House holiday rentals in Siesta Key

Siesta Key, FL - Casa Berano

Quiet, private home on lovely Siesta Key. 1.6 miles from lovely #1 Beach in the country. 1.9 miles to Siesta Key Village. FREE shuttle to village & beach 7 days a week. Private saltwater pool/enclosed lanai. Spacious 3bd/3b. Pets, dogs only, welcome, pls add to your total guest reservation. Open floor plan, large living area. Kitchen opens into living area & 2 dining areas w/ large tables. 2 car gar. brick paved driveway, in home laundry. 6 Guests Max 2 pets Max (dogs only), under 50lbs

Luxury Home Near Downtown & Siesta Key Beach

A tranquil and spacious 3BR/2BA house awaits you on a serene, traffic-free street. This luxurious abode boasts high-beamed ceilings and inviting details, creating an atmosphere that is both comfortable and refined. With its location just 7 miles from Siesta Key Beach, 6 miles from Lido Beach, and 2.5 miles from Downtown, this property offers convenience and accessibility. Enjoy your coffee on the lanai as you plan your day of exploring nearby shops and restaurants, just a short 7-min drive away.

The Mango House Beach Cottage

Our cozy boho beach cottage, The Mango House is the perfect place for a couple or small family to relax and enjoy all the best Sarasota amenities. It’s conveniently located right between both Siesta Key entrances, walking distance to restaurants, grocery stores, Trader Joe’s, gym and a block from the popular Walt’s Fish Market. This gorgeous bungalow is the front house of a duplex on a large lot with plenty of cozy private outdoor space to relax and take in all the wonderful Florida weather!

Charming Villa 14 mins away from Siesta Key Beach

This villa close to Siesta Key Beach serves as the perfect escape for those looking to enjoy Sarasota. The property comes fully equipped with amenities such as a BBQ, outdoor umbrella, lounge chairs, beach chairs, pickleball rackets, washer/dryer and carport. Featuring 2 bedrooms, this charming home exudes a warm vibe. You can reach Siesta Key Beach, St. Armands Circle, and Downtown Sarasota in under 15 minutes, making it easy to explore all that Sarasota has to offer during your stay.

Your private retreat near Siesta Key Beach.

Completely Remodeled Private Retreat. COME RELAX, UNWIND, AND MAKE LASTING MEMORIES! From the moment you arrive, you’ll feel the calm, welcoming atmosphere that makes this property stand out. This spacious 3brm 2-bath features an amazing heated pool, a private backyard, and stylish finishes throughout. Whether you’re lounging by the heated pool, enjoying meals in the bright open-concept living space, or exploring the nearby beaches this home is perfect for an unforgettable vacation

Beach Retreat•Renovated Pool Patio•Near Siesta Key

Stay at one of Sarasota’s top-rated Airbnbs, perfectly centered between the ever famous Siesta Key and several other stunning beaches. Lounge by the newly renovated heated pool with upscale chaise lounge chairs, lush garden views, and a stylish patio with ample seating. Inside, enjoy a modern, beach vacation themed design with an open layout, fully stocked kitchen, fast WiFi, and Smart TVs in every bedroom. Your on-site Superhost is nearby but works full time and gives total privacy.

Comfortable + Functional Private Studio Apartment

This comfortable, clean, and private studio apartment is the perfect spot to relax- whether you're here on business or you've spent the whole day on the beach! Recently remodeled with a dining table to take your meals, hot water, a comfortable bed, and well equipped kitchenette, you will be lacking nothing here. This apartment is a guest suite attached to the main living area of the home and is completely private, however there is a resident who lives in the main part of the home.

Roselawn St | Private Pool, Fire Pit + Patio!

BNB Breeze Presents: Roselawn Street! Located in the heart of Sarasota, just 10 minutes away from Siesta Key Beach, the location of this home is everything! This stunning oasis with a private pool and basketball court includes: • Private Heated Pool - heated at NO extra cost from Nov 21 - April 1st • Miniature Basketball Court • Covered Outdoor Dining Area + Grill • Lightning Fast Wi-Fi (Perfect for Remote Work!) • Incredible Fire Pit w/ String Lights! • 2 Living Rooms

Charming Apt. in old Florida home

Cozy, charming suite in a historic 1920's home. Lots of character and charm. Amazing location. One block from the bay with beautiful sunsets. And just a few miles to the beach and downtown. Clean, comfy and a welcoming host. Great for 1 or up to 3 guests. ****Please read the full detailed description for more information before booking. This is very old home, not fully restored, old Florida house. Owner occupied Non- Smoking guests 🙏 Hope to see you soon

Relaxing 3BR Retreat+ Hot Tub + Pool +Beaches +IMG

🌴Welcome to Beachway Haven! This 5-Star ⭐️ hideaway is just mins from Anna Maria Island's Pristine Beaches & the Gulf of Mexico. Dive into relaxation with your own Heated Saltwater Pool & Spa Hot Tub, nestled in a tropical oasis. Only a skip away from Golf Courses, Nature Parks, IMG Academy, & Palma Sola Causeway's Beach Access – your gateway to Horseback Riding, Kayaking, & endless sandy adventures. Shopping & dining are only a few mins away too!

Palm Retreat Gold: Luxury Edition of #1 Rental

High end, luxury 3/2 pool home! 7 4k TVs w/ Netflix and cable (75" in living room), SONOS throughout house/pool, wifi, PS5, private heated salt water pool/Spa, putt putt, foosball, beach gear, Pack & Play, Game room (board games, billiards, shuffle board, arcade), massive kitchen/bar, washer & dryer, garage parking-- all in a quiet and safe neighborhood. Just 5 miles to the best beaches and restaurants. Entire home with no shared amenities!

1 Bed 1 bath 7 mins to the beach

This charming 1 bedroom 1 bath space has a calming coastal vibe with dedicated driveway parking, front porch, and fenced backyard. This unit is newly renovated and furnished, and is part of a duplex with a large shared backyard. It is within walking/biking distance or a short drive to grocery stores and restaurants, and 7 mins to Siesta Key - FL's #1 beach! Longboat Key, St. Armands, Turtle Beach, and Downtown are all a short drive away!