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
1/23
1/23
Open Living Area - Enter your air conditioned condo with an open concept design

Siesta Chillin Resort Condo Steps from #1 Rated Beach

About this rental

Condo (Sleeps 6)
1280 sq. ft.  ·   2 bedrooms   ·  2 bathrooms
Siesta Key Condo
  • Sleeps 6
  • 2 bedrooms
  • 2 bathrooms
  • 1280 sq. ft.
3 reviews
  • Sleeps: 6
  • Bedrooms: 2
  • Bathrooms: 2
  • Property Type: Condo
  • Minimum Stay: 7 nights
  • Living Area: 1280 sq. ft.

DISCOUNT SPECIAL - 15% OFF THE PUBLISHED RATE FROM JULY 1 - July 14

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 now managed by the in-house Anchorage Community Rental Program. Contact us if you have questions and for the direct link to book with The Anchorage online or via phone.

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.

View more

Amenities

Beds
  • 1 King Bed
  • 2 Queen Beds
Features
  • Air conditioning
  • Balcony
  • Beach chairs
  • Bed linens provided
  • Communal pool
  • Dock or boat slip
  • Elevator
  • Fitness room
  • Heated pool
  • Heating
  • Internet
  • Kid friendly
  • Kitchen
  • Managed by property manager
  • No pets allowed
  • Non-smoking
  • Parking available
  • Towels provided
  • Water view
  • WiFi
  • Wireless internet
Appliances
  • Blender
  • Cable / satellite TV
  • Ceiling fans
  • Coffee maker
  • DVD player
  • Dishes & utensils
  • Dishwasher
  • Freezer
  • Hair dryer
  • Iron and board
  • Microwave
  • Outdoor grill
  • Oven
  • Refrigerator
  • Stove
  • Telephone
  • Television
  • Toaster
Nearby Activities
  • Basketball Court
    (onsite)
  • Beach
    (< 1 mile)
  • Bicycling
    (< 1 mile)
  • Boating
    (onsite)
  • Deep Sea Fishing
    (< 1 mile)
  • Fishing
    (< 1 mile)
  • Golf
    (5 miles)
  • Grocery Store
    (< 1 mile)
  • Gym/Fitness Center
    (onsite)
  • Jet Skiing
    (< 1 mile)
  • Kayaking
    (< 1 mile)
  • Live Entertainment
    (< 1 mile)
  • Movie Theater
    (5 miles)
  • Ocean
    (< 1 mile)
  • Parasailing
    (< 1 mile)
  • Park
    (< 1 mile)
  • Shopping Area
    (3 miles)
  • Snorkeling
    (< 1 mile)
  • Tennis
    (onsite)
  • Windsurfing
    (< 1 mile)
  • 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
Sep 09 - Nov 17 2024
$155 7 nights
Nov 18 - Nov 24 2024
$210 7 nights
Nov 25 - Dec 15 2024
$170 7 nights
Dec 16 - Dec 29 2024
$295 7 nights
Dec 30 2024 - Jan 12 2025
$210 7 nights

View all periods

Fees:

Refundable Damage Deposi: $400
Cleaning Fee: $155
Booking Fee: $125

Tax Rate: 13%

Notes:

To provide a top-notch guest experience, Siesta Chillin is managed by the in-house Anchorage Community Rental Program. Contact us if you have questions and for the direct link to book with The Anchorage online or via phone.

7 night minimum rental. In peak season, Saturday arrival and Saturday departure required.

$400 deposit required to hold a reservation
50% due 60 days prior to arrival
Full amount due 30 days prior to arrival

Availability

Last updated on January 02, 2024

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20Available     20Unavailable     20Today

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

Hosted by Laura Ainsworth

Laura Ainsworth

Member since 2021

Year Purchased: 2013

About the owner: In 2003, we visited family who recently moved to Sarasota County and 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 host:

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
  • Perfect Location - The Anchorage resort is a short walk from village and beach
    Perfect Location - The Anchorage resort is a short walk from village and beach
  • 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
  • Resort Living - The Anchorage is known for its wonderful amenities
    Resort Living - The Anchorage is known for its wonderful amenities
  • 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
  • Relaxing Back Yard - Watch boats go by, play games, or fish on the Intercoastal
    Relaxing Back Yard - Watch boats go by, play games, or fish on the Intercoastal
  • BBQ Time - Park like setting with grills and seating
    BBQ Time - Park like setting with grills and seating
  • Unforgettable Sunsets - Watching the amazing Siesta Key sunsets never gets old
    Unforgettable Sunsets - Watching the amazing Siesta Key sunsets never gets old

Reviews

from 3 reviews
Write a review
review

Siesta Central - The Anchorage!!

We stayed at the Anchorage in unit 305. It faces the city and the inner coastal lagoon. We were treated to a dolphin show one evening when they entered the lagoon searching for food!! This location is perfect for walking access to restaurants, groceries, and the beach. Our condo was large and comfortable. The only thing we would wish for are new bed sheets. They should be a focus for guests who are doing extended stays. We have already booked our two weeks for 2024 at the same location!

Stayed: Submitted: January 21, 2023

Owner response

Thank you for the helpful review. We are so glad you enjoyed your stay at Siesta Chillin. What an exciting treat to see the dolphins!

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review

Beautiful condo

We had an amazing stay at siesta chillin. The check in process was very easy and if we needed anything there was somebody to help very quickly. The staff at the anchorage were so kind and helpful. The layout of the condo was perfect with glass doors across the entire living area and both bedrooms. The balcony was huge! The kitchen was fully stocked and anything we needed for the beach was supplied as well. Including a wagon to pull everything if you have little kids. The beach was right across the street and was so beautiful. The pool area was wonderful as well. Behind the condo is a quaint little area on the bay where I saw many dolphins and manitees swim by. The only complaint I would have is that it is very close to the Stickney point bridge and you can hear the traffic noise from the condo and on the balcony. But that wouldn’t stop me from coming back to siesta chillin. We are counting down the days until we can come back

Stayed: Submitted: December 14, 2022

Owner response

Dear Jennifer, we are so happy you enjoyed your stay at Siesta Chillin! Thanks for taking the time to provide this helpful review. We look forward to hosting you at Siesta Chillin in the future.

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review

Beach condo

Condo was in a great location with easy beach and bay access. Plenty of room for a family of 5. Grocery stores and dining within driving distance. Older unit, but in adequate repair and clean.

Stayed: Submitted: July 03, 2022

Owner response

Dear Eric, thank you for choosing to stay at Siesta Chillin and providing a helpful review. We are glad you found the location convenient, spacious, and clean. We hope to host you again at Siesta Chillin!

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Laura Ainsworth

Hosted by Laura Ainsworth

Contact Host