Beach house holiday rentals in Sarasota

Walk to it all! Restaurants + Heated Pool +Beach!

🌊🏖️Welcome to Making Waves on Anna Maria Island-where you are steps from the beach and centrally located to it all, footsteps to the trolley stop! Escape to paradise and experience the ultimate beach getaway at this stylish beach house with heated pool, nestled in the heart of Anna Maria. Walk outside the door to the pristine beaches, renowned local restaurants, and the vibrant Bridge Street with live music, restaurants, bars, and shopping. Our beach retreat promises an unforgettable vacation!

Gulf Front Escape + Beach Access

🦩 Exclusive Amenities Include: • Walk Out to the Beach – Steps from Your Door • Coastal & Surf Decks - Outdoor Seating • Historic Old Florida Charm • Beach Towels, Chairs & Umbrellas Provided • Community Pool with Picnic Tables & Chaise Lounges • Community Grills & Post-Beach Outdoor Showers • Free WiFi & TV • Coffee Maker & Kitchenette Smallwares Provided • Starter Packs of Essentials for Kitchen & Bath • Enhanced Cleaning Protocols • Combo Tub/Shower Bathroom • Desk/Chair in Unit

Steps to Siesta Key Beach! Sunset Balcony Views!

This beautifully appointed 2-bedroom, 1-bath condo (Sleeps 6) is centrally located directly across from the world-famous "sugar-white sands" of Siesta Key Beach. Unit 205 offers a perfect location with spectacular Gulf of Mexico sunsets from your private balcony. Enjoy a covered parking spot. The master suite has a King bed, a second bedroom with two twin beds, and a pull-out sofa in the living area. Nearby find rentals for bikes, scooters, water sports, parasailing, fishing, sunset cruise.

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

Payton's Place | Private Heated Saltwater Pool/Spa

Slow down, settle in, and soak up the island pace of life. Your family will be close to everything when you stay at this centrally located private home — just a short stroll to local restaurants, charming shops, and the free trolley stop at the end of the street by the library. The white sand beaches and turquoise Gulf waters are only a 7-minute walk away. Spend your mornings at the beach, your afternoons by the heated saltwater pool, and your evenings under the stars in your private spa.

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!

"The Lost Loon" Oceanfront Cottage by Roxy Rentals

Welcome to Lost Loon Oceanfront Cottage, a beautifully renovated 2-bedroom, 2-bath retreat on the Gulf. Enjoy private beach access, outdoor dining, and the soothing sound of waves just steps away. Inside, find a fully equipped kitchen and beach essentials like chairs, boogie boards, and games. Perfect for families, friends, or solo travelers seeking coastal comfort and charm. One pet is welcome (other pets upon request). Please note: the property is not fenced.

Black Pearl! NEW! Block and half to Beach!

Black Pearl is a brand-new luxury 4-bedroom, 4-bath home just a block and a half from the beaches of Holmes Beach. This modern coastal retreat features a rooftop deck with gorgeous views, a private pool and spa, BBQ grill, ping pong table, and corn hole. Each bedroom offers a queen bed and ensuite bath, making it perfect for families or friends seeking upscale comfort and walkable beach access on Anna Maria Island. 🏖️✨

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

Relax in this cozy 1BR beachfront duplex on Siesta Key, steps from the Gulf’s white-sand beaches. Perfect for couples or small groups, it features bright interiors, open living, and shared access to a pool, hot tub, and outdoor games. ☀ Pool access & hot tub ☀ Steps to the beach ☀ BBQ grill ☀ Life-size Connect 4 ☀Wifi and Free parking on premises ☀ Pets allowed Your perfect beach escape awaits.

Casa Bella Vita | Walk to Crescent Beach!

Exclusive Amenities Include: • Semi Private, HOA Maintained Heated Pool • Less Than 0.1 Miles to Point of Rocks Beach • 3 Bedrooms, 3 Full Baths - 1 King Bed, 1 Queen Bed, 2 Full Bed, 1 Queen Sofa Sleeper (Sleeps 10) • 4 Spacious Balconies • Elevator for Luggage, Groceries and Personal Gear • Free WiFi & 5 HDTV’s • Private 2 Car Garage with Ping Pong Table • Regular & Keurig Coffee Maker

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. 🌴

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!