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

2/28-3/13 just became avail SAVE 45%! HURRY!

Let me know if you need a stay for a period not listed. Unbeatable location, HEATED POOL, ultimate makeover & NEW bedrm, bathrm, lounge, & covered patio additions for spacious beauty are a few things that set us apart! Hidden behind our private gate, the beach is just a few steps away & remains uncrowded-even during busiest season. Premium fixtures, appliances, & plush furnishings create elegance. Garage/parking for 6 cars! Near restaurants, Publix, activities! 30 steps to FREE TROLLEY pick up!

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

Beautiful New Home with Ocean View, Steps to Beach

Luxurious 3BR/3BA fully furnished new home that sleeps 11. Enjoy the gorgeous ocean views with two large balconies, perfectly located across the street from the beach, Caddy's restaurant and walking distance to several diverse options, and a 15-min walk to John's Pass (jet skis, fishing, restaurants, and more!) Amenities: - Smart TVs in all rooms - Fully equipped Kitchen - Gas grill - Beach accessories - Board Games - Family friendly

Newly Reno Cozy 1BR w/ Pool - Walk to Gated Beach

Newly renovated gated beach access apartment with a pool. This is a one bedroom and one bath apartment that makes up one unit in a quadplex. It is on a very quiet private road that leads to a gated beach access way that only residents on this street have access too. The house was completely redone and has all new furniture, sheets, pillows, towels, etc. The pool area was just upgraded with new pool/deck furniture.

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.

Perfect Location! Steps to Beach~Heated Pool!

Experience coastal luxury at Villa #2 Shrimp 🌴✨, a stylish studio just a 2-minute walk to Manatee Beach 🌊. Enjoy a king bed 👑, spa-like bath 🚿, kitchenette 🍽️, and a private tropical patio 🌿. Relax by the shared resort-style pool 💦, grill out 🍔, or explore nearby shops and dining 🚎🛍️. Dog friendly 🐾 with approval and includes 1 parking space 🚗—your perfect Anna Maria Island escape awaits!

Ocean Views - Spacious Unit, Bonus Loft & Hot Tub

Welcome to "A Wave From It All" – your perfect retreat on Holmes Beach, Anna Maria Island, FL. Nestled within a charming triplex, our end unit offers front-row views of the Gulf of Mexico, ensuring a truly unforgettable stay. With its unbeatable location, spacious accommodations, and top-notch amenities, this is the perfect escape for families, friends, and couples seeking a memorable AMI getaway.

Waterfront Pool Home Steps to Beach

Escape to our waterfront oasis on Anna Maria Island! This bright, updated home features a private heated pool, hot tub, and dock. Perfect for families, it's just a 5-minute walk to the world-renowned Gulf beaches. Enjoy stunning sunrises, a dedicated workspace, and modern coastal decor. Explore the island with ease via the free trolley. Your perfect getaway awaits!