Entire home

Chasing Sunsets managed by Beach Retreats FL Anna Maria Island

Photo gallery for Chasing Sunsets managed by Beach Retreats FL Anna Maria Island

A beachfront property with a pool, palm trees, and a large house with a blue facade.
A spacious living room with a large sectional sofa, a gray armchair, and a coffee table. There are large windows providing natural light and a view of the outdoors.
A modern kitchen with white cabinets, a large island with bar stools, and pendant lighting.
A covered outdoor seating area with wooden furniture and a ceiling fan.
A spacious kitchen with white cabinetry, a dining area with a wooden table and chairs, and a large window providing natural light.

Reviews

9.6 out of 10
Exceptional
Overlooking the ocean, this 4-bedroom vacation home accommodates 8 guests and features 3 bathrooms. It includes 1 hot tub and offers options for sailing and birdwatching nearby. Enjoy the patio and explore attractions like Bradenton Beach and Palmetto Avenue Beach.

Highlights

  • Family fun awaits

    Top-rated for families.

  • Private garden

    A rare find — relax in the peaceful, private garden space.

  • Discover nearby landmarks

    Walk to Bradenton Beach
4 bedrooms3 bathroomsSleeps 8

Popular amenities

  • Waterpark access
  • Private pool
  • Patio
  • Outdoor barbecue
  • Air-conditioning
  • Washing machine

Explore the area

View map
Bradenton Beach, FL
  • Place, Bradenton Beach
    ‪3 min walk‬
  • Place, Palmetto Avenue Beach
    ‪18 min walk‬
  • Place, Anna Maria Island Museum and Historical Park
    ‪3 min drive‬
  • Airport, Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
    ‪38 min drive‬

Where you'll sleep

4 bedrooms (sleeps 8)

Built in Bunks

1 Single Bunk Bed

King Bed

1 King Bed

King bed with ensuite bathroom and balcony with peeks of the

1 King Bed

Queen Bed

1 Queen Bed

3 bathrooms

Bathroom 2

Toilet · Shower only

Bathroom 3

Toilet · Shower only

Full Bath

Toilet · Shower only

Spaces

Deck or patio
Porch or lanai
Kitchen
Balcony
Separate dining area
Garden
Dining area

About this property

Chasing Sunsets managed by Beach Retreats FL Anna Maria Island

🌅 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 a perfect 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
20% deposit due at booking; balance due 60 days prior to arrival
Cancel 60+ days before arrival → Lose 20% deposit
Cancel within 60 days → No refund
Extended stays & bookings $25,000+ → Full payment 90 days prior, non-refundable
You may cancel your reservation within 24 hours of booking for a full refund, no questions asked. This grace period does not apply to reservations made within 60 days of arrival — these bookings are non-refundable from the time of booking.
Third party travel insurance cost is due at time of purchase
We highly recommend cancelation insurance
Guests must be 25+ to book (or accompanied by parent/guardian)
🎧Quiet hours: 10 PM – 7 AM; please respect neighbors
We prefer Saturday to Saturday rentals. If you're looking to stay other days, please give us a call.
​​​​​​​🚗 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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House Rules

Check in after 4:00 PM

Minimum age to rent: 25

Check out before 10:00 AM

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Children

Children allowed: ages 0–17

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Events

No events allowed

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Pets

No pets allowed, service animals permitted

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Smoking

Smoking is not permitted

Important information

You need to know

Property # 3304296vb
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 not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property

About the area

Holmes Beach

Located in Holmes Beach, this holiday home is in the city centre and near the beach. The area's natural beauty can be seen at Bradenton Beach and Bean Point Beach. Travelling with kids? Consider Fish Hole Adventure Golf, or check out an event or a game at LECOM Park. Jet skiing and kayaking offer great chances to get out on the surrounding water, or you can seek out an adventure with mountain biking and hiking nearby.
View more Holiday homes in Holmes BeachOpens in a new window
Map
Bradenton Beach, FL

What's nearby

  • Bradenton Beach - 3 min walk - 0.3 km
  • Palmetto Avenue Beach - 18 min walk - 1.6 km
  • Island Players - 3 min drive - 2.1 km
  • Anna Maria Island Museum and Historical Park - 3 min drive - 2.4 km
  • Holmes Beach Beaches - 8 min drive - 3.1 km

Getting around

  • Sarasota, FL (SRQ-Sarasota-Bradenton Intl.) - 39 min drive

Restaurants

  • ‪The Sandbar Restaurant - ‬20 min walk
  • ‪Anna Maria Island Beach Cafe - ‬6 min drive
  • ‪The Ugly Grouper - ‬3 min drive
  • ‪Ginny's & Jane E's - ‬17 min walk
  • ‪The Waterfront Restaurant - ‬4 min drive

Frequently asked questions

Is Chasing Sunsets managed by Beach Retreats FL Anna Maria Island pet-friendly?

No, only service animals are welcome at the property.

How much is parking at Chasing Sunsets managed by Beach Retreats FL Anna Maria Island?

On-site parking is available at the property.

What time is check-in at Chasing Sunsets managed by Beach Retreats FL Anna Maria Island?

Check-in begins at 4:00 PM.

What time is check-out at Chasing Sunsets managed by Beach Retreats FL Anna Maria Island?

Checkout is at 10:00 AM.

Where is Chasing Sunsets managed by Beach Retreats FL Anna Maria Island located?

This family-friendly Holmes Beach holiday home is located by the sea, within 1 mi (2 km) of Bradenton Beach, Palmetto Avenue Beach and Island Players. Bean Point Beach and Bay Boulevard Beach are also within 2 miles (3 km).

Reviews

9.6

Exceptional

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. 13 out of 18 reviews
Rating 8 - Good. 5 out of 18 reviews
Rating 6 - Okay. 0 out of 18 reviews
Rating 4 - Poor. 0 out of 18 reviews
Rating 2 - Terrible. 0 out of 18 reviews

9.4/10

Cleanliness

10/10

Check-in

9.2/10

Communication

10/10

Location

9.4/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great property! Nicely decorated! It was about a 2 minute walk to the beach! Pretty sunsets with white sand beach. Great family setup , plenty of room for kids. Private pool and Lanai.
Stayed 4 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great property backyard nicer than pictures. Ice maker freezer broken only negative . Great place for two families!
Stayed 7 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location. A perfect place to relax for a week.
Stayed 7 nights in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful house and location

The house was beautiful and had everything we needed for a great vacation.
Stayed 7 nights in Jul 2025
Response from VrboOwner on 13 August 2025
Hi Christie, Thank you for taking the time to review our Beach Retreat, Chasing Sunsets. We are so happy you found the home beautiful and everything needed for a great vacation. We do hope to host you the next time your travels bring you to Anna Maria Island!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house was wonderful. It was well-organized. They were easy to communicate with. I would suggest you make sure to bring along trash bags as they only provide the first set and then you are on your own after. Other than that, we were well-stocked :)
Stayed 3 nights in Apr 2026
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location
Host was super helpful. Quick communications and to resolve issues.
Stayed 11 nights in Sep 2025
Response from VrboOwner on 14 November 2025
Hi Paris, Thank you for taking the time to review our Beach Retreat, Chasing Sunsets. We are thrilled we were quick to resolve issues and respond to communication. We hope to host you again the next time your travels bring you to Anna Maria Island.
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location, clean, updated

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
Stayed 7 nights in Jul 2023
Response from VrboOwner on 13 September 2023
Hi Jessica, Thank you for taking the time to review our Beach Retreat, Chasing Sunsets. We are thrilled to hear you enjoyed your stay. We love the location of this home and the proximity to the beach and Pine Ave. We hope to host you again the next time your travels bring you to Anna Maria Island.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Bill stone

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.
Stayed 6 nights in Feb 2024
Response from VrboOwner on 22 March 2024
Hi Billy, Thank you for taking the time to review our Beach Retreat, Chasing Sunsets. We are thrilled to hear you enjoyed your stay! We strive to go above and beyond and I'm so happy we met that goal. We look forward to hosting you the next time your travels bring you to Anna Maria Island.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing

Definitely the best property we have booked. Well worth it!
Stayed 8 nights in Jul 2024
Response from VrboOwner on 21 August 2024
Hi Brandon, Thank you for taking the time to review our Beach Retreat Chasing Sunsets. We are thrilled you feel this is the best property! We look forward to hosting you the next time your travels bring you to Anna Maria Island.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, location
The property is go
Stayed 7 nights in May 2025
Response from VrboOwner on 17 June 2025
HI Stacey, Thank you for taking the time to review our Beach Retreat, Chasing Sunsets. We hope you enjoyed your stay! We hope to host you again the next time your travels bring you to Anna Maria Island.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family Vacation

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.
Stayed 5 nights in Aug 2023
Response from VrboOwner on 13 September 2023
Hi Jose, Thank you for taking the time to review our Beach Retreat, Chasing Sunsets. We are thrilled to hear you enjoyed your stay! We look forward to hosting you all next year!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

A perfect week!

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!
Stayed 7 nights in May 2024
Response from VrboOwner on 11 July 2024
Hi Michele, Thank you for taking the time to review our Beach Retreat, Chasing Sunsets. We are thrilled to hear you enjoyed your stay and we were able to accommodate an early check in. It's not a privilege we are always able to provide, but we try to when we can. This backyard area is a great place to relax and eat all those grilled meals. We do hope to host you the next time your travels bring you to Anna Maria Island!
Verified review

8/10 Good

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

Lovely home

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!
Stayed 7 nights in Jan 2024
Response from VrboOwner on 1 March 2024
Hi Katie, Thank you for taking the time to review our Beach Retreat, Chasing Sunsets. We are thrilled to hear you enjoyed your stay! We strive to go above and beyond. We look forward to hosting you the next time your travels bring you to Anna Maria Island, and we hope with warmer weather. We are discussing the listing information about the pool.
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy

Good but not Great

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)
Stayed 8 nights in Mar 2024
Verified review

10/10 Excellent

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

Perfektes Haus in Strandnähe

Das Haus hat uns sehr gut gefallen. Die Beschreibung auf der Homepage entspricht genau den Tatsachen. Einziger Kritikpunkt: Die Spülmaschine müsste ersetzt werden. Der Backofen und der Grill waren nicht sauber.
Stayed 7 nights in Apr 2025
Response from VrboOwner on 9 May 2025
Hallo Christina, Vielen Dank, dass Sie sich die Zeit genommen haben, unser Strandresort Chasing Sunsets zu bewerten. Wir freuen uns, dass Ihnen das Haus gefallen hat! Wir werden uns wegen der Spülmaschine mit den Eigentümern in Verbindung setzen. Es tut uns sehr leid, dass Backofen und Grill nicht gereinigt wurden. Hätten wir Bescheid bekommen, hätten wir die Reinigungskräfte zurückschicken können. Wir hoffen, Sie bei Ihrer nächsten Reise nach Anna Maria Island wieder bei uns begrüßen zu dürfen.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, location, listing accuracy
Disliked: Communication
Stayed 7 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 4 nights in May 2025
Response from VrboOwner on 18 July 2025
Hi Summer, Thank you for taking the time to review our Beach Retreats, Chasing Sunsets. We are thrilled for the 5 star review! We hope to host you again the next time your travels bring you to Anna Maria Island!
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 7 nights in Apr 2025
Response from VrboOwner on 17 June 2025
Hi Becky, Thank you for taking the time to review our Beach Retreat, Chasing Sunsets. We hope you enjoyed your stay! We hope to host you the next time your travels bring you to Anna Maria Island!

About the host

Hosted by Beach Retreats

Host profile image

Beach Retreats Vacation Rentals

As a small boutique rental agency, we pride ourselves on selecting only a handful of the newest, most pristine vacation rentals. We have chosen homes to suit all group sizes and specifications without compromising the highest standards we hold ourselves to. Being this discerning has earned us the trust of many vacationers who have come back year after year.

We are also one of the few agencies with a focus on homes from Anna Maria Island to Siesta Key. We know that while many people are happy to return to the same vacation spot year after year, others like to try out new places. We hope our personalized service and spectacular homes will allow you to truly experience the islands as they were meant to be!

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They consistently provide great experiences for their guests

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