Siesta Chillin Resort Condo Steps from #1 Rated Beach

Open Living Area - Enter your air conditioned condo with an open concept design
Open Living Area - Enter your air conditioned condo with an open concept design
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Open Living Area - Enter your air conditioned condo with an open concept design

About the Property

  • Sleeps: 6
  • Bedrooms: 2
  • Bathrooms: 2
  • Property Type: Condo
  • Minimum Stay: 7 nights
  • Living Area: 1280 sq. ft.

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 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 from 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 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! 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 VTrips. Contact us for the VTrips link to view current availability, exact rates for your specific dates, and to book 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.

Amenities

  • Beds
  • 1 King Bed
  • 2 Queen Beds
  • Features
    • Air Conditioning
    • Balcony
    • Beach Chairs
    • Communal Pool
    • Dock / Boat Slip
    • Elevator
    • Fitness Room
    • Free WiFi
    • Full Kitchen
    • Heated Pool
    • Heating
    • Internet
    • Kid Friendly
    • Linens Provided
    • Managed by Property Manager
    • No Pets Allowed
    • Non-Smoking
    • Parking
    • Towels Provided
    • Water View
    • Wireless Internet
  • Appliances
    • Blender
    • Cable / Satellite TV
    • Ceiling Fans
    • Coffee Maker
    • Dishes & Utensils
    • Dishwasher
    • DVD Player
    • Freezer
    • Hair Dryer
    • Iron & Board
    • Microwave
    • Outdoor Grill
    • Oven
    • Refrigerator
    • Stove
    • Telephone
    • Television
    • Toaster
  • Nearby Activities
    • Basketball Court
      (onsite)
    • Boating
      (onsite)
    • Gym/Fitness Center
      (onsite)
    • Tennis
      (onsite)
    • Beach
      (< 1 mile)
    • Bicycling
      (< 1 mile)
    • Deep Sea Fishing
      (< 1 mile)
    • Fishing
      (< 1 mile)
    • Grocery Store
      (< 1 mile)
    • Jet Skiing
      (< 1 mile)
    • Kayaking
      (< 1 mile)
    • Live Entertainment
      (< 1 mile)
    • Ocean
      (< 1 mile)
    • Parasailing
      (< 1 mile)
    • Park
      (< 1 mile)
    • Snorkeling
      (< 1 mile)
    • Windsurfing
      (< 1 mile)
    • Shopping Area
      (3 miles)
    • Golf
      (5 miles)
    • Movie Theater
      (5 miles)
    • Zoo
      (5 miles)

Other Vacation Rental Amenities

We supply beach towels, beach chairs, umbrella, beach cart, beach toys.

Bicycles and golf carts can be rented across the street.

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Rates

Rental basis: Per property
Rental rates quoted in 
Rate PeriodNightlyWeekend NightWeeklyMonthlyMin Stay
Feb 01 2021 - Apr 30 2021
$195 7 nights
May 01 2021 - Nov 12 2021
$135 $3,445 7 nights
Nov 13 2021 - Jan 14 2022
$165 $4,210 7 nights
Jan 15 2022 - Apr 29 2022
$205 $5,230 7 nights

Fees:

Damage Protection: $99

Tax Rate: 12%

Notes:

To provide a top-notch guest experience, Siesta Chillin is managed by VTrips. Contact us for the VTrips link to view current availability, exact rates for your specific dates, and to book online.

Standard rates are shown which do not include owner special discount for April rentals.

7 night minimum rental. Saturday arrival or Saturday departure required for rentals less than 20 nights.

Guests are not charged a cleaning fee

VTrips charges a 5% booking fee

Availability


Please inquire about availability.

Map

Nearest Airport: Sarasota Bradenton International Airport (SRQ) - 10 miles
Nearest Bar: Daiquiri Deck - 100 yards
Nearest Beach: Siesta Key Crescent Beach - 200 yards
Nearest Restaurant: 6 great restaurants of varying cuisines - 200 yards

Owner Info

Laura Ainsworth

Laura Ainsworth

About the owner: In 2003, we visited family who had recently moved to Sarasota County and we spent a lot of time exploring the coastal areas. We literally stumbled upon Siesta Key and immediately fell in love with the place. Ten years later, we fulfilled our dream of owning a nice getaway on Siesta Key. Someday, the Sarasota area will be our permanent home. Until then, we hope you come to Siesta Chillin and fall in love with Siesta Key just like we did!

Why this property? 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, be 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 with balcony access. The condo is very spacious with a noticeable absence of clutter to create a relaxing environment for our guests. 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.

Guestbook comments from the owner:

I would definitely do it again


Dec 2020

This is our second stay in this condo. Had such a good experience, needed to share it! First, the condo is spacious & the updates make it even more inviting and clean. Really liked that the unit had plenty of beach gear (chairs, floats, umbrellas, etc...) and that the kitchen was well-provisioned. What we really love is the location – across the street from a stunning beach, fishing on the Intercoastal Waterway in the shaded bbq/picnic area on property, numerous restaurants & a grocery store in a 3-block radius. Only wish was to have more time to spend here!


Oct 2020

Great condo and location in beautiful Siesta Key.


Dec 2019

Great time, thank you! We stayed in this condo at the Anchorage for a fun girls weekend and it was terrific! The condo was clean and spacious with lots of room for all of us and our suitcases! The bedrooms were quite large which is unusual for a beach condo. The condo was in a great location as we could walk to a lot of areas including the beach across the street. We will definitely be back!


Sep 2019

My family very happy to be there


Jul 2019

We spent one week (from Saturday to Saturday) in a beautiful apartment on the third floor. Although we have been going to Siesta Key since the late 1970s, this was our first time at Anchorage. And we loved it! Two extra details: our apartment did not have covered parking space and the office found us one. After getting home we realized we had left one book and two addressed and phone books in the apartment. They waited until the new tenants left and went to check. She found them!


Jul 2018

Anonymous

Photos

  • Open Living Area - Enter your air conditioned condo with an open concept design
    Open Living Area - Enter your air conditioned condo with an open concept design
  • Sit Back and Relax - The main living area has comfortable seating and a large TV
    Sit Back and Relax - The main living area has comfortable seating and a large TV
  • Lots of Light - With a wall of sliding glass doors, you will get your vitamin D!
    Lots of Light - With a wall of sliding glass doors, you will get your vitamin D!
  • Bond Over a Family Meal - Serve four around the dining table, plus 2 at the bar
    Bond Over a Family Meal - Serve four around the dining table, plus 2 at the bar
  • The breakfast bar is a great place to enjoy a beverage and hang with the chef
    The breakfast bar is a great place to enjoy a beverage and hang with the chef
  • Fully Stocked Kitchen - Impress your friends by preparing your favorite recipes
    Fully Stocked Kitchen - Impress your friends by preparing your favorite recipes
  • Spacious Primary Bedroom - You'll sleep wonderfully in the king-sized bed
    Spacious Primary Bedroom - You'll sleep wonderfully in the king-sized bed
  • Private Outdoor Access - Step out onto the balcony and enjoy the sunshine
    Private Outdoor Access - Step out onto the balcony and enjoy the sunshine
  • En Suite Master Bathroom - Two sinks in a separate area means no waiting
    En Suite Master Bathroom - Two sinks in a separate area means no waiting
  • Room to Sleep Six - The second bedroom includes two queen beds
    Room to Sleep Six - The second bedroom includes two queen beds
  • Late-Night TV - Both bedrooms have a wall-mounted TV with cable service
    Late-Night TV - Both bedrooms have a wall-mounted TV with cable service
  • Linens Included - Bathrooms stocked with plenty of towels
    Linens Included - Bathrooms stocked with plenty of towels
  • Step Outside - The balcony beckons you through sliding glass doors in every room
    Step Outside - The balcony beckons you through sliding glass doors in every room
  • Welcome to Siesta Chillin - You will be relaxed in no time on this sunny balcony
    Welcome to Siesta Chillin - You will be relaxed in no time on this sunny balcony
  • Reserve Your Visit to Paradise - You are in for a treat at Siesta Chillin
    Reserve Your Visit to Paradise - You are in for a treat at Siesta Chillin
  • Wonderful Gulf Living - The Anchorage resort has all the comforts you desire
    Wonderful Gulf Living - The Anchorage resort has all the comforts you desire
  • Splash Around - A large heated pool with sundeck and a clubhouse for guests
    Splash Around - A large heated pool with sundeck and a clubhouse for guests
  • Playtime - Outdoor fun with tennis, shuffle board, and basketball courts
    Playtime - Outdoor fun with tennis, shuffle board, and basketball courts
  • Steam Away - Follow up your exercise routine with a visit to the sauna
    Steam Away - Follow up your exercise routine with a visit to the sauna
  • Beach Life - One of the top rated beaches in the world is only a 5 minute stroll
    Beach Life - One of the top rated beaches in the world is only a 5 minute stroll
  • Unforgettable Sunsets - Watching the amazing Siesta Key sunsets never gets old
    Unforgettable Sunsets - Watching the amazing Siesta Key sunsets never gets old

Reviews

Date last modified: February 14th, 2021

Contact Owner

Email Owner