House holiday rentals in Longboat Key

Be an AMI

This stylish and light home offers single-level private accommodations. The recently updated interior and private backyard oasis with plunge pool offers the perfect space for a truly relaxing and enjoyable vacation. Inside, the stylish and comfy space has room for everyone to spread out and relax while enjoying the two flat screen TVs. No expense was spared in designing and furnishing this home. The sleeper sofa pulls out to a memory foam queen bed, meaning the cottage can comfortably sleep 4.

Beautiful Beach House

Beautiful, updated 1937 beach house. Original LongBeach cottage. Gated entrance to property. Three bedroom, two bath. Master bathroom has bathroom en suite. Hardwood floors throughout. Kitchen updated. Beautiful front and back porches to enjoy the sunshine. Private access to beach and Gulf of Mexico. Walking distance to shops and Tennis. Bedrooms include master with King, second bedroom with queen, third bedroom with two twins. Come join us in longboat key for sunshine, beaches,culture,tennis

Summer House longboat key

Luxurious waterfront home with bay and and canal view, new custom kitchen with a view to the pool and your own private tiki bar, dock that can accommodate up to 21 ft boat , whole house just received a complete inside and out make over. Tropical coconut palms, outside patio and grill. Fish on the dock and watch dolphins and manatee. Truly a tropical paradise just 7 minute Walk to your own private beach. minutes from St Armand’s circle. feel free to reach out with any questions or requests

Longboat Key Beach House

This quaint beach house with a private backyard and outdoor shower is everything you need to enjoy your relaxing Florida getaway and includes your beach supplies. It’s only one block to the beach access, convenience store, great restaurants and a deli. Also Included is the use of a membership to Cedars East Tennis Club (5 minute walk), which has Pickleball and Tennis Courts, a junior Olympic POOL, gym, free bicycle rental and tiki bar. Minutes to Holmes, Bradenton and Coquina Beaches.

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.

Salty Harbor AMI pool retreat near the Beach

Charming Salty Harbor sits in a quaint, exclusive corner of AMI and boasts a private heated pool and ample parking for 2 vehicles and even a boat: -Ask us if your dates don't fit our calendar! -If you don't have a single 50Lb pet, please discuss it with us -One of the twin boutique MyAnnaMariaStay homes, look us up! You'll love the luxury mid-century feel, lush yard, and a 6-min walk to the beach, Publix or the trolley stop. AMI was voted a top 50 vacation spot in the world in 2024

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 .

Short walk to beach + Boat dock

The best of island living: a boat dock in back & deeded private access to the white sandy beaches of LBK, just steps down the street. Minutes from Coquina Beach, historic Bridge St. and Anna Maria Island. Sarasota, Lido Beach & St. Armands Circle are a short drive south. A well-stocked convenience store, deli and 3 restaurants (Continental, Italian and Mexican) are a block away; with Euphemia Hay, Lazy Lobster, Dry Dock, Chart House just a short drive.

Relaxing 3BR Retreat+ Hot Tub + Pool +Beaches +IMG

🌴Welcome to Beachway Haven! This 5-Star ⭐️ hideaway is just mins from Anna Maria Island's Pristine Beaches & the Gulf of Mexico. Dive into relaxation with your own Heated Saltwater Pool & Spa Hot Tub, nestled in a tropical oasis. Only a skip away from Golf Courses, Nature Parks, IMG Academy, & Palma Sola Causeway's Beach Access – your gateway to Horseback Riding, Kayaking, & endless sandy adventures. Shopping & dining are only a few mins away too!

Luxe Oasis In St. Armands Circle with Private Pool

🦩 Exclusive Amenities Include: • Private Heated Pool • Walk to St. Armands Circle • Near Lido Key Beach • Entire 4-bedroom, 3-bathroom house. • 1 King Bed, 3 Queen Beds • Regular & Keurig Coffee Maker, Dishwasher, Washer & Dryer, and Kitchen Essentials Provided • Starter Pack of Toiletry & Home Essentials Included - Shampoo, Face Soap, and much more • Beach Towels, Chairs, Cooler, & Caddy Provided • Gas Grill & Fire Table

Beachfront Villa | Pool + Lanai | Hosts 6

Welcome to your private slice of paradise on the coveted Longboat Key. Nestled beachfront, this two-bedroom villa offers barefoot luxury, breezy interiors, and a peaceful atmosphere that instantly slows the pace. Whether you’re here for a family getaway, a quiet reset, or just to listen to the waves with coffee in hand, this sun-drenched retreat delivers serenity in every square inch.

Your DreamOasisAwaits: SiestaKeyEscape with Pool!

Welcome to your dream oasis near the world-famous Siesta Key! ✨ This immaculate 2BD/2BA home is a true coastal gem, offering a serene retreat with stylish design and luxurious amenities. Just 1 mile from the sugar-white sands of Siesta Key Beach, this home provides the perfect blend of comfort and convenience—an ideal spot to embrace relaxed Florida living at its finest. 🌴