House in Anna Maria Island, FL
8 guests · 4 bedrooms · 2 baths
Reasons to book
Great for petsBring all your friends and family, even the furry ones
Top-tier experienceA high end property in this area
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental
About this house rental
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.
Amenities at 5 O'Clock Somewhere: Dog Friendly Canal Front, Elevator, Pool, Beach 2 Blocks by Anna Maria Life
Non-smoking
Pets allowed
Family friendly
Map of Anna Maria Island, FL
Ratings and reviews
10 / 10Outstanding·Jan 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.
10 / 10Outstanding·Apr 2024
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!
8 / 10Excellent·Feb 2023
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.
6 / 10Average·Jan 2023
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.
$$$$
Top rated by guests
8Excellent
(26 Ratings)
"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 rea..."
Rebecca S.Don't miss out! Price and availability may change
