Family-friendly holiday rentals in Florida

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.

Coastal Escape: Kid-Friendly Pool & Playground

★ Family-friendly Palm Harbor retreat near beautiful beaches - Honeymoon Island: 6 miles away - Clearwater Beach: 15 miles away ★ Heated saltwater pool ★ Screened-in lanai ★ BBQ grill ★ Large fenced backyard with playground ★ Outdoor dining area ★ 3 bedrooms with new mattresses - California king size bed - Queen size bed - Kid-friendly room w/ 2 bunk beds ★ Renovated kitchen and bathrooms ★ Open living space for family gatherings and movie nights ★ Toys, games and kid-friendly extras

LUX Villa w/ Private Salt Water Pool, Lanai, Canal

Are you looking to swim, relax outdoors, fish and take in beautiful sunsets on a wide gulf access canal? If so you will fall in love with this stunning newly constructed custom built home! The 2750 square foot home is bright & airy with two main bedroom on-suites & a separate family wing! The gourmet kitchen, dining room & great room open via large sliders to the lanai & pool w/ views of the canal in much desired SW Cape! Beach inspired villa! Large captains walk & Tiki! Check out our reviews!

Unique Container "Caja Verde" 1 Mile UF & Downtown

Our home is less than a mile to UFHealth at Shands and the Malcom Randall Veterans Medical Center. We are a mile to the University of Florida campus. Amazingly, also a short bike ride (1-2 miles) to Downtown Gainesville. Close to Depot Park, art studios, restaurants, music venues, and theater. Nature parks close too. The bonus is we live on 2 acres, tucked back in a quiet neighborhood. Our pool is deep & cool; we have bikes to borrow. The container is perfect for a solo traveler, or a couple.

TreeHouse, Swings, HotTub, HeatedPool, ClearSpring

Family focused home 6 mins from Weeki Wachee River Park and Buccaneer Bay. 10 minutes to Pine Island Beach. Designed to optimize family time with a custom tree house play area, swing set, play station 4, and game room. Adults can relax in the hot tub, dine al fresco in the screened in pool area while watching TV, use the onsite gym equipment or enjoy the outdoor fire pit or indoor fireplace. Whole house/pool Radio & blue tooth. The entire family will love Pool Heating from Nov and April.

Pileated Place

Welcome to our A-frame cabin, nestled in charming Old Florida Woodlands. It’s complete with two cots, a hinged wall/awning, fire pit, lounge chairs, a hammock, and a picnic table. From this soft pine-needled space, enjoy the view across the pond, go explore the seasonal garden, feed the fish, and meet our farm dogs. Mostly, enjoy ease and reconnection nature encourages. Due to severe drought this year, the pond is currently very low. However, you can still spot koi, bass, and brim. 🙏🏼

Charming Lakefront Log Home

Welcome to your perfect lake retreat! Located on a no public access lake. This charming log home has a private dock and boat ramp suitable for launching your boat for fishing or skiing. There are kayaks on premises for use. This is an ideal location to enjoy North Florida’s lake life with family, friends, or work retreat. Includes a fully stocked kitchen, covered porch, fire pit, gas grill, and WiFi if you feel the need to plug in. NOT suitable for parties or events. NO loud noise, please.

Ozello Keys Cottage on Crystal Bay

2/1 Ozello coastal cottage on stilts surrounded by nature, tranquility, and endless views of the water and estuary. Nature lovers paradise. World renowned fishing and scalloping. Regular dolphin and manatee sightings. Relax with the whole family on the large screened back porch providing gorgeous views of the Nature Coast and stunning sunrises over the salt marsh. The open floor plan opens up to a large screened porch with a dining and lounging space with private and expansive water views.

A lil country, A lil beach time

* Enjoy the lovely setting of this romantic spot in nature, a full acre with a small pond! Only 45 minutes to most beaches. Beautiful country with small antique town and parks to explore. Private acre close to farm. Walk out the door and see farm animals and a lovely pond. 2 loft bedrooms with queen beds. Downstairs has a daybed. Kitchenette complete with fridge sink and cook stove. Outside bar area on one side and the other has a fire pit and hammock. So the WiFi iffy. . plenty of DVD’s!

Ruby Oaks Farm w/ Beach Near St. JohnsRiver

Farm life at its best! Located right next to our tree farm, bass stocked pond with dock on property, decor is Palm trees, Exotic Zebra farm life. There is a Chicken coop to feed chickens and gather eggs (if they are laying). Pasture with miniature Mediterranean donkey, ( Pablo) Zebra. (Ruby ) 1 miniature pygmi goats (Oreo), pig, (Georgia ) and a lamb (Grady ). I am a phone call away! 6 min drive physically. We also have a beautiful venue you can rent for a weddings or an an event.

Screened Lanai /Clear Kayak / Waterfront / Fire Pi

Funky Flamingo River Cottage is a hidden gem on the Weeki Wachee River, designed for fun, relaxation, and adventure. Enjoy a no-see-um screened lanai, a comfy king bed, Smart TVs in every room, and a fully stocked kitchen. Paddle with manatees in our clear kayak, float on the lily pad mat, or unwind by the fire pit. With games inside and out, a hammock, and direct water access, it's the perfect escape—just off the main river, between the State Park and Roger’s Park.

2 BR Luxury Oasis 1 Block from Beach & Downtown

There’s no place like the Cocoa Villa 🌴🏖️ Experience the charm of Cocoa Beach at our Cocoa Villa! Nestled just a block from both the beach and downtown, this modern Spanish-style retreat offers convenience and comfort. With 2 bedrooms, 4 beds, and inviting seating areas, it's your perfect coastal getaway. Explore the town or soak up the sun, then return to your peaceful oasis to relax by the firepit under the stars. Your unforgettable beach trip awaits!