Chasing Sunsets managed by Beach Retreats FL Anna Maria Island

Bradenton Beach, Florida
$878 avg/night Minimum Stay 7 Nights
Bed 4

Bed

Bath 3

Bath

Home Private Vacation Home

Property Type

Sleep 8

Max Sleeps

Night 7 nights

Min Stay

Chasing Sunsets by Beach Retreats Vacation Rentals
Holmes Beach | 4 Bedrooms | 3 Bathrooms | Sleeps 8 | Heated Pool + Spa | Elevator | Steps to the Gulf
✨ Luxury Beach Living — Just a Few Steps from the Sand ✨
Welcome to Chasing Sunsets, a stunning 4-bedroom, 3-bathroom coastal retreat located west of Gulf Drive—meaning there are no roads to cross to reach the beach. Just a 2-minute walk from the sugar-white sands of Anna Maria Island, this home offers aperfect blend of luxury, comfort, and convenience.
​​​​​​​While most of our properties rent only from Saturday to Saturday, exceptions can be made. Please reach out to us prior to booking if you would like to arrive or depart on alternate dates, or stay for fewer than 7 nights. We would love to host you!
Highlights
Less than 1 block to the Gulf beaches
2 King bedrooms, 1 Queen, 1 Bunk room (sleeps 8)
Private heated pool & spa in a tropical setting
Elevator + keyless entry for easy access
Gourmet kitchen + professional linen program
Primary suite balcony with peek-a-boo Gulf views
High-speed Wi-Fi—perfect for work or play
Pack 'n Play + high chair provided
Covered lanai with outdoor dining & lounge seating
Inside Your Home
Open-concept living area with comfortable seating + smart TV
Fully equipped kitchen with modern appliances + breakfast bar
Spacious bedrooms, each thoughtfully designed for relaxation
Private primary suite with balcony, ensuite bath, and Gulf glimpses
Professional linen program for a hotel-quality stay
Outdoor Living
Heated pool & spa surrounded by lush tropical landscaping
Large open-air decks for morning coffee or sunset cocktails
Covered lanai with plenty of shaded seating for family meals
Steps to the beach—perfect for daily dips in the Gulf
Explore Anna Maria Island
From Chasing Sunsets, you're within walking or trolley distance of island favorites:
Bean Point for tranquil beauty
Dining hotspots like The Waterfront, Chateau Anna Maria, Skinny's, and The Sandbar
Adventures like parasailing, paddleboarding, fishing, and sunset cruises
Free trolley stops nearby for easy island exploring
Booking & Cancellation
No cancellation fees!
Cancel 60+ days before arrival → Full refund
Cancel within 60 days → No refund
Extended stays & bookings $20,000+ → Full payment 90 days prior, non-refundable
$500 deposit due at booking; balance due 60 days prior
For reservations 21+ nights or $20,000+ → 10% deposit due at time of booking.
Third party travel insurance cost is due at time of purchase
Third-party travel insurance through Beach Retreats is non-refundable
No changes permitted within 60 days of arrival or during stay
We highly recommend cancelation insurance
​​​​​​​ This home can accommodate up to 3 vehicles
⚠️ Please note: The garage is reserved for owner use only and not available to guests.
⚠️ This home is located in a residential neighborhood. Please respect quiet hours and enjoy your stay responsibly.
✨ With its prime location, luxury amenities, and easy beach access, Chasing Sunsets is the perfect choice for your next Anna Maria Island getaway.
Book now at BeachRetreatsFL

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  • Feature Features
  • Map Map
  • School District Availability
  • Review Review

Feature Features

  • PETS

    Service Animals Only (pets Not Allowed)
  • BEACH

    Near The Beach
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Not Reported (host Has Not Indicated Whether There Is A Carbon Monoxide Detector On The Property; Consider Bringing A Portable Detector) Smoke Detector Not Reported (host Has Not Indicated Whether There Is A Smoke Detector On The Property)
  • BEDROOM

    4 Bedrooms Bed Sheets Provided
  • GENERAL

    Unit Size: 2200 Sq Ft (204 Sq M)
  • KITCHEN

    Coffee/tea Maker Cookware/dishes/utensils Dishwasher Microwave Oven Refrigerator Spices Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Near Laundromat Washing Machine And Dryer
  • PARKING

    Onsite Parking Onsite Parking Options Include A Garage
  • INTERNET

    Free WiFi
  • OUTDOORS

    Balcony Barbecue Grill Garden
  • POOL/SPA

    Heated Pool Hot Tub Private Pool
  • BATHROOMS

    3 Bathrooms Hair Dryer Shower Towels Provided
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Basketball Nearby Birdwatching Nearby Casino Nearby Fitness Facilities Nearby Golf Nearby Hiking Nearby Parasailing Nearby Sailing Nearby Snorkeling Nearby Tennis On Site Water Park Windsurfing Nearby
  • ENTERTAINMENT

    Games TV With Cable/satellite Service
  • LIVING SPACES

    Dining Room Living Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Highchair Travel Crib
  • LOCATION HIGHLIGHTS

    In A Village In The City Center Near A Health Or Beauty Spa Near A Hospital Near A Zoo Near Outlet Shopping Near The Bay Near The Sea
  • SERVICES AND CONVENIENCES

    Iron/ironing Board Phone
  • SUITABILITY/ACCESSIBILITY

    Elevator If You Have Requests For Specific Accessibility Needs, Please Contact The Property Using The Information On The Reservation Confirmation Received After Booking. Smoke-free Property Wheelchair Accessible

CheckIn Check-in : 04:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 8

Map Map

School District Availability

Review Review

  • Paris W.

    Submitted Oct 16, 2025

    Stayed Sep 25, 2025

    Host was super helpful. Quick communications and to resolve issues.

  • Christie O.

    Submitted Jul 30, 2025

    Stayed Jul 12, 2025

    The house was beautiful and had everything we needed for a great vacation.

  • Stacey P.

    Submitted May 30, 2025

    Stayed May 2, 2025

    The property is go

  • BRANDON D.

    Submitted Jul 31, 2024

    Stayed Jul 20, 2024

    Definitely the best property we have booked. Well worth it!

  • Michele H.

    Submitted May 26, 2024

    Stayed May 19, 2024

    We had an amazing week at Chasing Sunsets. The house was clean, very well stocked and had great proximity to the beach, making it so easy. We arrived an hour before check in after a rocky flight. We so appreciated being let into this beautiful home early! We enjoyed the pool, the grill and some much needed time to reset, unwind and enjoy our family. We will definitely be back. Thank you for making our stay so fabulous!

  • Doug S.

    Submitted Apr 8, 2024

    Stayed Mar 19, 2024

    This was my first stay at a property owned by a large corporate entity and it did not meet my expectations. The condition of the property was excellent, cleanliness good, the listing accurate and the location is great, but it was devoid of the personal touches I've come to expect over the last 15 years of renting on the island. We rented two places this trip, this one and another very modest one for the grandparents to hideout in. The other place was very basic without even a dishwasher, but it had all the extras I've come to expect - coffee, coffee filters, extra garbage bags, dish cleaning fluids, basic condiments, toilet paper for the week, sharp knives and clothes washing fluids. They even included two bottles of wine (I've never seen that before). In fairness to the host I didn't contact them about the deficiencies to give them a chance to correct things. I'm on vacation and don't expect to act in a quality control capacity. Here were the problems: - dishwasher filter and arms filthy and clogged (I have the same model at home so I cleaned it myself) Put that on your cleaners checklist - dishwasher did not dry dishes (I suspect the heating element is burned out) Your cleaner should have noted this - knives are very dull and thus dangerous (I brought a knife sharpener from the other place, but it could only do so much) - no coffee filters (I bring coffee, but don't know which filters to get) - General lack of consumables Limited space for comments (I'm verbose)

  • Billy S.

    Submitted Mar 5, 2024

    Stayed Feb 28, 2024

    Perfect location beach was amazing. Pool was absolutely the best and the house was extremely clean. We will definitely want to stay here again beautiful house.

  • katie M.

    Submitted Feb 1, 2024

    Stayed Jan 13, 2024

    This was our favorite home that we rented. The layout and location are perfect. We loved the pool and spa. An issue we found on move in was quickly addressed by the property manager. We did feel the house could use a deep clean- baseboards, under bed dusting, etc. My husband had to take apart and clean the filter on the dishwasher because of an awful smell but that resolved the situation. Also, we think that a mention in the listing about the pool heater not working when the outside temperature falls below 69 is important because we rented this particular house specifically so we would have a hot tub if it was cold. This kind of caused panic during check in. I will say that despite that, even though we had a cold week during our stay (50s and 60s) we were able to keep the hot tub warm and use it every day. Whew! We are hoping to be able to rent this house again. It was great for our family!

  • Jose S.

    Submitted Aug 12, 2023

    Stayed Aug 7, 2023

    This was the perfect house and perfect location for our family vacation. The pool gets good shade throughout the day and the outdoor living area is covered for when you need a break from the sun. The inside of the house was immaculate and comfortable for our family of 7. My kids have already requested we come back to the same house next year.

  • Jessica R.

    Submitted Aug 7, 2023

    Stayed Jul 30, 2023

    great location on a quiet street just steps to the beach, updated home, beautiful outdoor pool and covered patio with tv, great proximity restaurants, Pine Ave, and local coffee shops

Your dates are Available!

Total

Includes taxes and fees
$878+
View details