Experience the Ultimate Siesta Key Beach House Lifestyle
Brand New Luxury Rentals. Modern Amenities. Zero Booking Fees.
Browse our portfolio of properties and book your unforgettable escape today!
The Sand Dollar on Siesta
Escape to unparalleled luxury at this brand-new, exquisitely built vacation rental, completed in June 2025, and ideally situated just steps from the vibrant Siesta Key Village. This magnificent retreat boasts 6 spacious bedrooms, each with its own en-suite bathroom, plus an additional half-bath for ultimate convenience, comfortably accommodating large families or groups.
Experience effortless living with a private elevator servicing all levels. The heart of the home is a state-of-the-art gourmet kitchen, fully equipped with high-quality appliances and ample counter space, perfect for culinary enthusiasts.
Canal Upper – Gorgeous 3 bed 3 bath near SK Village
Escape to Canal Upper, a beautifully designed getaway just minutes from Siesta Key Beach, ranked the #1 beach in the U.S.! This spacious 3-bedroom, 3-bathroom home offers a modern kitchen with stainless steel appliances and a dining area that comfortably seats six.
Everything you need for the ultimate beach day is provided: beach carts, chairs, and towels, making the 5-6 block stroll to Beach Access #5 effortless. After a day in the sun, unwind in your private outdoor oasis, complete with a tranquil pool, relaxing hot tub, and BBQ area, perfect for family gatherings or a peaceful evening under the stars.
Canal Lower – Gorgeous 3 bed 3 bath near SK Village
Welcome to Canal Lower, a beautifully designed retreat just minutes from Siesta Key Beach! Inside, the open-concept living space and modern décor create a bright, inviting atmosphere. The fully equipped kitchen is perfect for preparing meals to enjoy on the patio under the stars.
Each of the three bedrooms features a private en-suite bathroom, ensuring comfort and privacy for everyone. Plus, enjoy the convenience of an in-unit washer and dryer, as well as beach chairs and towels for effortless beach days.
Pineapple on Siesta
Open-concept living space meets modern décor, creating a bright and inviting atmosphere. The fully equipped kitchen is perfect for preparing meals to enjoy on the patio under the stars.
Each of the three bedrooms features a private en-suite bathroom, ensuring comfort and privacy for everyone. Plus, enjoy the convenience of an in-unit washer and dryer, as well as beach chairs and towels for effortless beach days.
The Pelican on Siesta
Step into your perfect Siesta Key escape! This charming upper-level is just two blocks from the crystal-white sands of Siesta Key Public Beach. Enjoy the best of Florida living with your own private, caged swimming pool.
The spacious interior is ideal for families and friends. Features include a full kitchen, a comfortable living area, and a private balcony. Walk to the beach, grab dinner, or explore the village. Your unforgettable island vacation starts here!
Beachy Sarasota Duplex
Enjoy a stylish experience at this centrally-located place just minutes from Siesta Key Beach. Newly renovated duplex, 5 blocks from Stickney Point Bridge leading to Siesta Key.
Beach theme throughout for a relaxing vibe with updated amenities of a home. Beautiful backyard with Swim Spa, Gas Fire Pit, Gas Grill, and plenty of seating. Located near restaurants, museums, shopping, and Siesta Key Beach. Beach carts, chairs, and towels are provided to head over to the island for a fabulous beach day!
Sarasota Duplex near Siesta Key
Perfect for couples or families looking for a comfortable and convenient vacation rental.
This newly renovated duplex exudes beach vibes and is the perfect spot for a relaxing vacation. Located just a few blocks from Stickney Point Bridge, which leads directly to the beautiful Siesta Key Beach, you’ll have easy access to all the fun and sun that Florida has to offer.
Cozy Home on Lake Winnebago
Enjoy a tranquil retreat perfect for the whole family at this serene lakeside property. Conveniently located near restaurants and shopping, it features a private sandy beach for your exclusive use.
Public boat launches are just a mile away in either direction, offering easy access to the water. Take advantage of the available paddleboards and paddleboats for sunny day adventures, or explore the lakefront on your ATV for an exciting ice fishing experience.
Step Into the Sand: Beachfront & Village Proximity Rentals
#1 Beach in the USA
Simply the BEST! Siesta Key Beach was voted the #1 beach in the US by Trip Advisor in 2024
4th Best Beach in the World
Siesta Key Beach voted the 4th best beach in the WORLD to visit by Trip Advisor’s Traveler’s Choice Awards in 2024
White Beaches, Pristine Waters
Siesta Key Beach is unparalleled, characterized by quartz white sands and swimmable, warm Atlantic Ocean waters
Highly Rated Homes
Rated an average of 4.7 to 5 stars consistently by guests, our vacation homes are the perfect choice for your getaway
Conveniently Located
Conveniently located near Siesta Key’s beaches, dining, shopping and local activities.
Amenities & Rentals
All the comforts of home with the perks of the resort life to keep you comfortable and active.
Welcome to Vacation On Siesta!
We’re Marcus and Nicki, and we’re thrilled that you’re considering Siesta Key for your next vacation. We’re passionate about this beautiful island and love sharing its magic with visitors like you.
We’ve explored every corner of this paradise, from the world-renowned, powdery white sands of Siesta Beach to the charming village shops and restaurants. Now, we’re excited to help you create unforgettable memories here.
We take pride in providing high-quality, comfortable accommodations because we believe your vacation should be relaxing and stress-free, starting with the perfect place to call home during your stay.
We believe that Siesta Key offers something for everyone, whether you’re looking for a relaxing beach getaway, an adventurous exploration of nature, or a fun-filled family vacation. We’re excited to help you find the perfect rental and make the most of your time on this stunning island.
Skip the Fees and Book Your Siesta Key Escape Direct
Siesta Key isn’t just a destination; it’s an escape into pure coastal bliss. As the #1 beach in the U.S., this barrier island off Sarasota’s coast is known for its powdery white sand, crystal-clear waters, and laid-back charm. From the vibrant energy of Siesta Beach and the hidden gems of Crescent Beach’s Point of Rocks to the serene shores of Turtle Beach, every corner of Siesta Key offers something unique.
At Vacation on Siesta, we’re your key to the ultimate island experience. Whether you’re searching for the perfect beachfront stay, local dining hotspots, or unforgettable activities, we make planning your dream getaway effortless. Let us show you Siesta Key the way it was meant to be enjoyed.
