Siesta Chillin Resort Condo Steps from #1 Rated Beach

SIESTA SUMMER SAVINGS! UP TO 20% OFF YOUR SUMMER STAY BETWEEN 5/31/25 AND 9/1/25 WHEN BOOKING DIRECTLY ONLINE
Online booking: Click link in Host information section of this listing and use promo code Anchor6415 at checkout

We invite you to stay in our spacious 2 bed 2 bath condo, 'Siesta Chillin', across from the beautiful crystal sands of Crescent Beach on Siesta Key. Siesta Chillin has been recently updated and has all the conveniences of home in an amazing vacation spot at The Anchorage Yacht and Tennis Club.

When you walk through the front door, a large and welcoming space greets you with our freshly renovated open-concept kitchen, quality furnishings, new floors, and luxury linens. Siesta Chillin is a very large unit at 1280 square feet. Everyone loves the spacious balcony that covers the entire width of the condo so it is accessible from the living room and both bedrooms. Southern exposure makes the condo bright and cheerful with picturesque views through the sliding glass doors in every room. The condo complex backs up to the Inter-Coastal Waterway with a serene park-like setting. Amenities include a heated Olympic-sized pool, lighted tennis and shuffleboard courts, BBQ grills, exercise room, saunas, and free boat docking.

Everything you need is within walking distance of The Anchorage resort. The main attraction, the #1 rated Siesta Key Crescent Beach, is less than 10 minutes walk from the front door of Siesta Chillin. The beach, market, charter boats, fishing equipment, jet ski rentals, kayak/paddleboard rentals, para-sailing, and bike rentals are just across the street. Convenience stores and several great dining establishments are only a short stroll across the street to the hidden treasure of Siesta South Village. There is even some of Sarasota's best Karaoke! The Anchorage has private gated access to Siesta Key Crescent Beach across the street. You can also hitch a free ride (tips appreciated) to Siesta Key Village, where a wide range of shopping and dining fun awaits. Or, hop in your car and explore the local attractions of Sarasota and St. Armand's Circle.

Siesta Key is truly a little slice of heaven for everyone in the family, from grandparents to young children. Siesta Chillin is the perfect location for an amazing Siesta Key experience - whether you are staying for months to escape the northern winters or taking a short getaway to relax and rejuvenate. Come and chill with us in Siesta Key!

To provide a top-notch guest experience, Siesta Chillin is managed by the in-house Anchorage Community Rental Program. Click the link in the Host information section of this page for the live listing at The Anchorage where you can view availability, final quotes, and book directly online.

Unique Benefits

Where you stay in Siesta Key really matters - the location and value of Siesta Chillin is second to none! We looked at every condo complex on the Key and chose our unit at The Anchorage. Other condo units of similar size, luxury, and amenities will cost more, have less space, are a 1/4 mile or more from beach access, or require driving to simple conveniences like groceries and restaurants. For added safety, the complex has secure building access with interior corridors.

The sunrise from Siesta Chillin's balcony is absolutely breathtaking! You can rejuvenate your mind and soul as you relax and enjoy your hot beverage while watching the sun come up. The large sliding glass door to the balcony and southern exposure keeps the condo bright and when open creates an indoor-outdoor living room. Another unique feature is that each bedroom has a large sliding glass door which is like a wall of windows with balcony access. The condo is very spacious with a noticeable absence of clutter to create a relaxing environment for our guests. Your car can also take a vacation - Siesta South Village is only a short walk to everything you need including groceries, cocktails, supplies, and some of the best dining venues on the key.

Why Kids Love It

Young kids love being in the water. The Anchorage pool is fabulous and one of the largest on Siesta Key. Crescent Beach has wonderful crystal blue waters that is shallow near the shore and one of the safest in the country for small children. The powdery white sand is perfect for building sandcastles. Kids also love ice cream and there is plenty of it in Siesta Key!

Teenagers love Siesta Key too. They can safely roam in groups independently without getting into trouble. No driving is necessary - bicycles and trolleys are easily available.

Area Information

Outdoor activities abound in this area of Florida. Walk the crystal sands of Crescent and Siesta beaches. Boat, bike, and kayak rentals are right across the street with free boat docking available at the condo complex.

We have visited many beaches around the world, and Crescent Beach is truly deserving of its #1 status. The fine white powdery sand feels good on the feet, even on the hottest days. A short stroll from the condo will take you to Point Of Rocks for excellent shelling and snorkeling opportunities. Or get out in a boat or kayak to explore the mangroves and visit with the dolphins and manatee that frequent the inter-coastal waters.

Everything you need for the business of life is available within a two minute walk. The 'South Village' offers restaurants, night life, banking, market, post office, shopping and a pharmacy.

Want quick and easy access to the 'North Village's' many shops, restaurants and bars? A free shuttle bus will pick you up right by the complex and take you there and back (tips welcomed).

Downtown Sarasota is just a short drive away and offers attractions like the Ringling Museum, Van Wezel Performing Arts Hall and the Sarasota Classic Car Museum (to name but a few). For baseball fans, the Orioles spring training at Ed Smith Stadium is a fantastic family outing.

If you haven't visited Sarasota and Siesta Key before, you will soon learn it is truly one of the most beautiful locations in the country while also offering culture and family friendly attractions.

Attractions Within Walking Distance

Everything you need is within walking distance from The Anchorage. The market, charter boats, fishing equipment, jet ski rentals, kayak/paddleboard rentals, para-sailing, and bike rentals are just across the street. Convenience stores and several great dining establishments are only a short stroll to the hidden treasure of Siesta South Village. There is even some of Sarasota's best Karaoke! You can also hitch a free ride (tips appreciated) to Siesta Key Village where a wide range of shopping and dining fun awaits.

THE big attraction is Siesta Key Crescent beach which is rated the top beach in the USA. The Anchorage has a private beach access across the street and you'll be dipping your toes in the aqua blue waters of the Gulf less than 10 minutes walk from the front door of Siesta Chillin.

Favorite Places To Eat

Within 5 minutes walk from the front door of Siesta Chillin, you will arrive at the South Village. For casual dining, check out Captain Curt's, Sniki Tiki, Spearfish Grill, Big Water Fish Market, and the Daiquiri Deck. Check out Clayton's for a little more upscale dining and fantastic service. For fine dining on date night, check out Ophelia's which is one of the best restaurants in Florida.

For even greater variety, check out the North Village which is a free 10-minute trolley ride away. Some of our favorite places are The Lobster Pot, The Summer House, Another Broken Egg, The Cottage, and a local favorite - SKOB.

Ice cream is a big thing in Siesta Key and there are several fantastic creameries. The Orange Octopus in the South Village and Big Olaf Creamery in the North Village are local favorites.

Inside Scoop

Join the Siesta Key Drum Circle on Sunday evening an hour before sunset. It is a unique and spiritual experience.

If you have young children and are looking for a different type of activity, check out Jungle Gardens which is a 10 minute drive away.

For baseball fans, the Grapefruit League plays 15 minutes away at Ed Smith Stadium which is the spring training home of the Baltimore Orioles.

Phenomenal shopping and outdoor dining can be found at St. Armand's Circle which is a 20 minute drive away.

For a different type of water experience, rent a boat from CB's across the street. As you cruise the intercoastal, you will come across dolphins and the occasional manatee. Cruise up to Sarasota Bay, beach up on the sandbar, collect some shells.

Fishing in this part of Florida is terrific! Get your bait from CB's across the street and fish the intercoastal in back of the Anchorage. Check with the helpful folks at CB's for hot fishing spots you can get to by boat or do a fishing/sightseeing charter.