5 O'Clock Somewhere

  • 4 Beds |
  • 2 Baths |
  • 8 Guests

5 O'Clock Somewhere

5 O'Clock Somewhere
216 Chilson Ave, Anna Maria, FL 34216

What You'll Love About This Home:

  • Location! North End of AMI - 2 Blocks to the Beach & On a Canal
  • 4 Bedroom / 2 Bathroom
  • Elevated Home with Elevator (see deposit notes)
  • 1 King, 2 Queens, 1 Set of Queen over Queen Bunkbeds
  • Private Heated Pool & Spa
  • Outdoor Shower
  • Poolside Cabana Room 
  • Gas BBQ Grill
  • Professional Linen Service, Washer & Dryer, Complimentary WIFI
  • Beach Wagon, Chairs & Towels
  • Dog Friendly (see below)
  • Private Boat Dock (boat lift is not available)
  • 4 Parking Spaces


As the name would suggest, our property 5 O'Clock Somewhere is all about indulging in ultimate relaxation and soaking up the natural beauty of Anna Maria Island! Located only two blocks from the beach, this property is also located along a canal, giving you the best of both waterfronts. Bring your favorite beach gear, and even your boat—docking is one of the many amenities this property has to offer! 

When you drive up to this home, you’ll immediately notice the gorgeous landscaping, with trimmed palms and a perfectly manicured lawn. Enter the home and journey up to the main level, where you’ll arrive at a modern open concept space with the living area and kitchen. Nautical inspired décor meets a sleek minimalistic style, creating a calm and blissful place to sit back and relax. Unwind on one of the cushy sofas, or flip on the TV while you cook breakfast in the morning. 

For those who like to make a fun event out of vacation dinners, the fully equipped kitchen will cover all your cooking needs, with state-of-the-art appliances and generous amount of counterspace. An elegant dining table seats up to eight, and the kitchen island has six seats, making it a great place to enjoy a quick snack or bite to eat before you head out to explore the beach. Just outside a pair of French doors, you’ll find a lovely little balcony. 

Four bedrooms make this property great for big family vacations or trips with groups of friends. Two bedrooms are furnished with queen beds and one bedroom has a set of queen over queen bunkbeds. The master occupies an entire level of its own, offering a sense of luxury and privacy with a king-sized bed, spa-like bathroom, and private deck. 

Downstairs there is a cabana room, furnished with comfortable seating and a TV where you can sit back and put on the day’s game. This space opens into the lush backyard, which features a private heated pool and jacuzzi. Other highlights include a BBQ grill, lounge chairs, and canal views. There’s an outdoor shower for rinsing off after an afternoon at the beach, which is just another added luxury to this already fantastic property! 

Nearby you’ll find a stop for the free Anna Maria Island trolley, which can take you to further beaches, restaurants, and shops. You’re never far from dining, lovely nature, and entertainment when you stay at this property and relaxation is always on the agenda because it’s always 5 O'clock somewhere! 

There is a fully refundable $500.00 Deposit for use of the Elevator. If you are booking online and would like use of the elevator during your stay please contact us after booking so that we can add the Elevator Deposit to your reservation. 

5 O'Clock Somewhere is a dog-friendly property! If you have added a pet to your reservation under the number of pets, the fee of $150 per dog, plus tax has been added to your reservation total. ** 2 Dog Limit **

*No Cats Allowed Due To Allergy Concerns.

You are vacationing in a residential area.  Please be a good neighbor by keeping the noise to a respectful level during the day and night.  Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property



Enhanced Cleaning Practices
Pet Friendly
Single Family Homes
Anna Maria
Boat Dock Available
Canal Front
Ping Pong Table
Parking space
Short Walk To The Gulf
Water View
  • Checkin Available
  • Checkout Available
  • Not Available
  • Available
  • Checkin Available
  • Checkout Available
  • Not Available

Seasonal Rates (Nightly)


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5 O'Clock Somewhere

  • 4 Beds |
  • 2 Baths |
  • 8 Guests

including taxes and fees
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Secure Booking Experience
(15 reviews)
  • Sleeps: 8
  • Bedrooms: 4
  • Bathrooms: 2
  • Pets: 2