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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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Reviews

7.8 out of 10

Good

4 bedrooms2 bathroomsSleeps 82800 sq ft

Popular amenities

  • Parking available
    Parking available
  • Pet-friendly
    Pet-friendly
  • Washer
    Washer
  • Kitchen
    Kitchen
  • Air conditioning
    Air conditioning
  • Dryer
    Dryer

Explore the area

Map
Anna Maria, FL
    Bradenton Beach
    6 min walk
    Palmetto Avenue Beach
    7 min walk
    Island Players
    9 min walk
    Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
    32 min drive

Rooms & beds

4 bedrooms (sleeps 8)

King Bedroom 1, TV, Ensuite, 3rd Floor

Queen Bedroom 1, TV, 2nd Floor

Queen Bedroom 2, TV, 2nd Floor

Queen Bunk Bedroom, TV, 2nd Floor

2 bathrooms

Guest Bathroom, 2nd Floor

Bathtub or shower · Toilet

King Bathroom 1, Ensuite, 3rd Floor

Bathtub · Toilet · Shower only

Spaces

Kitchen
Dining
Living area
Exterior

About this property

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.

Property manager

Anna Maria Life Vacation Rentals
Premier Host

Languages

English

Amenities

Pool
Kitchen
Washer
Dryer
Pet-friendly
Free WiFi

Similar properties

Nirvana:Pool & Hot Tub, Dock, On Canal with Gorgeous Water Views by Anna Maria Life Vacation Rentals
Pool
Hot tub
Kitchen
Washer
9.8 out of 10, (17 reviews)
Nirvana:Pool & Hot Tub, Dock, On Canal with Gorgeous Water Views by Anna Maria Life Vacation Rentals

House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM

Children

Children allowed: ages 0-17

Events

No events allowed

Pets

Pets allowed

Smoking

Smoking is not permitted

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

About the area

Anna Maria

Located in Anna Maria, this vacation home is near theme parks and on the waterfront. The area's natural beauty can be seen at Bradenton Beach and Anna Maria Beach. Traveling with kids? Consider AMI Paddleboard Adventures, or check out an event or a game at LECOM Park. Be sure to check out the area's animals with activities such as game walks and birdwatching.
Map
Anna Maria, FL

What's nearby

  • Bradenton Beach - 6 min walk
  • Anna Maria Island Museum and Historical Park - 13 min walk
  • Anna Maria City Pier - 19 min walk
  • Anna Maria Beach - 4 min drive
  • Bean Point Beach - 4 min drive

Getting around

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

Restaurants

  • ‪Anna Maria Island Beach Cafe - ‬5 min drive
  • ‪Rod & Reel Pier - ‬4 min drive
  • ‪Sandbar Seafood & Spirits - ‬10 min walk
  • ‪Two Scoops - ‬18 min walk
  • ‪The Waterfront Restaurant - ‬18 min walk

Reviews

7.8

Good

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 11 out of 24 reviews" "
Rating 8 - Good. 6 out of 24 reviews" "
Rating 6 - Okay. 3 out of 24 reviews" "
Rating 4 - Poor. 1 out of 24 reviews" "
Rating 2 - Terrible. 3 out of 24 reviews" "

8.2/10

Cleanliness

8.8/10

Check-in

9.0/10

Communication

9.4/10

Location

8.8/10

Listing accuracy

Reviews

This review comes from a trusted partner site and has not been verified.

10/10 Excellent

5 Stars
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!
This review comes from a trusted partner site and has not been verified.

8/10 Good

Sheryl H.

216 Chillson
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.
This review comes from a trusted partner site and has not been verified.

6/10 Okay

Scott G.

3 Stars
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.
This review comes from a trusted partner site and has not been verified.

6/10 Okay

Scott G.

3 Stars
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.

8/10 Good

James M., Wrentham, MA

Liked: Cleanliness, communication, location, listing accuracy
Disliked: Check-in
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, check-in, communication, location, listing accuracy
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
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Jesse S., Charlotte, NC

Great home with everything you need!
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.

10/10 Excellent

Emily H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Ashton C.

5 Stars
Lovely house, very clean, amazing view, all the amenities and more! We will definitely be back!
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Ashwin V.

Amazing house
Fantastic house with a great pool. Rooms are big and AC works really well in the heat. Only 2 bathrooms and not a lot of accessories in the bathrooms - minor issue but nothing huge

10/10 Excellent

Melissa C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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, check-in, communication, location, listing accuracy
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, check-in, communication, location, listing accuracy
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
This review comes from a trusted partner site and has not been verified.

8/10 Good

Vicki D.

5 o'clock somewhere
We really did enjoy this house at 5 o'clock somewhere the kitchen was fully equipped and I had enough bedrooms. We knew going it only had two bathrooms and we worked everything out for the three bedrooms with only one bathroom the only thing I would suggest about the home is that they need to put TVs in the two bedrooms that do not have them. Other than that it was a great home and we enjoyed it very much
This review comes from a trusted partner site and has not been verified.

4/10 Poor

Molly S.

Check in yourself...
Hello, If you would like to know how this home rents I suggest you go check in and stay for a few nights yourself. I have rented 5-6 homes on AMI over the past 10 years and this one for the price was the worst. The home smelt the minute we walked in. The pool area and garage needed a good power wash. There were minimal outdoor chairs. The pool was not serviced and not heating. We had to dig in the closets for clean pillowcases through trash bags. The master dresser was broken, the master patio chair was broken, the master toilet seat broke. The family room furniture was stained and the carpet is in desperate need of cleaning or replacing. When we had to use the vacuum it was filthy and made the house smell even worse. When I called your office they tried to tell me that's how it is living on the island. Well, I have visited multiple times and other homes do not smell musty and owners usually care enough to keep up with their homes to continue to get returning customers. Clearly these owners do not care enough to put any money into upkeep and as a company you should consider breaking ties with them until they do. Does not look good for you. Take it or leave it, just feedback.
This review comes from a trusted partner site and has not been verified.

2/10 Terrible

Thomas D.

Utterly Disappointing
We have rented 3 homes on AMI and stayed at others with friends. This one was by far our least favorite. Firstly, the door handle to the entrance fell off when opened the first time...this was AFTER the combination did not work and we were lucky enough to to find an open door off the deck. Secondly, the back of the combination pad fell off and we couldn't get to stay on. Maintenance came and taped it back on. The lights in the TV area off the pool were ALL out. MOST importantly the hot tub did not work. We notified management within an hour of arrival to let them know. We did not get a response that day nor on Sunday. Called back on Sunday....we told they couldn't get anyone out. No call back on Monday...called again...Bev with the management company seemed to find it humorous as she laughed throughout our conversation only to giggle that she “must be distracted. No fix Monday. Tuesday called again and they sent the handyman...WHO DOES NOT MAINTAIN POOLS!!! Wednesday called again and finally someone got it to limp along until Saturday. And I say limp because it still only worked sporadically. Pool, Hot tub and whole outdoor area were in need of a good power wash. We would have done it ourselves just to have it cleaned. Dresser in master bedroom broken and drawers literally all unusable as they fall out when pulled even inches. Honestly the list can go on and on. Wayyyyy better places to spend $6200 on AMI. Unless you are looking to spend that kind of money on a state of the art toaster...that worked beautifully.
This review comes from a trusted partner site and has not been verified.

2/10 Terrible

Thomas D.

Utterly Disappointing
We have rented 3 homes on AMI and stayed at others with friends. This one was by far our least favorite. Firstly, the door handle to the entrance fell off when opened the first time...this was AFTER the combination did not work and we were lucky enough to to find an open door off the deck. Secondly, the back of the combination pad fell off and we couldn't get to stay on. Maintenance came and taped it back on. The lights in the TV area off the pool were ALL out. MOST importantly the hot tub did not work. We notified management within an hour of arrival to let them know. We did not get a response that day nor on Sunday. Called back on Sunday....we told they couldn't get anyone out. No call back on Monday...called again...Bev with the management company seemed to find it humorous as she laughed throughout our conversation only to giggle that she “must be distracted. No fix Monday. Tuesday called again and they sent the handyman...WHO DOES NOT MAINTAIN POOLS!!! Wednesday called again and finally someone got it to limp along until Saturday. And I say limp because it still only worked sporadically. Pool, Hot tub and whole outdoor area were in need of a good power wash. We would have done it ourselves just to have it cleaned. Dresser in master bedroom broken and drawers literally all unusable as they fall out when pulled even inches. Honestly the list can go on and on. Wayyyyy better places to spend $6200 on AMI. Unless you are looking to spend that kind of money on a state of the art toaster...that worked beautifully.

6/10 Okay

Olivia M.

Liked: Check-in, communication, location, listing accuracy
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, check-in, location, listing accuracy
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, check-in, communication, location, listing accuracy
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, check-in, communication, location, listing accuracy
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, check-in, communication, location, listing accuracy
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.

Liked: Check-in, communication, location, listing accuracy
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

About the host

Hosted by Anna Maria Life Vacation Rentals

Host profile image
Family-owned and operated, Anna Maria Life Vacation Rentals offers everything you are looking for in an Anna Maria Island vacation rental company – exceptional properties and quality service with a personal touch. Whether it's a family vacation or a romantic getaway, AMLVR has something for everyone. From beachfront to bayside, you can choose from a quaint one-bedroom cottage, a waterfront condo with stunning views of the Gulf of Mexico, or a luxury six-bedroom pool home. AMLVR's vacation rentals offer authentic island living in paradise!

Languages:

English

Premier Host

They consistently provide great experiences for their guests