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

Beach paradise at the right price ** January discounts available **

Bedrooms 2
Space 1,280 sq. ft.
Property type condo
Minimum Stay 7 nights


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
Premier Partner

This partner has demonstrated and is committed to fast response times, the best rates, and a great traveler experience.

Speaks English
Response time:
Within a few hours
Response rate:
Calendar last updated:
29 November, 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 Siesta Key

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 Sarasota County

Property Type:
  • condo
  • floor 3
Building Type:
  • building
  • Self-catering
Floor Area:
  • 1280 sq. ft.
House Rules:
  • Max. occupancy: 6
  • Minimum Age Limit for Renters ...
  • children welcome
  • pets not allowed ...
  • non smoking only
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


Excellent! 4.7/5 -
(18 traveller reviews)

72% Complete
27% Complete
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Beach paradise at the right price ** January discounts available **
average rating of 4.7222223 based on 18 reviews

Great stay at a great price!

  • 5 of 5

A nice get away at a great price! We loved the pool, beach, and conveninent access to shops and restaurants. The Orange Octopus ice cream shop is a nice sweet treat just across the road. We also really enjoyed the Ringling Museum. We would also recommend Schnitzel Kitchen (delicious German food) in Sarasota!

  • Review Submitted: 03-Aug-2017
  • Date of Stay: July 2017
  • Source: HomeAway
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Orchard Park, NY

Very nice property..had all ammentities needed to enjoy a good family vacation!

  • 4 of 5

Great property, wonderful condo, great location, awesome beach, great village, free trolley, walking distance to stores, shops, groceries..I loved it!!!

  • Review Submitted: 22-Jul-2017
  • Date of Stay: July 2017
  • Source: HomeAway
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Excellent Location, Spacious Condo

  • 5 of 5

My family and I thoroughly enjoyed our stay at this property (Anchorage). The condo was clean, spacious, and equipped with everything we needed (the laundry facilities are not in-unit, but right next door in the same hall). The pool was very well-kept, and the walk to the beach was very short- only a few minutes to cross the street and head down the access. There is some traffic noise (especially noticeable at night), but the condo was located right across from restaurants and other attractions that were just a walk away. Thank you so much for sharing your beautiful condo!

  • Review Submitted: 19-Jul-2017
  • Date of Stay: June 2017
  • Source: HomeAway
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Great condo!

  • 5 of 5

Condo is gorgeous and extremley large and beautifully decorated!! Restaurant and shops near. We rented beach cruisers just cros the street Bikerental. Everything is within walking distance and the beach is just amazing.

  • Review Submitted: 31-May-2017
  • Date of Stay: May 2017
  • Source: HomeAway
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Clean condo, close to everything!!

  • 5 of 5

Siesta Chillin was the perfect stay! The condo is clean & provided everything we needed for a great week at the beach. Great restaurants, grocery store, liquor store, deli, pizza, bar, beach, pool...all within walking distance. We took the free shuttles to Siesta Villiage several times throughout the week & we had no problem getting around since we didn't have a car. I would recommend this condo to anyone looking for a very affordable getaway!

  • Review Submitted: 27-May-2017
  • Date of Stay: May 2017
  • Source: HomeAway
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Met our needs

  • 4 of 5

Nice to have beach accessories

  • Review Submitted: 02-Apr-2017
  • Date of Stay: March 2017
  • Source: VRBO, from HomeAway
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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
Holiday Season 2017
18 Nov 2017 - 19 Jan 2018
Changeover Day: Saturday
7 night minimum stay
for 7 nights
Peak Season 2018
20 Jan 2018 - 27 Apr 2018
Changeover Day: Saturday
7 night minimum stay
for 7 nights
Summer Season 2018
28 Apr 2018 - 31 Aug 2018
Changeover Day: Saturday
7 night minimum stay
for 7 nights
My Standard Rate

Changeover Day: Saturday
7 night minimum stay
for 7 nights

Additional pricing information

Refundable Damage Deposit £300.32
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.
Ask Owner a Question