Holiday rentals with outdoor seating in Florida

New Waterfront Bungalow Retreat + Tropical Vibes

"The River Oak Bungalow" is a brand new 4BR/2.5BA exotic, lush, private estate nestled amongst winding oaks & palms directly on the Indian River Lagoon. Located in the Downtown Eau Gallie Arts District, only a short drive to the Beaches, FIT, USSSA, & MLB Airport. Bring your boat & enjoy a private 100' dock & riverfront sandbar recreation area, huge outdoor deck, spacious backyard, fire pit, tree climbs, paddle boards, and kayaks. Perfect for Family Gatherings, Celebrations, or a staycation!

Luxury Waterfront - private dock, beach, dolphins

Welcome to Casamigos! Spectacular sunrises and sunsets await as you enjoy endless water views from the the privacy of your bedroom or your sixty foot patio, 300 foot dock and almost every interior room. Paddleboard, fish or swim with dolphins, manatees, pelicans and jumping fish from your private beach (on the Indian River-not the ocean) as you relax at your peaceful and luxurious private oasis in paradise. Super fast WIFI if you need to work during your stay! Disabled accessible. Gas grill.

The Palm Tree Getaway

Ever stayed the night in the woods? Cross it off the bucket list with our ‘tiny-house’ style stay near the Hillsborough State Park. Rated #7 on PureWow as one of the 20 Best Airbnb Cabins. This brand new luxury tiny home was thoughtfully crafted to capture the natural beauty of its old Florida virgin forest surroundings. Glamping at its finest with the best modern conveniences like a full gourmet kitchen, spa like shower, 1G FiberWi-Fi Internet, TV, and a super quiet Mini SplitAC & Heating.

The Cocoa Boho Rooftop Retreat

Thinking about your next vacation? Need to unwind? Want to take in ocean views while sipping mimosas on a rooftop patio? Say hello to Cocoa Boho. Brand-new, clean boho-chic with bright & open interiors, a year-round summer breeze and the sounds of the Atlantic. Cocoa Boho is a newly constructed guest home - 2min walk to public beach access, 1.5 miles away from Downtown. If you're booking your next girls trip, poolside retreat or theme park crowd beach escape, Cocoa Boho is that vibe.

Beautiful Beachfront Cottage on the Water

Renovated, romantic 1937 beach front cottage. Last of its kind in the quiet family setting of Indian Shores Florida, halfway between Clearwater Beach and Treasure Island/John's Pass. Truly an "Old Florida" experience with original pine floors, Florida room and covered porches, as well as updated kitchen and bathroom. This house, uniquely built near ground level, allows it to be waterfront on the beach while shaded by huge pine trees. You won't find a more tranquil setting on the beach.

HORSE FARM Retreat, Newer Built Private Guesthouse

Escape to our private guesthouse located in our peaceful but lively 7-acre farm with our family of horses, ponies, Guinea hens, ducks, roosters, chickens, bunnies, cats, & very lovable dogs. Enjoy grabbing fresh eggs, giving animals treats, puppies belly rubs, grilling, making s’mores at the fire pit, and enjoying the farm life! PLEASE read entire listing if little ones will be joining :-) NOTE: Our horses are not available for riding (see our guidebook for great alternate options)

The Little Treehouse 2 at Country Club of Orlando

With rustic urban charm, The Little Treehouse "2" is a perfect relaxation spot for your stay in the City Beautiful. This completely renovated 1926 carriage house downstairs unit is a 260 sq. ft. blend of cosmopolitan comfort and enchantment. Located 5 minutes from Downtown, Amway Arena, Camping World Stadium, 15 minutes to Universal Studios, 25 minutes to Disney and an hours drive to Florida's beautiful beaches! *Search "Little Tree House Orlando" in your browser for more info.

Extraordinary location, private, beach path, cozy

Location, privacy, ocean. Due to health concerns, pool seen from aerial shots not available Nov-May because owners will be in residence in the main house. Welcome to Nova Beach Cottage, the guest house on the oceanfront estate of famous sculptor, Mihai Popa, a.k.a. “Nova”. Located on the south tip of North Hutchinson Island directly next to the Fort Pierce Inlet State Park. Garden and beach path a few steps from the cottage. Screened patio from bedroom.

Cozy A-Frame Retreat w/ hot tub!

Escape to our cozy A-frame cabin, nestled amidst the serene beauty of nature. Just 10 mins from Santos Trailhead and 35 from Rainbow Springs! After a day of exploration, unwind in the private hot tub, gather around the bonfire pit for s'mores, or snuggle by the fireplace and stream your favorite movie. Whether you seek a romantic retreat or an extended family getaway, our A-frame cabin promises the perfect blend of nature's tranquility and modern comfort!