Vacation rentals with a pool in Cortez

Walk to it all! Restaurants + Heated Pool +Beach!

🌊🏖️Welcome to Making Waves on Anna Maria Island-where you are steps from the beach and centrally located to it all, footsteps to the trolley stop! Escape to paradise and experience the ultimate beach getaway at this stylish beach house with heated pool, nestled in the heart of Anna Maria. Walk outside the door to the pristine beaches, renowned local restaurants, and the vibrant Bridge Street with live music, restaurants, bars, and shopping. Our beach retreat promises an unforgettable vacation!

Family · Location · Walkability

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 · Location · Layout

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

Location · Family · Comfort

Fruit /Botanical Garden Estate 2 ml to downtown EV

Indulge at this Mediterranean estate, boasting lush botanical gardens and rare tropical fruit trees for your picking pleasure. Enjoy the custom pool, hot tub, sauna, cold plunge and the home gym. The expansive outdoor haven features a fully-equipped kitchen, fireplace, TV, and dining space. Enjoy leisurely games of pool, ping pong & shuffleboard, then retreat to the luxurious indoors with comfortable beds and a massive TV, all within the privacy of a walled-in estate. Your lavish escape awaits.

Value · Family · Beach

Steps to the beach! Condo with pool at The Terrace

Just 200 steps from the white sands of Holmes Beach, this beautifully updated 2BR/2BA condo has everything to offer! Our unit features high-speed internet, Keurig , balconies off of each bedroom, 1-car garage, washer/dryer, heated shared pool, and access to all the beach necessities (toys, umbrellas, chairs, tent, bicycles, SUP, cart). This unit sleeps 6 (1-King, 1-Queen, & Full size sofa bed). LOCATION, LOCATION! You'll be just steps from restaurants, cafés, shops, and the free island trolley!

Location · Value · Parking

"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.

Value · Family · Getting around

Canal Retreat: Heated Pool • Dock • Kayaks • Bikes

Wake up to canal views, explore the mangroves on a kayak, and unwind in your private pool after a beach day on Anna Maria Island. Or, explore the neighborhood on bike.Your perfect Gulf Coast getaway starts here! Why you’ll love it: Private dock for fishing and mooring your boat Use of one tandem kayak and two bicycles included for your stay Heated, sparkling screened pool 3 sleep spaces: 2 spacious bedrooms and 1 cozy bunk room Fully stocked kitchen 5 min to shops, dining & IMG Academy

Location · Value · Biking

Sunrise Villa - Tropical 3 bedroom home with pool

Relax with the family at this tropical oasis. Sunrise Villa sits in the corner of a quiet cul-de-sac, just a quarter mile from Palma Sola Bay and 5 miles from the quaint island of Anna Maria and its sandy white beaches. Enjoy the tropical backyard paradise and the abundance of restaurants, beaches, and entertainment in close proximity. Lounge by the pool, take a bike ride along the bay, take a short bike/car ride over to the island, or take a short car ride to downtown Bradenton.

Family · Value · Getting around

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.

Family · Location · Walkability

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 · Location · Cleanliness

New Luxury 3/3 Condo in Margaritaville Resort

Our luxury 3 BR/ 3 Bath Margaritaville inspired condo features wonderful unobstructed water views of Anna Maria Sound and Tampa Bay. The unit features a gourmet kitchen, high-end mattresses, furniture and electronics. The unit comes with bikes and plenty of beach gear. Come enjoy one of the best units in the only luxury development in the area. Skip the hassle of a trip to the off-site management office with keyless entry.

Family · Value · Beach

The Lazy Turtle ~ Canal-Front Retreat

The Lazy Turtle offers bright, spacious indoor and outdoor living spaces with plenty of room for the whole family to unwind! Enjoy the private pool, personal putting green, and peaceful canal-front backyard--perfect for fishing, kayaking, viewing wildlife, or docking your own boat. Located near the sugar-sand beaches of AMI and the charming coastal city, Bradenton, it's the perfect place to relax and enjoy sunny Florida!

Family · Location · Check-in