Beach house vacation rentals in The Meadows

Location! Beach Access/Trolley/ Restaurants!

📣‼️Location, Location! Welcome to “Island Pearl” 🐚 on Anna Maria Island, where you can leave the car behind! This stylish retreat features a heated pool and is nestled in the heart of the action! 🌴The Trolley Stop is at the end of our block and Bridge Street Pier, a block over. 🏖️Beach access is situated just across the street! Fish from the Bay or catch a sunset while dining at the infamous Beach House Restaurant on Gulf Drive. Many restaurants, bars, and shopping are just a short walk away! 🛍️💃

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

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

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.

AMI Bayfront Paradise, Pool, Kayaks, Bikes & Beach

Welcome to "AMI Paradise on the Bay" Your Luxury Waterfront Escape on Anna Maria Sound, a stunning 4-bedroom, 5.5-bath bayfront retreat designed for relaxation, comfort, and unforgettable memories. Perched along Sarasota Bay with spectacular, sweeping water views, this three-story home offers modern luxury and laid-back island charm. Amenities include Saltwater pool, dock, kayaks, bikes, Game Room with Arcade, Ping Pong, Foos Balls, Elevator and beach supplies. Just blocks to Beach and shops.

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

Luxury Siesta Key Beach Condo Steps from the Sand

🦩Exclusive Amenities Include: • Semi Private Heated Pool • Breathtaking Gulf Views on 3rd & 4th Story Balconies • Less than .7 miles to Siesta Key Village • Less than 20 ft to Siesta Key Beach • 3 Bedrooms, 3 Full Baths • 2 King Beds, 1 Twin Trundle Bed,1 Twin Futon, and 1 Twin Blow Up Mattress (Sleeps 8) • 2 Spacious Balconies w/ Loungers • Private Garage • Regular & Keurig Coffee Maker, Dishwasher, Washer & Dryer, & Kitchen Essentials • Beach Towels, Chairs, Cooler, & Caddy Provided

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.

Gulf Beach Front! Walk to Restaurants + 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.

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! ☀ private pool ☀ BBQ Grill ☀ Easy Beach Access

Beachfront Complex! Heated Pool~Pool View! Updated

Coconuts Unit 102 features a king bed, sleeper sofa, professional linen service, fully stocked kitchen, 75" smart TVs in the living room and bedroom, and a private fenced in poolside patio. Located in a Gulf-front complex with a heated shared pool, BBQ grill, beachfront/poolside loungers, coin laundry, and 1 dedicated parking space—all just steps from the beach! Perfect for a relaxing coastal getaway—just bring your sunscreen and unwind!

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.