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

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Fridge, microwave, oven, stovetop
A heated pool
Dining
Terrace/patio
Interior

Reviews

8.0 out of 10
Very good

Entire home

4 bedrooms2 bathroomsSleeps 8260 sq m

Popular amenities

  • Pool
  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly
  • Free Wi-Fi

Explore the area

View map
Anna Maria, FL
  • Place, Bradenton Beach
    ‪6 min walk‬
  • Place, Island Players
    ‪11 min walk‬
  • Place, Bean Point Beach
    ‪2 min drive‬
  • Airport, Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
    ‪45 min drive‬

Room options

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  • Washing machine
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About the area

Anna Maria

When you stay at this vacation home in Anna Maria, you'll be on the waterfront, within a 5-minute drive of Bean Point Beach and Anna Maria Beach. .This vacation home is 13.1 mi (21.1 km) from IMG Academy and 23.1 mi (37.1 km) from Tampa Bay.
View more Holiday homes in Anna MariaOpens in a new window

What's nearby

  • Bradenton Beach - 6 min walk - 0.6 km
  • Palmetto Avenue Beach - 6 min walk - 0.6 km
  • Island Players - 11 min walk - 0.9 km
  • Anna Maria Island Museum and Historical Park - 14 min walk - 1.2 km
  • Bean Point Beach - 2 min drive - 1.7 km

Getting around

  • Sarasota-Bradenton Intl. Airport (SRQ) - 32 min drive

Restaurants

  • ‪Anna Maria Island Beach Cafe - ‬7 min drive
  • ‪The Ugly Grouper - ‬4 min drive
  • ‪The Sandbar Restaurant - ‬10 min walk
  • ‪The Waterfront Restaurant - ‬18 min walk
  • ‪Ginny's & Jane E's - ‬7 min walk

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

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

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 lift is 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.
Make yourself comfortable in this air-conditioned vacation home, which features a private pool and a Smart TV. There's a private balcony. A kitchen is outfitted with a refrigerator, an oven, and a stovetop. Complimentary wireless internet access keeps you connected, and a DVD player is provided for your entertainment.
Take in the views from a garden and make use of amenities such as an arcade/game room and barbecue grills.
Featured amenities include laundry facilities and an elevator.

Property amenities

Beach

  • Beach nearby

Pool/Spa

  • Heated pool
  • Private pool

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Hob
  • Kitchen island
  • Microwave
  • Oven
  • Refrigerator
  • Toaster

Dining

  • Dining table

Bedrooms

  • 4 bedrooms
  • Bedsheets provided

Bathroom

  • 2 bathrooms
  • Bathtub
  • Bathtub or shower
  • Hair dryer
  • Shower
  • Towels provided

Living spaces

  • Dining table
  • Living room

Entertainment

  • DVD player
  • Smart TV with cable/satellite channels

Outdoor areas

  • Balcony
  • Barbecue grill
  • Dock
  • Garden

Laundry

  • Laundry facilities
  • Washer/dryer

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly

Suitability/Accessibility

  • Lift
  • Smoke-free property

Services and conveniences

  • Iron/ironing board
  • Phone

Location highlights

  • Near a hospital
  • Near a zoo
  • Near an outlet shopping centre
  • Near the bay
  • Near the marina
  • Near the sea
  • On the waterfront

Things to do

  • Arcade/game room
  • Golf
  • Heated pool
  • Table tennis
  • Basketball nearby
  • Birdwatching nearby
  • Casino nearby
  • Ecotours nearby
  • Fishing nearby
  • Golfing nearby
  • Hiking/biking trails nearby
  • Horseback riding nearby
  • Jet skiing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Mountain biking nearby
  • Parasailing nearby
  • Rafting nearby
  • Sailing nearby
  • Scuba diving nearby
  • Snorkelling nearby
  • Surfing/bodyboarding nearby
  • Swimming nearby
  • Theme park nearby
  • Water skiing nearby
  • Water tubing nearby
  • Wildlife walks nearby
  • Windsurfing nearby
  • Winery tours nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher
  • Deadbolt lock

General

  • Garden
  • Unit size: 2,800 square feet

Policies

Check-in

Check-in time starts at 4:00 PM

Contactless check-in available

Minimum check-in age: 25

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Information provided by the property may be translated using automated translation tools

Pets

Pets allowed

Service animals are welcome, and are exempt from fees

Children and extra beds

Children are welcome

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadbolt lock
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

Property is also known as

5 O'Clock Somewhere Coastal Cottages

Dog Friendly Canal Front Pool Home 2 Blocks From The Beach!

Dog Friendly Canal Front Pool Home Just 2 Blocks From The Beach!

449557

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

Reviews

8.0

Very good

Rating 10 - Excellent. 13 out of 26 reviews
Rating 8 - Good. 6 out of 26 reviews
Rating 6 - Okay. 3 out of 26 reviews
Rating 4 - Poor. 1 out of 26 reviews
Rating 2 - Terrible. 3 out of 26 reviews

8.6/10

Cleanliness

Reviews

10/10 Excellent

Tracy B., Nantucket, MA

Liked: Cleanliness
Great house. Great management company.
Stayed 6 nights in Feb 2026

10/10 Excellent

Rebecca S., Wayland, MA

Liked: Cleanliness
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.
Stayed 7 nights in Jan 2026

8/10 Good

James M., Wrentham, MA

Liked: Cleanliness

Beautiful location and home with some challenges

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.
Stayed 7 nights in Oct 2022

10/10 Excellent

Katherine R.

Liked: Cleanliness

5’clock Somewhere

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.
Stayed 7 nights in Oct 2022

10/10 Excellent

Emily H.

Liked: Cleanliness

Had a great time with family!

The property was great and had more than enough space for our whole family. Will stay again. Thank you so much!
Stayed 7 nights in Aug 2022

10/10 Excellent

Melissa C.

Liked: Cleanliness

Amazing Place

We enjoyed our stay. Beautiful house with great view. Very spacious and lots to do.
Stayed 7 nights in Jul 2022

10/10 Excellent

Kate K., Minneapolis

Liked: Cleanliness

Perfect Vacation Rental for our family!

We loved our time at this property. The house is exactly as shown. The house is beautiful decorated, linens and towels were high quality and plentiful, house was clean and lovely. Bathrooms and kitchens were beautiful and the frame TVs added to the loveliness. We had several issues with the air conditioning during our stay and they were addressed immediately by the management company (Anna Maria Life) and followed up with by A/C company. They kept us cool despite the technical difficulties. The same was true of the couple times we couldn't get the hot tub to heat up--management company responded immediately and the pool company came twice during our stay to clean the pool. The house feels brand new and the pool area. while a bit older, was wonderful. Kids loved playing basketball, ping pong and volleyball and we loved just hanging in the beautiful yard and watching basketball from the great poolside area. Location was wonderful--close to pine, but quiet street. Great access to everything! We were very pleased with both the property and the management company. We would definitely stay at this property again.
Stayed 7 nights in Apr 2022

8/10 Good

Melissa M., Titusville

Liked: Cleanliness

Great Family Vacation

The listing is accurate. We booked our trip and then other reviews were posted that were not good. This made us very skeptical about what to find, since we couldn't change our dates, etc. The kitchen was stocked like normal rental properties. The house was clean. Location was perfect. We really enjoyed our stay. You need to be careful on the dock, as some nails are popping up and the wood is older. Pool service came twice the week we were there. We all arrived happy and left happy :)
Stayed 7 nights in Jul 2021

6/10 Okay

Olivia M.

Great location but....

This property is in a great location and it was so nice to have a dock for our boat. Having an elevator was great too. The house was cleaned but there were a bunch of things that couldn't be seen from the pictures. The couch cushions were very stained as were the pool chair cushions. I actually tried to clean the pool chairs but ended up running to Lowes and purchased new ones, red was all they had. The outdoor furniture was pretty stained too. One ottoman was totally ripped up. The stairs up to the master bedroom actually had some carpet tacks sticking up so I recommend wearing shoes. Also wear shoes on the dock as my son got a nail stuck in the bottom of his foot. The kitchen was clean but we ended up having to go buy some rocks glasses and some new kitchen knives as they were very dull and some had the tips broken off. There is also an exposed electrical socket in the bunk bed room. The first main floor toilet lifts when you is on it. There were a bunch of beach items in the garage from the previous renters that were dirty and sandy. All in all our stay was less than average but like I said it was a great location and they do accept pets. Probably wouldn't stay again though.
Stayed 14 nights in Aug 2020

8/10 Good

kim w.

Liked: Cleanliness

great trip

it was large enough for our group and had the perfect location. the pool and hot tub were great. we really appreciated the beach towels. the hot tub, unfortunately, never warmed up.
Stayed 7 nights in Jul 2020

10/10 Excellent

Greg P.

Liked: Cleanliness

Perfect Vacation in AMI

Awesome location. Great boat dock with easy access to Tampa Bay, Bean Point and Longboat Key. The pool and backyard was amazing. We will definitely be back.
Stayed 7 nights in Jun 2020

2/10 Terrible

Mark D.

Disliked: Cleanliness

This was the worst property and property Mgt co. The pool heater never worked nor did the spa .

The Mgt co claimed there had not been a dog in the house for 9 months. That was a lie. The neighbors said there are dogs there all of the time. I had to sleep on the patio outside. Sick house. Horrible Mgt co. Disputing all charges.
Stayed 10 nights in Jan 2020

10/10 Excellent

Jordan H.

Liked: Cleanliness

Great Vacation Home

Our family loved our stay at 5 O'clock somewhere. The home has a great layout with large kitchen/living room that made it a great place. The location to restaurants and the beach are great. We would definitely consider this home again in the future.
Stayed 4 nights in Aug 2019

8/10 Good

Susie A.

Minor issues/ 5 O’clock Somewhere

We had a few minor problems when we first arrived at the property (upstairs A/C wasn’t working, the driveway was filled with palm seeds that were rotting and attracting bugs/mosquitos and the hot tub was crawling with ants). However, after calling the property manager, the maintenance guy came out to access the A/C within 1/2 hour AND had a company come within 3 hours to repair it. Also, the pest control guy came to spray right away and suggested to the property manager that the lawn crew come to clean up the driveway (which they did within a few days). There are a few things that can be repaired and improved at the house. The property manager and/or the owner need to do a walk-thru and have the stains on the carpet cleaned, repair the door handle, etc. I feel that we paid A LOT to rent this house for a week and really shouldn’t have these types of issues to deal with. I realize that sometimes things happen, but the carpet stains, the loose door handle going out to the deck, the dirty couches are preventative in nature.
Stayed 7 nights in Jun 2019

10/10 Excellent

Melissa C.

Wonderful week in paradise!

Enjoyed a wonderful, relaxing, indulgent week at 5 oclock somewhere. The house was gorgeous and very comfortable. The pool, hot tub, and canal views were amazing. We will definitely be back!
Stayed 7 nights in Apr 2019

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