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Book Online or call HomeAway Booking Assistance +44 (0) 800 917 5992

Beach paradise at the right price ** $250 DISCOUNT IN APRIL 2017 **

Bedrooms 2
Space 1,280 sq. ft.
Property type condo
Minimum Stay 7 nights
Popular Features
  • Internet
  • Washing Machine
  • Parking
  • non smoking only
  • Air Conditioning
  • Barbecue
  • children welcome


About the property

Spacious and bright 2 bedroom 2 bathroom condo steps from the #1 rated beach

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 all the conveniences of home in an amazing vacation spot at The Anchorage Yacht and Tennis Club. Siesta Chillin costs less than comparable vacation rentals because we do not charge additional cleaning or booking fees.

When you walk through the front door, a large and welcoming space greets you with our freshly renovated open-concept kitchen, updated baths, quality furnishings 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.

The location of Siesta Chillin is terrific! Our guests love the convenience of private access to the #1 rated beach in the United States: Siesta Key Crescent Beach. Within 5 minutes walk, you will be touching the most exquisite quartz crystal sand and calm aqua waters that stretch for miles. For the convenience of our guests, we provide all the items needed for the beach including a beach cart, umbrella, chairs, and beach toys. When you stay at Siesta Chillin, all you need is a swim suit and flip-flops and you are ready for a Siesta Key beach vacation.

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. 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!

More Details

Laura Ainsworth
Member since: 2014
Speaks English
Response time:
Within a few hours
Response rate:
Calendar last updated:
25 March, 2017

About Laura Ainsworth

We are Stuart and Laura from the Annapolis, Maryland area. 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!

Laura Ainsworth purchased this condo in 2013

Why Laura Ainsworth chose Florida South Central Gulf Coast

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 Anchorage does an excellent job managing our condo and the friendly staff makes sure guests have a pleasant and trouble free stay.

What makes this condo unique

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. 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.

For the convenience of our guests, there are NO CLEANING OR BOOKING FEES. Check out the reviews and compare prices and you will find that Siesta Chillin is one of the best values on the key.


Accommodation and facilities for this holiday condo in the Siesta Key in the Manatee County

Property Type:
  • condo
  • floor 3
Building Type:
  • building
  • Self-catering
Floor Area:
  • 1280 sq. ft.
House Rules:
  • Max. occupancy 6
  • non smoking only
  • pets not allowed ...
  • Minimum Age Limit for Renters ...
  • children welcome
Location Type:
  • city centre ...
  • near the sea ...
  • village ...
  • Water View ...
  • Waterfront
  • Away From It All
  • Family
  • Romantic
  • Sports & Activities
  • Tourist Attractions
  • Air Conditioning
  • Lift
  • Fitness Room / Equipment ...
  • Heating
  • Internet ...
  • Iron & Board
  • Linens Provided
  • Living Room
  • Parking ...
  • Telephone
  • Towels Provided ...
  • Washing Machine ...
  • Coffee Maker
  • Dishes & Utensils
  • Dishwasher
  • Kitchen ...
  • Microwave
  • Oven
  • Pantry Items
  • Refrigerator ...
  • Hob
  • Toaster ...
  • Dining Area
  • seating for 6 people
  • 2 Bathrooms
  • Master - Toilet , Shower Enclosure
    Second - Toilet , Bath (no shower) , Shower Enclosure
  • 2 Bedrooms, Sleeps 6
  • Master - 1 Extra Lg. Double Bed
    Second - 2 Large Double Bed , Recently upgraded with two beautiful new queen beds!
  • Both bedrooms have a walk-in closet, vanity, chair, flat screen TV, and sliding glass door with balcony access
  • Books ...
  • DVD Player ...
  • Satellite / Cable ...
  • Stereo ...
  • Television ...
  • Video Library ...
  • Balcony ...
  • Boat ...
  • Garden
  • Barbecue ...
  • Tennis ...
  • Long-term Renters Welcome
  • wheelchair accessible
Pool / Spa:
  • Communal Pool ...
  • Sauna ...
  • botanical garden
  • churches
  • cinemas
  • marina
  • museums
  • restaurants
  • zoo
Leisure Activities:
  • beachcombing
  • Boating
  • Shelling
  • Shopping
  • Shuffleboard
  • walking
Local Services & Businesses:
  • ATM/bank
  • groceries
  • hospital
Sports & Adventure Activities:
  • Basketball Court
  • cycling
  • fishing
  • golf
  • jet skiing
  • Kayaking
  • Parasailing
  • sailing
  • Snorkeling/Diving
  • swimming
  • tennis
Private beach access across the street


Wonderful! 4.8/5 -
(12 traveller reviews)

Beach paradise at the right price ** $250 DISCOUNT IN APRIL 2017 **
average rating of 4.75 based on 12 reviews


  • 5 of 5

Clean, friendly, convenient to beach and everything.

  • Review Submitted: Mar 13, 2017
  • Date of Stay: Mar 2017
  • Source: VRBO, from HomeAway
Did you find this review helpful?
0 0

Great trip! Perfect weather!

  • 4 of 5

We had a great time! The owners were super easy to work with. The carpets were very dirty and stained when we arrived. I texted the owner and they had them cleaned the very next day. Had everything we needed...except beach towels. Very nice location. Thank you. We hope to make it an annual trip!

  • Review Submitted: Mar 4, 2017
  • Date of Stay: Feb 2017
  • Source: VRBO, from HomeAway
Did you find this review helpful?
0 0
Goode, VA

Walking distance to beach. Bed was comfortable.

  • 4 of 5

The carpet was stained in spots but the overall appearance of the unit was clean. The location was good and the nearby beach was beautiful and less crowded than the Siesta Key Public Beach. There was some road noise but not enough to affect our sleep. It was necessary to cross a busy road to get to the beach but there were crosswalks with lights.

  • Review Submitted: Jan 20, 2017
  • Date of Stay: Dec 2016
  • Source: HomeAway
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0 1

We really enjoyed our stay.

  • 4 of 5

Property was very well maintained and inviting. Condo was very nice and well maintained.

Street sweeper at 4:15 a.m. Was extremely annoying. Traffic noise was little distracting. We brought a box fan so at night traffic noise was blocked out.

  • Review Submitted: Oct 23, 2016
  • Date of Stay: Oct 2016
  • Source: HomeAway
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0 0

Wonderful vacation

  • 5 of 5

Check in was very easy. Any problems were taken care of quick. The Condo was very spacious. Easy walk to the beach which is amazing. The pool was large and lots of places to relax . Great vacation!! Thank you

  • Review Submitted: Apr 26, 2016
  • Date of Stay: Apr 2016
  • Source: VRBO, from HomeAway
Did you find this review helpful?
0 0


  • 5 of 5

Property was clean and we'll kept. Quite and relaxing. Condo was updated with plenty of room. I would recommend this condo and property to anyone looking to go to Siesta Key.

  • Review Submitted: Apr 12, 2016
  • Date of Stay: Apr 2016
  • Source: VRBO, from HomeAway
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0 0


Siesta Key Beach
"Rated the best in America by Dr. Beach in 2011 "Siesta Beach in Sarasota boasts that it has..."
Captain Curt's Crab & Oyster Bar
"Great food. Family friendly by day and a fun backroom saloon by night. Curt's is renown for ..."
Ophelia's on the Bay
"Pricey, but worth it. Magnificent seafood and a incredible setting. Treat yourself!"
St. Armands Circle Park
"Great change of pace for excellent shopping and dining experiences. "
The Cottage Restaurant
"Quaint little restaurant with terrific food, cocktails, and live entertainment. "
Clayton's Siesta Grille
"Only a short walk to a great dining experience and one of the most friendly atmospheres on t..."
Lobster Pot Restaurant
"For a true New England seafood experience not available anywhere else in the Sarasota area. "
Sarasota Jungle Gardens
"For young children, this is a great little zoo where you can interact with the animals and a..."
Ed Smith Stadium
"For baseball fans, Baltimore Orioles spring training and Grapefruit League at Ed Smith Stadi..."
The Broken Egg -- CLOSED
"A Siesta Key institution. Super tasty breakfast cuisine with lots of healthy options too!"
Crescent Beach Grocery
"The friendly staff will help you find anything needed for your visit to Siesta Key. No need ..."
Nearest Airport
12.5 Miles
Sarasota-Bradenton International Airport
Nearest Barpub
100 Metres
Sniki Tiki
Nearest Motorway
6 Miles
Nearest Restaurant
200 Metres
Captain Curts
Nearest Beach
200 Metres
Siesta Key Crescent Beach
Car: not necessary

Outdoor activities abound in this area of the Key. 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.


Prices & Availability

Prices for this holiday condo in the Siesta Key, Florida

Rental Basis:
per property
Owner accepts payment in:
Convert Currency
Rental Period Minimum Price Additional Nights Weekend Night Weekly Monthly * Event Price
Peak Season 2017
15 Jan 2017 - 28 Apr 2017
7 night minimum stay
for 7 nights
Summer Season 2017
29 Apr 2017 - 29 Sep 2017
Changeover Day: Saturday
7 night minimum stay
for 7 nights
Fall Season 2017
30 Sep 2017 - 17 Nov 2017
Changeover Day: Saturday
7 night minimum stay
for 7 nights
Holiday Season 2017
18 Nov 2017 - 12 Jan 2018
Changeover Day: Saturday
7 night minimum stay
for 7 nights
Peak Season 2018
13 Jan 2018 - 27 Apr 2018
Changeover Day: Saturday
7 night minimum stay
for 7 nights

Additional pricing information

Refundable Damage Deposit £322
Tax Rate 12.0%

For the convenience of our guests, there are no cleaning or booking fees
5% discount to repeat guests and active Service personnel
Check-in day for rentals is Saturday with exceptions for multi-week rentals.

Owner's Cancellation Policy

Please ask the owner or check their rental agreement when booking the property.
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