Family-friendly holiday rentals in Cortez

Cottage w/ Pickleball Outdoor Oasis 2 mi to Beach

Immerse in fun at the charming Cortez Cottage in Bradenton! Enjoy close proximity to the beach and seafood restaurants, plus an outdoor oasis with a heated pool, hot tub, BBQ grill, fire pit, 65" outdoor TV, pickleball, ping pong, and cornhole. Clean and fully equipped, our 3-bedroom home sleeps 11. Praised for our cleanliness and hospitality, we have all you need for an unforgettable family vacation. Join our delighted guests: book your stay at Cortez Cottage, where the beach meets family fun!.

Family · Indoor spaces · Sleep quality

Gorgeous bay view, 2/2 house, boat ramp & dock

Beautiful, fully updated & spacious 2 bedroom, 2 ba unit. Peaceful & safe. 2 mi. to Bradenton Beach/Anna Maria Island, easy to drive or bike. Enjoy gorgeous views of Sarasota Bay! Waterfront just steps from house. Fish off dock, watch dolphin and manatee, plus sunsets on the bay. We have a deeded boat ramp and dock with truck and trailer parking. Great for fishing, kayaking, jet skis, boat trips to Jewfish & Longboat, AMI, etc. Separate attached studio apartment available to rent as well

Family · Quiet · Nearby

Coastal Luxe Villa! Near AMI

Welcome to Coastal Luxe Villa, your perfect Florida escape—nestled in historic Cortez and just minutes from the sandy shores of Anna Maria Island. This spacious three-level coastal retreat combines modern comfort with beach-town charm, offering stunning bay views and endless amenities for unforgettable memories. Private garage with a bonus table tennis setup Sparkling heated saltwater pool with outdoor seating, dining, firepit table, and gas grill Convenient elevator access to all three floors

Kitchen · Family · Nearby

Cortez Lighthouse Cottage / Entire Cottage

Entire Lighthouse Cottage 2 Bedroom 2 Bath, Full Kitchen with LOTS OF EXTRAS. Very Tropical , Spacious & Relaxing . Historical Cortez Fishing Village 1 1/2 miles away. 2 Miles From Gulf Of Mexico, Beautiful Beaches, 🏖🏝Shopping, Restaurants, Golf, Fishing, Boating, Jet Ski, Fishing Charters, Dolphin Sight Seeing Tours & Much More. Come Join The Fun In The Sun (WE DO REQUIRE A $75.00 PET FEE . LIMIT 2 PETS ) HUGE FIELD FOR KIDS & PETS TO RUN & PLAY.

Kitchen · Family · Amenities

Ty's Canal Cottage

"Welcome to Ty's Cottage in Historic Cortez Fishing Village, which is one of Florida's last working fishing villages. Located within walking distance to well known Starfish, Swordfish, Tide Tables Restaurants and Tyler's Homemade ice cream. A short 1.3 mile walk to Anna Maria Island with gorgeous beaches. Short driving distance to beautiful golf courses such as IMG Academy Golf and Manatee County Golf Course. Local fishing charters for outstanding fishing. Outdoor sitting area on canal."

Family · Kitchen · Accuracy

"Manatee" 3 miles to Anna Marie

Heated, Shared Pool! More affordable & away from the congestion at Anna Maria Island & still close enough to drive (Only 3 miles). Lots of Restaurants & Shopping Nearby. The Manatee Duplex offers 2 Full Baths, 2 Bedrooms, A Large Sofa Sleeper, Full/Twin Bunkbed/Daybed in the Florida Room. Comfortably Sleeps 6-8 People. Big Fenced in Private Backyard, Patio, Table, Chairs, Umbrella, Sun Loungers, Gas Grill, Beach Accessories to take to the Nearby Beaches. Plenty of Parking for a Boat/Trailer.

Family · Indoor spaces · Shared spaces

Gulf Front! Sunset Deck! + Walk to Bridge St Pier!

🌊🏄Welcome to The Surof House - where panoramic views of the Gulf of Mexico welcome you from almost every corner! 🏖️Experience the ultimate beachfront retreat at this unique & stunning property nestled across from one of the top beaches in the world. A perfect blend of luxury, comfort, & unparalleled views awaites. With an upstairs loft featuring 3 single beds & 2 downstairs rooms with king beds, it's an ideal getaway for families, friends, or anyone seeking a slice of paradise.

Kitchen · Indoor spaces · Parks

Cortez ~ Grouper Cottage. BRING YOUR BOAT!

This waterfront home with a private dock and boat slip is the perfect place to get away. Grouper Cottage is an ideal cozy place to unwind and enjoy sunsets and dolphins. You will fall in love with this refurbished historic cottage—set in a private, tranquil setting, with picturesque palm trees and mangroves surrounding the property's shoreline. Cortez dockside cottages is nestled on an acre with a compromise of old Florida with the historical background a laid back Island vibe.

Kitchen · Family · Beach

3BR/3BA + Waterfront! Hot tub + Pool + Beaches!

🌊🌴Welcome to Kingston’s Hideaway, a beautiful waterfront oasis just 2 miles from the pristine Gulf beaches of Anna Maria Island! Whether you're seeking relaxation, adventure, or a bit of both, this home offers a tranquil and luxurious escape for your next vacation! Waterfront Canal: Direct access for boating and paddleboarding-(1 paddle board available for use) Private Dock: Conveniently dock your boat right at the house (27 ft max) Pool & Hot Tub: Relax and rejuvenate.

Indoor spaces · Kitchen · Sleep quality

Rustic Coastal Escape| Pool | Fire Pit

Welcome to Rustic Coastal Escape, a charming 3-bedroom, 2-bath retreat inspired by relaxed beach living and vintage coastal style nestled in historic Cortez village. Thoughtfully decorated with rustic touches and coastal décor throughout, this home offers a warm, inviting atmosphere perfect for families, couples, and friends looking to unwind near Florida’s Gulf Coast. The beach is just a 2 minute drive or just a 15 to 20 minute walk away.

Family · Indoor spaces · Walkability

Dockside Dreams - Pool, Spa & Waterfront Dock

Welcome to Dockside Dreams - Your Waterfront Paradise! Escape to our home nestled along the serene waters, less then 3 miles from Bradenton Beach. This is not just a vacation; its an aquatic adventure waiting for you! - Private Boat Dock - Dolphin and Manatee Sighting! - Close to the Beach! - Fully Equipped Kitchen - Outdoor Oasis: Soak up the sun on your deck or cook out by the water! Stays of 28+ Days welcome on request!

Indoor spaces · Family · Barbecue

Big Backyard Pool Retreat Near IMG Academy, Beach

Escape to your own private Old Florida oasis where swaying palms, a heated pool wrapped by a freshwater stream, and an outdoor kitchen with TV set the scene for an unforgettable group getaway. Fire pit evenings, beach days with gear provided, and a fully fenced backyard make this the ideal base for families and groups. Pet and toddler friendly. Seven minutes to IMG Academy and ten minutes to Anna Maria Island beaches.

Kitchen · Indoor spaces · Getting around