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Overview
Amenities
Policies
Location
Host

7.8

Good

4 bedrooms2 bathroomsSleeps 82800 sq ft

Popular amenities

Pool

Washer

Pet-friendly

Kitchen

Air conditioning

Dryer

Explore the area

Anna Maria, FL

Anna Maria City Pier19 min walk
Anna Maria Beach4 min drive
Bean Point Beach4 min drive
Tampa, FL (TPA-Tampa Intl.)66 min drive

Most relevant reviews

8/10 Good

We love this property and it is our second year to spend January here. Unfortunately, there was quite a bit of wear and ...

Sheryl H.

Feb 3, 2023

Rooms & beds

4 bedrooms (sleeps 8)

King Bedroom 1, TV, Ensuite, 3rd Floor

1 King Bed

Queen Bedroom 1, TV, 2nd Floor

1 Queen Bed

Queen Bedroom 2, TV, 2nd Floor

1 Queen Bed

Queen Bunk Bedroom, TV, 2nd Floor

2 Single Bunk Beds

2 bathrooms

Guest Bathroom, 2nd Floor

Bathtub or shower · Toilet

King Bathroom 1, Ensuite, 3rd Floor

Bathtub · Toilet · Shower only

Spaces

Deck or patio

Porch or lanai

Kitchen

Balcony

Garden

Dining Area

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.

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

Pool

Kitchen

Washer

Dryer

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

On-site parties or group events are strictly prohibited

Host has indicated that there is a carbon monoxide detector on the property

Host has indicated that there is a smoke detector on the property

Safety features at this property include a fire extinguisher and a deadlock

About the area

Anna Maria

Located in Anna Maria, this holiday home is near theme parks and on the waterfront. The area's natural beauty can be seen at Bean Point Beach and Anna Maria Beach. Travelling with kids? Consider AMI Paddleboard Adventures, or check out an event or a game at LECOM Park. Make sure you get close to the area's animals with activities such as game walks and birdwatching.

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, FL (SRQ-Sarasota-Bradenton Intl.) - 32 min drive

Restaurants

‪Anna Maria Island Beach Cafe - ‬5 min drive
‪The Waterfront Restaurant - ‬18 min walk
‪Sandbar Seafood & Spirits - ‬10 min walk
‪The Ugly Grouper - ‬4 min drive
‪Harry's Grill - ‬7 min walk

Frequently asked questions

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

Yes, pets are allowed at this property.

What time is check-in at 5 O'Clock Somewhere: Dog Friendly Canal Front, Elevator, Pool, Beach 2 Blocks by Anna Maria Life?

Check-in begins at 4:00 PM.

What time is check-out at 5 O'Clock Somewhere: Dog Friendly Canal Front, Elevator, Pool, Beach 2 Blocks by Anna Maria Life?

Checkout is at 10:00 AM.

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

This family-friendly Anna Maria holiday home is located on the waterfront, within a 10-minute walk of Bradenton Beach, Palmetto Avenue Beach and Island Players. Bay Boulevard Beach and Historic Green Village are also within 1 mile (2 km).

7.8

Good

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.

Learn more

8.2/10

Cleanliness

8.8/10

Check-in

9.0/10

Communication

9.4/10

Location

8.8/10

Listing accuracy

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

10/10 Excellent

9 April 2024

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.

3 February 2023

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.

16 January 2023

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.

15 January 2023

3 Stars

8/10 Good

James M., Wrentham, MA

24 October 2022

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

About the host

Hosted by Anna Maria Life Vacation Rentals

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!