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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

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

Book Family Tides 7 Nts get 3 FREE~Pool~Beach view

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!

Siesta Sunset Villa

Recently renovated & steps to the beach. Luxurious Beachfront Villa on Siesta Key. Discover the ultimate beachside vacation at our exclusive villa located on the pristine sands of Siesta Key. With breathtaking views of the Gulf of Mexico, this villa offers a perfect blend of luxury, comfort, and convenience. Step out your door onto a private access to the soft, powdery sands of Siesta. Enjoy expansive living spaces with windows that flood the villa with natural light and stunning sunset views.

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

Heated Pool, Hot Tub, Game Room, Steps to Beach!

Welcome to Island Dreams, the ultimate peaceful escape just 4 min walk from Anna Maria Island's stunning beaches. This fully renovated three-bedroom, three-bath beach house features a Zen-inspired backyard oasis, a private cocktail pool, and a game room! Walk to shops, restaurants, and the trolley stop! Island Dreams offers the perfect blend of relaxation, location, and indoor and outdoor fun! NOTE: Holmes Beach has a 7-day rental minimum. Check in / Check out days are on Saturdays.

Modern & Bright Escape: Mins Beach, Pool, Hot Tub!

Relax & un wind in this stylish 1BR, beachfront Siesta Key duplex. Just steps from the sparkling Gulf Coast beaches, this private getaway features colorful interiors, a cozy bedroom, open-plan living & a backyard oasis with a private pool, hot tub & BBQ. Perfect for families, couples, or small groups seeking sun, fun & unforgettable memories. Book now for your dream beach escape! ☀ private pool ☀ Steps To Beach ☀ Life-Size Connect 4 ☀ BBQ Gril ☀ Hot Tub

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.

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. 🌴

NEW! Coconuts 106! Beach Front! Heat Pool!

Welcome to Coconuts Beachfront #106! This renovated ground-floor condo features 1 bedroom and 1 bathroom, on the sands of Holmes Beach. Enjoy Gulf views from the living room, kitchen, and private patio, or step out your back slider straight onto the beach. Perfect for couples or small families, this retreat offers comfort, relaxation, and unforgettable days by the shore.

2B/2BA Penthouse End-Unit Condo

Welcome to 5600 Beach Way #315! A 2 Bed, 2 Bath End Unit Condo with over $175K worth of renovations. The condo is located directly across from the Main Entrance of Siesta Key Beach. With Pickleball Courts and Tennis Courts across the street and the Trolley Stop (easy ride to the Village) in front of your building this is a MUST STAY for your next vacation to Siesta!