Holiday rentals with a patio near Anna Maria Island Beach

Flamingo Royale — Beach Luxury Resort

Welcome to the Flamingo Royale — Your luxury sanctuary! This exquisite escape gives tropical elegance perfect for indulgent relaxation and unforgettable memories. Experience the charm of old Florida with a modern twist in a stylish setting. Step outside to your personal paradise—a shimmering pool surrounded by lush landscaping & palms galore. W/ beautiful Anna Maria Island just moments away, relish pristine beaches, boutique shopping, and fine dining. Experience paradise at the Flamingo Royale!

Bayfront Beach access with Heated Pool!

Our modern yet beachy retreat is the perfect oasis on the North end of Anna Maria Island w/breathtaking panoramic views of Tampa Bay & the iconic Skyway Bridge. The backyard oasis features a refreshing saltwater pool & fully fenced backyard, complete w/artificial turf & outdoor shower. Just steps away, you'll find full access to a stunning white sandy beach & the crystal-clear waters of Tampa Bay! Conveniences have been carefully considered, creating the most ideal vacation destination!

Bradenton Beach Sunsets 3, Anna Maria Island, FL

Fully furnished water view beach cottage located on beautiful Anna Maria Island across the street from white sand beach and Gulf of Mexico. 1 Bedroom 1 bath unit that sleeps 4 with a queen pull out couch make this a great location for, solo guest, business travelers, and families. . Beach chairs/umbrellas/etc. provided. 3 blocks from historic Bridge Street with lively restaurants and bars. Free island trolley and across the bridge from Cortez fishing village. Free off-street parking.

Spring is in the air - HTD Pool*Hot Tub*Game RM

Elevated Hospitality, Thoughtfully Delivered Experience true white-glove hospitality. Our dedicated team responds within minutes, with hands-on management and a quality inspector ensuring every detail is thoughtfully prepared before you arrive. Throughout your stay, we remain available and attentive to any need—so you can relax and enjoy a seamless, comfortable experience. Welcome to Villa Delfino—your sunny island escape with spring breezes, perfect temperatures, and endless sunshine.

Manatee Sanctuary - in the heart of Anna Maria

Welcome to Manatee Sanctuary – a spacious 3 bed/ 2 bath canal-front retreat with a private heated pool and hot tub, located in the quiet and highly sought-after North End of the island. This serene and private oasis offers everything you need for a relaxed and memorable beach vacation. The home features an open-concept living and dining area, fully stocked kitchen, and an upstairs porch ideal for morning coffee or evening relaxation. The backyard opens onto a peaceful saltwater canal.

Gulf Front! Beach Views!+ 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.

NEW!~ Beach Front/Heated Pool! Coconuts 107

Gulf-front getaway with unbeatable beach access—step out your back door and right onto the sand! Enjoy a king bed, queen sleeper, fully stocked kitchen, in-unit washer/dryer, and professional linen service. Beach towels, two chairs, and an umbrella are included. Relax or grill by the shared heated pool and soak in the stunning Gulf views. Everything you need for the perfect beach escape—just bring your sunscreen and unwind!Relax with the whole family at this peaceful place to stay.

Anna Maria retreat house

Elevated home with all the amenities. Walking distance to the beach, chairs and towels provided. Relax in the backyard patio, including pool with waterfall . The shaded balcony overlooks the pool if you need to escape the sunshine. There’s a free trolley that runs all day in AMI if you don’t want to take the car out. The house is located across the street from Bimini Bay, enjoy a jog through these side streets in the morning. Local shops and restaurants that will not disappoint .

Romantic Quiet Luxury Tiny Home W/ Private Hot Tub

Escape to a tropical paradise in this brand new luxury tiny home, nestled among palm trees. Relax in the private hot tub. Just 6 miles to Anna Maria. Ideal for a romantic getaway or a peaceful retreat. We are located in a quiet neighborhood with a 10PM noise ordinance. If you want a quiet relaxing getaway, our tiny home is perfect for you. A car is recommended in this area as there is limited public transportation. The best rental car rates can be found at TPA/SRQ airport.

Pergola Oasis | Walk to Beach + Outdoor Living

Welcome to Salty Palm, a newly remodeled coastal retreat in the heart of Holmes Beach. Just a short walk to the white sandy beaches of Anna Maria Island, this home features a private covered pergola with outdoor lounge seating and dining, creating the perfect space to relax day or night. Steps from shops and eateries, with nearby bike and golf cart rentals, plus access to community amenities including a boat ramp, kayak launch, fishing dock, and tennis & pickleball courts.

KING Bed + Anna Maria Island Beaches + Beach Gear!

⚓️🦩Welcome to the Coastal Flamingo! Your nautical getaway that combines style, fun, and the serene beauty of the Gulf Coast. This cozy, vibrant themed condo is the perfect destination for your next Beach vacation. Walking distance to Palma Sola Beach Causeway, where you can enjoy sun-bathing, horseback riding, jet skiing, and fishing! 5 mins or less from the Gulf of Mexico and powdery white sand beaches of Anna Maria Island! Kick back and relax in this coastal escape!

Cozy Cottage - POOL HOME! 3/3

A Cozy Cottage is the ultimate retreat for relaxation and reconnecting with family and friends. Each bedroom offers direct access to the pool area. The kitchen is abundantly stocked! The spacious Living Room with adjoining Dining Area provides a sleeper sofa. Quietly located on the northern end, but easy walking distance to Anna Maria's Historic 'Pine Ave'. Lush tropical landscaping and a spacious entertaining area surround the private heated pool.