5 O'Clock Somewhere: Dog Friendly Canal Front, Elevator, Pool, Beach 2 Blocks by Anna Maria Life

Anna Maria, Florida
$622 avg/night
Bed 4

Bed

Bath 2

Bath

Home Private Vacation Home

Property Type

Sleep 8

Max Sleeps

5 O'Clock Somewhere by Anna Maria Life Vacation Rentals
216 Chilson, Anna Maria, FL 34216

What You'll Love About This Home:
Location! 2 Blocks to the Beach & On a Canal!
4 Bedrooms / 2 Bathrooms
1 King, 2 Queens, Queen over Queen Bunkbeds
Private Heated Pool & Spa
Pool Loungers & Umbrellas
Poolside Cabana Room with Lounge Furniture, Dining Table & TV
Outdoor Shower
Gas Grill
Elevator (see notes about deposit)
Private Boat Dock (boat liftis not available)
Ping Pong Table
Professional Linen Service, Washer & Dryer
Complimentary WIFI
Dog Friendly - with pet fee - see info below
Beach Towels, Beach Chairs, Beach Wagon
Parking for 4 Cars

Details:
Located two blocks from the beach and on a canal with a boat dock, 5 O'Clock Somewhere offers the ultimate relaxation amongst the natural beauty of Anna Maria Island!

The main living area on the second level features an open kitchen with a wine fridge and breakfast nook providing plenty of space to make your favorite meals. The dining table seats eight with additional seating at the kitchen island. Patio doors to a furnished verandah fill the rooms with sunshine. Unwind on one of the cushy sofas or flip on the TV while you cook breakfast in the morning.

Three of the bedrooms are located on this level; two with queen beds and the third with a set of queen over queen bunkbeds. The third floor is home to the master bedroom which features a king size bed, ensuite bathroom and private deck overlooking the pool and canal. Each bedroom has a TV and guests will enjoy crisp sheets and fluffy towels from our professional linen service. Your guests will stay connected with complimentary WIFI and enjoy all of the comforts of home, including a washer and dryer.

The pool level features an indoor cabana room, furnished with lounge seating, TV and dining table for six. Guests will enjoy the ping pong table. Step outside into the lush backyard with a private heated pool and jacuzzi. Other highlights include a grill, pool loungers, and canal views. An outdoor shower with hot and cold water allows you to rinse the sand from your suit before entering the pool.

Bring the boat! The boat dock is available for your boat and you're just minutes away from the open waters of Bimini and Tampa Bay! (Please note the boat lift is not available.)

If you would like use of the elevator, please contact our office A $500 fully refundable security deposit is required.

5 O'Clock Somewhere is a dog friendly home! 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. Please note, there is a 2-dog limit

5 O'Clock Somewhere is easy walking distance to Gulf Ave, restaurants, and the free island trolley, which travels the entire length of the 7 miles of the island. Hop on and off at your leisure and explore shopping, dining and the beaches. The perfect location for your next beach vacation!

Bedroom 1 - King Bed, Ensuite Bathroom, TV - Floor 3
Bedroom 2 - Queen Bed, TV - Floor 2
Bedroom 3 - Queen Bed, TV - Floor 2
Bedroom 4 - Queen over Queen Bunkbeds, TV - Floor 2

Please note:
Elevator is available with a $500 fully refundable security deposit. Please contact our office.
Boat Lift is not for guest use.
Amenities are subject to change.

DISCLAIMER: Depth of the canals and channels vary depending on tides, weather, and other circumstances beyond our control. At times this can result in a water level that is too low to support watercraft. It is the responsibility of the guest to review forecasts and make alternate arrangements for watercraft as necessary.

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.

VR18-000132

IMPORTANT INFORMATION:

Your booking is with Anna Maria Life Vacation Rentals. We will send you check-in instructions 14 days prior to your arrival date. We will send you our rental agreement in an electronic signature document. Please review and return to us by following the instructions.

** Your signed rental agreement must be returned in order to receive your check-in details.

VRBO BOOKINGS

Anna Maria Life Vacation Rentals will charge your credit card for your deposit payment. You will also see a separate charge by VRBO for their service fee.

Your final balance is due 60 days prior to your arrival date. We will send you a final payment reminder 90 days prior to arrival. We do not automatically charge your card for your final balance.

The instructions for making your final payment will be included in your final payment reminder.

Please review the cancellation policy prior to booking.

GOOGLE VACATION RENTAL BOOKINGS

Your payment is due in full at the time of booking and the final balance information above does not apply to your reservation.

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  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • PETS

    Pet Friendly
  • BEACH

    Near The Beach
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Deadbolt Lock Fire Extinguisher Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    4 Bedrooms Bed Sheets Provided
  • GENERAL

    Unit Size: 2800 Sq Ft (260 Sq M)
  • KITCHEN

    Coffee/tea Maker Cookware/dishes/utensils Dishwasher Kitchen Island Microwave Oven Refrigerator Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Onsite Parking
  • INTERNET

    Free WiFi
  • OUTDOORS

    Balcony Barbecue Grill Dock Garden
  • POOL/SPA

    Heated Pool Private Pool
  • BATHROOMS

    2 Bathrooms Bathtub Or Shower Hair Dryer Towels Provided
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Birdwatching Nearby Casino Nearby Ecotours Nearby Golfing On Site Hiking/biking Trails Nearby Mountain Biking Nearby Power Boating Nearby Water Skiing Nearby Wildlife And Game Walks Nearby Winery Tours Nearby
  • ENTERTAINMENT

    Arcade/game Room DVD Player Table Tennis Smart TV With Cable/satellite Service
  • LIVING SPACES

    Living Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • LOCATION HIGHLIGHTS

    Near A Hospital Near A Zoo Near Outlet Shopping Near The Bay Near The Sea On The Waterfront
  • SERVICES AND CONVENIENCES

    Iron/ironing Board Phone
  • SUITABILITY/ACCESSIBILITY

    Elevator Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 8

Map Map

School District Rates & Availability

Review Review

  • Rebecca S.

    Submitted Jan 24, 2026

    Stayed Jan 17, 2026

    Amazing house, looks just like the photos, ignore the meh comments from 2-3 years ago it’s now managed by Anna Maria Life Rentals who we found to be awesome, very responsive. Pool and hot tub (yes real hot tub not just a spa!) were not quite working when we got there but they jumped on it. We had a great time, walkable to nearby restaurants (The Porch - yum - hit happy hour for 1/2 price bottle of wine to go with fabulous dinner) and sunsets. Wonderful house, quiet side street, five stars. Would definitely return.

  • Submitted Apr 9, 2024

    Stayed Dec 31, 1969

    5 O'Clock Somewhere is the perfect vacation rental! The house is beautifully decorated, very clean, and spacious. We spent a lot of time downstairs in the tv/game rooms and pool area. The backyard is an amazing tropical oasis. Perfect for playing in the pool, sitting in the jacuzzi, or laying out in the warm FL sun. The house provided pool toys, beach items, and fishing poles. Even though we didn't catch fish from the dock, we had lots of fun trying. I would highly recommend this location for your next getaway! We can't wait to visit again!

  • Sheryl H.

    Submitted Feb 3, 2023

    Stayed Dec 31, 1969

    We love this property and it is our second year to spend January here. Unfortunately, there was quite a bit of wear and tear in the last year. All of our concerns were immediately addressed with the exception of loss shower floor tiles and the microwave was not working. Substantial rent increases will be a problem.

  • Scott G.

    Submitted Jan 16, 2023

    Stayed Dec 31, 1969

    When we arrived at the house, the internal temperature was 55 degrees, very cold, and it took hours to heat up. The pool heater and spa pump did not work when we arrived. It took several days for the repairs and then for the pool to heat up to a usable temperature. The grill and grill tools were so old and dirty it was almost unusable. Several of the door alarms had been disabled (we did not do it!). Kitchen baking trays were dirty. The pool deck was dirty. And when I opened a window, the window frame and screens were very dirty. Overall, disappointed.

  • Scott G.

    Submitted Jan 15, 2023

    Stayed Dec 31, 1969

    When we arrived at the house, the internal temperature was 55 degrees, very cold, and it took hours to heat up. The pool heater and spa pump did not work when we arrived. It took several days for the repairs and then for the pool to heat up to a usable temperature. The grill and grill tools were so old and dirty it was almost unusable. Several of the door alarms had been disabled (we did not do it!). Kitchen baking trays were dirty. The pool deck was dirty. And when I opened a window, the window frame and screens were very dirty. Overall, disappointed.

  • James M.

    Submitted Oct 24, 2022

    Stayed Oct 15, 2022

    We've vacationed at AMI multiple times and love the canal side locations - so close to the beach (3 minute walk) and still waterfront with a pool. This was our first stay in this property. The home is wonderfully decorated and the layout is great for families with a large open floor plan and a very nice ground level patio entertainment space. The pool is great and the hot tub works wonderfully, we even fished (fishing rods provided!) and caught salt water catfish. The management company was very responsive when we called with issues and solved most of them right away, thanks to them for their prompt service! A few challenges remain for this to be representative of a $6K - $7K weekly rental. 1. Nearly all of the outside lights don't work (burned out we assume) so lighting is an issue, makes it tough to use the grill at night for example 2. The hot tub light is burned out as are most of the landscaping lights 3. The boards on the canal decking need to be sanded/refinished. Several kids got nasty splinters 4. Not enough outside furniture for a home that sleeps 8-10 people. Only 2 lounge chairs at the pool, seating for 3 on the main deck 5. Several of the doors don't shut all the way without a deadbolt. This causes the door alarms to sound when the wind blows, very annoying 6. There is no cable TV that we can find - so you have to have a streaming service to watch live sports or any TV at all really. Plus the TV systems have no instructions so you're guessing. None of the remote controls had batteries upon arrival, management company fixed this the next day 7. Labeling the light switches would be a plus - there are so many that it took several days to figure it all out. Same with the hot tub - instructions for all the buttons 8. The beds and most especially the pillows need to be replaced. Pillows are essentially like sleeping with no pillow at all. When we arrived half the beds had no pillows and the ones that did didn't have enough pillow cases to cover - the management company responded right away the next day to fix this Overall a wonderful stay yet again on AMI - the house could use some small updates or upgrades or maintenance to be on par with its price. Some of the stuff is so easy to fix, just a little more attention would catch it all.

  • Katherine R.

    Submitted Oct 18, 2022

    Stayed Oct 8, 2022

    We were so glad we were able to still come despite Hurricane Ian. The property had everything my husband and I needed during our stay. We spent a lot of time in the outdoor spaces and porches. The proximity to the beach was very walkable, about 2 blocks.

  • Jesse S.

    Submitted Sep 7, 2022

    Stayed Dec 31, 1969

    5 O'Clock Somewhere is an awesome vacation rental that has everything you need for your beach vacation. The updates inside are very nice and the hardwood style floors throughout were a big plus. Our family of four and two dogs absolutely loved the house and the outdoor space. Dogs enjoyed soaking up the sun on their beds by the pool while we enjoyed drinks and snacks in the covered cabana. Anna Maria Life is one of the only agencies without a breed restriction and for that you have gained a loyal family of customers already planning our next trip.

  • Emily H.

    Submitted Sep 2, 2022

    Stayed Aug 20, 2022

    The property was great and had more than enough space for our whole family. Will stay again. Thank you so much!

  • Ashton C.

    Submitted Aug 20, 2022

    Stayed Dec 31, 1969

    Lovely house, very clean, amazing view, all the amenities and more! We will definitely be back!

Your dates are Available!

Total

Includes taxes and fees
$622+
View details