Family-friendly holiday rentals in Hudson

Fire pit, Golf Cart, Kayaks, PedalBoat, Fishing!

Welcome to Azalea by the Sea, your perfect vacation escape! Enjoy endless water activities and relaxation right in your own backyard. Highlights You’ll Love: •🛶 Kayaks for exploring the waterways •🌊 Water Mat for fun on the water •🔥 Fire Pit for cozy evenings under the stars •🎯 Cornhole Boards for friendly competition •.🚗 Golf Cart •🌿 5 Minutes to Weeki Wachee River — perfect for kayaking, paddleboarding, or spotting manatees •🎵 Nearby Bars & Restaurants with live entertainment every night!!

Pool, Oceanview, Walk to Beach/Restaurants, Canal

• 3 Bedrooms • 2 Modern Bathrooms (walk-in showers) • 2 Full Kitchens • 2 Living Areas • Private Pool • 80” Smart TV in main living room • 40” Smart TV in secondary unit • Walk to Beach, Restaurants, and Bars in 10min Experience the entire oceanview retreat — combining both units into one expansive 3-bedroom, 2-bath coastal compound. Perfect for extended families, groups, or multi-couple stays who want shared space with built-in privacy. Ocean views from every room across the entire property.

4BR Private Dock, Warm Spring Canal, Kayaks, Canoe

Remodeled Florida home on a warm spring canal with dock and quick access to Gulf of America. Designed by the builder for your weekend retreat, "Camp Therapy" is situated on 2 lots with 100ft of waterfront. Home features hardwood floors, a gourmet kitchen with stainless appliances, custom cabinetry and granite counters. Three balcony views to enjoy abundant wildlife such as dolphins, manatees and marine life. Home has 3 adult kayaks, 2 youth kayaks, 2 stand up paddleboards and 2 canoes for use.

Heated & Screened in Pool/Coffee Bar/Fully Stocked

🏡 Private Pool House with Large Covered & Screened-In Porch Relax and unwind in this inviting private pool home, featuring a large covered and screened-in porch—perfect for enjoying the outdoors without the bugs. 🌊 Heated Pool Take a dip in the private pool, heated year-round with an electric heat pump (weather permitting), offering comfort no matter the season. Whether you're sipping coffee on the porch or enjoying a swim, this cozy retreat is ideal for a peaceful and private getaway.

Hudson Beach waterfront house, boat lift, Tiki Hut

**NO CLEANING or PET FEES** Visit is limited to registered guests. List price is for 1 guest: $25/ea additional guest per day (regardless of overnight) with a 6 person limit. Enjoy beautiful canals & manatees/dolphins from the spacious tiki hut. Put your boat on our lift or rent from marina down the street; launch one or all of our 3 kayaks or bring yours; fish from the dock. Walk to: 3 seafood restaurants with live music, Hudson Beach, Robert J. Strickland Park, Skeleton Key Marina

Oasis Getaway

Relax with the whole family at this peaceful place to stay. Perfect Getaway with amazing sunset views from the upstairs balcony and a floating dock on a canal perfect for kayaking and manatee sight seeing. This canal will also take you straight to the ocean. Very spacious home with a tennis table located on the first floor and a beautiful pool to enjoy! Close to many attractions like Weeki Wachee Springs, Outdoor trails, a Marina, Water Park, Hudson Beach and great seafood restaurants.

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)

Cozy Studio Getaway w/ Beach Essentials

Enjoy an unforgettable stay in our warm and inviting studio, thoughtfully designed to provide the perfect blend of comfort and style. Whether you're here for a relaxing getaway or a work-related visit, this space offers the ideal atmosphere to unwind and feel at ease. Set in a safe and strategically located area, you'll have quick and easy access to a variety of restaurants, shops, highways, hospitals, and more. You’ll find yourself surrounded by peace, privacy, and a sense of home.

The Bohemian Studio: Separate Entry & Fenced Patio

🚨 Unbeatable Deal‼️Serene Countryside Escape. Surrounded by nature & near everything. This cozy studio offers total privacy, separate entrance & self check-in Great location, minutes away from hospitals, restaurants, springs & beaches 30 min from Tampa Bay Area 🌳 2 Acres & Fenced Patio 🍳 Fully Equipped Kitchen & bathroom 💻 High-Speed Internet, ethernet & FREE Netflix 🚗 FREE Parkings Perfect for traveling nurses, visiting family or romantic escapes. The best of both worlds!

Rachel's Place

Hudson is the best kept secret in Florida. This 2/2 is located just 200 yards from the Gulf of Mexico in the beautiful Sea Pines development. This home is nestled next to thousands of acres of wildlife bird sanctuary. There are kayak trails to follow for hours. Redfish, Sea trout and Mangrove snapper are abundant. This beautifully decorated home is well stocked with anything you may need. There are 2 Kayaks, one two person and one single, 2 adult bikes, and fishing equipment.

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.

Florida Breeze

If you are looking to stay in a quite and safe place here in the Sunshine estate, this may be the right place for you. This a gated condo with beautiful sunset offer lot of amenities . Kick back relax enjoy a nice cold beverage while watching the sunset and you might see a some dolphins. This location is 28 miles from honeymoon island ,36 miles from clearwater beach and 15 miles from weeki wachee spring. There is also great restaurants nearby and trail walks.