Entire home
5 O'Clock Somewhere: Dog Friendly Canal Front, Elevator, Pool, Beach 2 Blocks by Anna Maria Life
Waterfront holiday home with private pool and kitchen
Photo gallery for 5 O'Clock Somewhere: Dog Friendly Canal Front, Elevator, Pool, Beach 2 Blocks by Anna Maria Life





Reviews
7.8 out of 10
Good
4 bedrooms 2 bathrooms Sleeps 8 2800 sq ft
Popular amenities
Explore the area

Anna Maria, FL
- Place, Anna Maria City Pier14 min walk
- Place, Bean Point Beach3 min drive
- Place, Anna Maria Beach4 min drive
- Airport, Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)39 min drive
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.
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.
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.
Add dates for prices
Amenities
Pool
Kitchen
Washing machine
Dryer
Pet-friendly
Free WiFi
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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 Fish Hole Adventure Golf, 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
- Anna Maria Island Museum and Historical Park - 11 min walk - 0.9 km
- Anna Maria City Pier - 14 min walk - 1.2 km
- Bradenton Beach - 14 min walk - 1.2 km
- Bean Point Beach - 3 min drive - 1.7 km
- Anna Maria Beach - 4 min drive - 2.4 km
Getting around
Restaurants
- 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
- North Shore Cafe - 11 min walk
Frequently asked questions
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!
Languages:
English
Premier Host
They consistently provide great experiences for their guests
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