Beach house holiday rentals in Longboat Key

5.0 out of 5 average rating, 29 reviews

Home in Bradenton Beach

New! Gulf Views • Rooftop • Bridge St • Game Room!

✨ New Listing 🌅 Welcome to Sunset Beach House on Anna Maria Island! Walk to restaurants, bars, shops, the Pier, and the free island trolley. 🌊 Enjoy Gulf views from two balconies and a rooftop lookout. Just 2 blocks from Bridge Street, this bright and vibrant coastal retreat sleeps 18 with 5 bedrooms and 3 baths. 🎱 A massive game room features a pool table, foosball, poker, ping-pong, bar, and TV lounge. 🌴 With an open layout and endless entertainment, there’s space and fun for everyone!

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An aerial view showcases a spacious outdoor area featuring a private pool and lounge chairs, surrounded by a gated patio. A light blue house stands in the background with multiple windows, providing a connection between indoor and outdoor spaces. Lush greenery lines the property.

4.94 out of 5 average rating, 47 reviews

Luxury 3BD Beachfront Retreat with Heated Pool!

Sandy Bottoms Beach House is a luxury Gulf-front retreat where modern comfort meets Florida’s natural beauty. With three king bedrooms—each with its own en suite bath—this home is designed for families, couples, or groups seeking a premium beach getaway. Step through oversized sliding doors to a private patio with a heated pool, outdoor dining, and a direct trail to the sand. Spend mornings walking the shoreline, afternoons lounging by the pool, and evenings watching unforgettable Gulf sunsets f

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4.97 out of 5 average rating, 39 reviews

Home in Bradenton Beach

Private Pool + Walk 2 blocks to Beach! King Beds!

☀️Welcome to Bayberry Beach Cottage B on Anna Maria Island! Just +/- 400 feet (2 min walk) to the beach! With a Heated private pool, fenced backyard, outdoor games, & grill, it’s the perfect spot for fun-filled days and relaxing nights! 🌴This recently renovated beach cottage has 2 king bedrooms, 1.5 baths. 📍You’re just a 2-minute walk to Salt, a trendy restaurant and craft cocktail bar with live music. More local favorites and beach bars are nearby, & lively Bridge Street is only 1 mile away

LocationFamilyBeach

5.0 out of 5 average rating, 13 reviews

Carissa A | Beachside Retreat | Golf Cart | Pool

Carissa Loft A🏝️ A well-designed home offering comfortable spaces to relax, reconnect & experience all that AMI has to offer! Step inside to discover a private lower level retreat featuring a queen bed, sofa, TV and game table. Upstairs you'll find the fully stocked kitchen, inviting family room, 2-bedrooms & 2-full baths. The private outdoor oasis features a heated/cooled cocktail pool. 🚙Park the car & let the island adventures begin! The 6-person golf cart is complimentary with your stay!

FamilyLocationPool

4.91 out of 5 average rating, 129 reviews

Home in Siesta Key

Siesta Key Escape: Sleeps 10 - Pool - Gated Beach!

Unwind in this spacious 4BR/2BA Siesta Key getaway, set on a quiet street steps from gated, private beach entry. Enjoy a resort-style shared pool when you're not at the shore, then head out to Siesta Key Village restaurants, shops, and the island's top attractions. ✔ 4 Bedrooms (Sleeps 10) ✔ Private Beach Access ✔ Open Design Living ✔ Renovated Chef's Kitchen ✔ Private Patio & Shared Outdoors (Pool, BBQ, Games, Fire Pit, Lounges) ✔ Smart TVs ✔ Wi-Fi ✔ Laundry ✔ Parking Learn more below!

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4.94 out of 5 average rating, 105 reviews

The duplex features a light blue exterior with a welcoming porch adorned with yellow and blue chairs. Lush palm trees and vibrant landscaping enhance the outdoor space, while a clear blue sky adds brightness to the scene. Graveled parking is visible in front of the unit.

Home in Anna Maria

Do you love the beach?

Seaside Sanctuary is the ground floor unit of a beachfront duplex. It is the 2nd house from the beach with no roads to cross. The front yard is thirty steps from one of the most pristine beaches on the Gulf of Mexico. The house is located on a quiet residential street near the north end of the island. The front porch is a great place to watch the sunset. The house is clean, comfortable and well appointed. We welcome well behaved dogs and have a fully fenced yard for your pup to play.

LocationFamilySleep quality

4.98 out of 5 average rating, 125 reviews

Home in Bradenton Beach

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.

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5.0 out of 5 average rating, 11 reviews

NEW! w/ Pool - The Pearl Unit 2 on AMI

The Pearl (Unit 2) is a newly renovated oasis in the heart of Holmes Beach on Anna Maria Island. Just a 3–5 minute walk to the beach, this sunny AMI duplex home has everything — sparkling saltwater pool, fresh interiors, no stairs, beach gear, and parrots that may say hi on your morning walk! Centrally located and steps away from the AMI trolley to whisk you around the island! Relax, explore, and live your best island life. *pool is shared with one other unit in the duplex home*

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An outdoor view showcases a private pool surrounded by lush landscaping and tropical palm trees. The distant beach features soft white sand meeting turquoise waters. A spacious deck, complete with loungers, offers a perfect relaxation spot under clear blue skies.

4.9 out of 5 average rating, 73 reviews

TOES IN THE SAND!

Waves Edge South is one of two very unique homes situated directly on the sugar white sands of Anna Maria Island. Welcome to a dreamy island which oozes the charm of ‘old’ Florida and will remind you of yesteryear when you were young and the pace was a little slower. A place where visitors and residents are as likely to use a bicycle or a golf cart as hop in a car. An Island where the warm waters will soothe your soul and you will leave longing to return once more.

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5.0 out of 5 average rating, 8 reviews

Home in Anna Maria

Beach Baby/4 Min Walk to Beach/ Pool/HotTub /Games

Welcome to Beach Baby – Your Laid-Back Island Escape Just a short stroll from the sugar-white sands, Beach Baby is your perfect Anna Maria Island getaway. Located only six houses from the Gulf and about a 4-minute walk to the stunning Bean Point Beach, this bright and breezy retreat is all about soaking up sunshine, salty air, and easy coastal living. Spend your days beach hopping, biking to local shops, or simply unwinding in your own private backyard oasis.

FamilyAccuracyIndoor spaces

4.94 out of 5 average rating, 133 reviews

A living area is depicted with a neutral color palette and light hardwood flooring. A blue sofa and a wooden coffee table sit in front of a television on a console. A dining area with a table and chairs is visible in the background, alongside large sliding doors leading to an outdoor space.

Home in Siesta Key

Siesta Beach home w/ private access, walk to town!

Welcome to your own private getaway directly on Siesta Beach! Meticulous, updated unit with amazing location to the village and access to tow You will literally, walk out your door, down the steps, and directly onto the beautiful, fine, powdery white sand of Siesta Key Beach. Private Paradise directly on the white powdery sand of Siesta Key! 2 bedroom 3 bathroom beachfront home with Gulf views that sleeps 8.

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