airbnb.com
You can love this Holmes Island (just south of Anna Maria) escape for its stones-throw proximity to the beach (25 yards!), or you can love it for its California-meets-Caribbean surf-hippie vibe. Adorably decorated with oh-so-coastal pops of color, the one-bedroom boutique cottage accommodates four guests, and includes access to a private patio and laundry shed.
Old Florida Getaway, Palm Beach
From $125 per night; airbnb.com
Experience this ritzy barrier island from a top-floor condo that epitomizes Old Florida style. Set inside the 1920s-built Palm Beach Hotel, the 550-square-foot retreat is just a block from the beach, with pecky cypress ceilings and a spectacular view of the Breakers (and a very lovable price tag!).
Entertainer’s Paradise, Destin
From $200 per night; tripadvisor.com
Grab your friends and head to this luxurious 20-sleeper getaway in the heart of Destin. With prime views of the sugar-white sand and turquoise Gulf, the three-story home boasts a wide-open great room, gourmet kitchen, and access to the Destin Pointe community amenities, which includes two pools, tennis courts, a seasonal beach trolley, and 3,000 feet of secluded beach access.