Holiday rentals with a hot tub near Cortez Beach

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!.

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.

AMI Cortez Beach Retreat Poolside Resort-stylePool

Resort-style Heated Pool w/ "Views Over the Water" at Beach + Bay Home - duplex upstairs unit • 65 steps to Cortez Beach + 7 miles of white Anna Maria Island sand! • $150,000 new large, heated pool with salt-water, spillover spa, sitting shelf, +built-in umbrellas. • Gulf + Beach + Bay Views inside home + deck • Paddleboard + Kayak • High-speed WiFi • 3 blocks to Bridge Street restaurants/bars/pier/shopping + listen to the Bell Tower Clock ringing each hour – live music! • Ping pong table

Swim. Soak. Play. | Beaches | 5mi 2 IMG | Dine

Welcome to Villa Delfino—where summer days are filled with sunshine, beach adventures, and island exploration. When evening arrives, the villa transforms into a relaxing oasis with ambient lighting, outdoor gathering spaces, and the perfect atmosphere for creating lasting memories. Experience white-glove hospitality with a responsive local team, hands-on management, and detailed pre-arrival inspections. We're available throughout your stay to ensure a seamless, stress-free vacation.

Playa Esmeralda Home! And add a golf cart!

Our beach home rental boasts 5 bedrooms, 5 1/2 bathrooms we Accommodate up to 12 P, hot tub, bar, play area, full kitchen, and an amazing rooftop with ocean views! Located only two blocks from the beach and just one block from restaurants and shops, this vacation rental has everything you need for a relaxing and fun getaway. Whether you're planning a family vacation, a girls' trip, or a reunion with friends, this beach house has plenty of space to accommodate everyone comfortably.

Beachfront • Steps to Sand • Sunset View • Balcony

Just 14 steps from your second-floor beachfront condo, you’re on the powder-soft sands of Anna Maria Island. The bedroom has a plush queen bed, and the living room offers a queen sleeper sofa. Enjoy a full kitchen, cable TV, high-speed Wi-Fi, shared laundry downstairs, and one assigned parking space. Relax on your balcony with sweeping Gulf views and unforgettable sunsets. Perfect for couples or families, this is a true beachfront retreat with sand and sea at your doorstep.

Beach Condo with Quiet, Private Beach

Escape to our serene 2-BR beachfront condo on Longboat Key. This corner unit offers stunning Gulf of Mexico views and sleeps 6. Enjoy direct beach access, a heated pool, and a private patio perfect for sunsets. Located in the quiet Beach Castle Resort, it's the ideal beach vacation rental for families or couples seeking a tranquil getaway. Walk to local restaurants and cafes from your peaceful retreat. A guest-loved home, consistently rated top 5% among Airbnb’s homes.

Casa Bella-5BR/Waterfront/Pool/Spa-9 Min AMI

Beautifully renovated 5 bedroom home. Located 3 minutes from beach access and 9 minutes to Anna Maria Island. A massive waterfront patio with string lights and heated pool and spa encompass this house. Master bedroom with walk-out to spa. Custom double walk-in shower in master suite. Family room with 86" television, decorative fireplace, and 15' ceiling. Roku TV’s in every bedroom. Outdoor propane grill. Beach chairs, umbrella, and cart. We welcome you to Casa Bella.

Private pool, only two blocks .3 miles from beach!

Just two blocks away from the beautiful white sands of Holmes Beach. Restaurants & night life even closer. Swimming pool and spa are inviting for both romantic getaways as well as families. You will have access to the entire beautiful two story townhouse. The property has a shared wall, but all space is private and quiet. The outdoors are separated and private as well. Plenty of parking, sun, & fun. New mattresses, new couch, and other furniture.

Luxury 3/3 Margaritaville Resort

Our luxury 3 BR/ 3 Bath Margaritaville inspired condo features one of the best unobstructed water views of Anna Maria Sound and Tampa Bay in the community. 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.

Seaside Manor! Pool, Spa and Beach Walk!

Seaside Manor by Anna Maria Island Accommodations TPL21-000096, DWE5105083 Welcome to Seaside Manor, a beautifully updated 3-bedroom, 2-bathroom vacation home just a two-minute walk from the sugar-white sands of Bradenton Beach. With a private pool and spa, multiple living spaces, and a location steps from the free island trolley, this home is the perfect spot for families and friends looking for a relaxed Anna Maria Island escape.

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!