Beach house holiday rentals in Longboat Key

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

☀️Welcome to Bayberry Beach Cottage A 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

Beautiful ground level with heated pool!

Escape to this cozy cottage on Holmes Beach, just a block from the beautiful shoreline! Perfect for families or couples, this inviting retreat features a comfortable living space and a fully equipped kitchen. Step outside to your private pool, perfect for cooling off after a day at the beach. Enjoy the tropical landscaping and outdoor seating area for relaxation. With the beach so close, you can easily indulge in sunbathing, swimming, and seaside strolls. Experience the charm of island living!

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

New Waterfront Stay • Sauna, Pool & Gym

Escape to a luxury waterfront haven on Anna Maria Island. This elegant retreat blends modern luxury with coastal charm, featuring a canal view with a private boat slip, a heated pool, hot tub, sauna, Gym and private mini-golf. This 4BR/4BA offers two primary bedrooms with ensuite bathrooms. Cook in the fully equipped kitchen or dine al fresco in the outdoor dining area. Just moments from beaches, shops, and dining, this pet-friendly oasis invites pure relaxation and unforgettable memories.

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!

Luxe BeachHouseA/Heated Pool/2 min walk to Beach

Welcome to your home away from home. Sand, sun and ocean breeze are waiting for you. BeachHouse is located 2 minutes walk from the beautiful and quite beach with direct beach access.Its a newly built four story house with nice and private backyard,heated pool,hot tub and beautiful rooftop. We have everything that you need for bigger groups of families to relax on your Beach vacation. BeachHouse is in a quiet neighborhood and walking distance from restaurants, bars and stores. BTR#2099

Gulf Front! Beach Sunsets+ 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.

Luxury 3 Bedroom Beach Home with Game Room!

The perfect beach home DOES exist! Perfectly positioned 2 blocks away from direct beach access, kick up your feet & relax in our cozy 3 bedroom + 2.5 bathrooms with a killer garage space turned game room! While you’re not soaking up the sun on the beach, hang out downstairs and battle it out between air hockey, foosball, giant Jenga & Connect 4 and board games such as Cards Against Humanity. You'll feel right at home in our newly renovated & professionally decorated vacation home!

Trendy & Relaxing: Close to Beach ~ Pool ~ Hot Tub

Discover your perfect Siesta Key getaway in this vibrant 3BR, pet freindly duplex in the peaceful South Village. Just steps from the Gulf Coast beaches, this private retreat blends colorful décor, modern comfort, and playful outdoor fun. Lounge by the private 𝐡𝐞𝐚𝐭𝐞𝐝 𝐩𝐨𝐨𝐥, soak in the 𝐡𝐨𝐭 𝐭𝐮𝐛, or enjoy the backyard murals perfect for families, groups, and beach lovers. Book now for an unforgettable stay! <b>☀ Private Pool ☀ BBQ Grill ☀ Easy Beach Access</b>

High-end Beach heaven, Sleeps 10, 3 private decks

Ideal for those who appreciate single-level living. 3 bedrooms & 2 baths located on the main floor, & loft-style 4th bedroom upstairs. Enjoy 3 decks!: a private beach deck just a 30-second walk away + front & upper decks offering partial ocean views perfect for morning coffee or for cocktails. The primary booking guest must be at least 27 years old, stay on-site during the reservation, and provide valid government-issued ID to host within 24 hrs of booking. Vtr -1609

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.

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. 🌴