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Chasing Sunsets managed by Beach Retreats FL Anna Maria Island

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A covered outdoor seating area with white furniture and a view of the surrounding buildings and palm trees.
A spacious kitchen with white cabinetry, a dining area with a wooden table and chairs, and a large window providing natural light.
A swimming pool with a tiled deck, surrounded by palm trees and a white building with arched doorways.
Property grounds
Beach nearby

Reviews

9.4 out of 10
Exceptional

Entire home

4 bedrooms3 bathroomsSleeps 8204 sq m

Popular amenities

  • Ocean view
  • Pool
  • Spa pool
  • Kitchen
  • Washing machine
  • Dryer

Explore the area

View map
Bradenton Beach, FL
  • Place, Bradenton Beach
    ‪3 min walk‬
  • Place, Palmetto Avenue Beach
    ‪18 min walk‬
  • Place, Island Gallery West
    ‪3 min drive‬
  • Airport, Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
    ‪38 min drive‬

Room options

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About the area

Holmes Beach

A family-friendly stay in the heart of Holmes Beach awaits you at this holiday home. You'll be steps from Bradenton Beach and 2.5 km (1.6 mi) from Bean Point Beach. Highlights at this holiday home include a kitchen, a private pool and a washing machine. .Home features free WiFi, 3 bathrooms and a balcony. In-room dining is easy with a kitchen that comes equipped with a fridge, a microwave and a stovetop. A living room, a dining area and a TV are also available. .Enjoy the water park and Hot tub. Additionally, you'll find laundry facilities, a garden and barbecues. .Attractions within a 10-minute drive of this Holmes Beach holiday home include Anna Maria Beach and Cortez Beach.
View more Holiday homes in Holmes BeachOpens in a new window

What's nearby

  • Bradenton Beach - 3 min walk - 0.3 km
  • Palmetto Avenue Beach - 18 min walk - 1.6 km
  • Island Gallery West - 3 min drive - 1.7 km
  • Island Players - 3 min drive - 2.1 km
  • Anna Maria Island Museum and Historical Park - 3 min drive - 2.4 km

Getting around

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

Restaurants

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

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

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
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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Villa (2 Bedrooms) | Interior
Near Beaches: Waterfront Gem in Anna Maria Island!
Holmes Beach
  • Kitchen
  • Washing machine
  • Dryer
  • Parking included
Near Beaches: Waterfront Gem in Anna Maria Island!

Property amenities

Beach

  • Beach nearby

Pool/Spa

  • Heated pool
  • Hot tub
  • Private pool

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Onsite parking options include a garage

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Hob
  • Microwave
  • Oven
  • Refrigerator
  • Spices
  • Toaster

Dining

  • Dining table

Bedrooms

  • 4 bedrooms
  • Bedsheets provided

Bathroom

  • 3 bathrooms
  • Hair dryer
  • Shower
  • Towels provided

Living spaces

  • Dining table
  • Living room
  • Separate dining area

Entertainment

  • Games
  • TV with cable/satellite channels

Outdoor areas

  • Balcony
  • Barbecue grill
  • Garden

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • Service animals only (pets not allowed)

Suitability/Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • In-room accessibility
  • Lift
  • Smoke-free property

Services and conveniences

  • Iron/ironing board
  • Phone

Location highlights

  • In a village
  • In the city centre
  • Near a health/beauty spa
  • Near a hospital
  • Near a zoo
  • Near an outlet shopping centre
  • Near the bay
  • Near the marina
  • Near the sea

Things to do

  • Heated pool
  • Tennis
  • Water park
  • Basketball nearby
  • Birdwatching nearby
  • Casino nearby
  • Ecotours nearby
  • Fishing nearby
  • Golfing nearby
  • Hiking/biking trails nearby
  • Horseback riding nearby
  • Jet skiing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Mountain biking nearby
  • Parasailing nearby
  • Sailing nearby
  • Scuba diving nearby
  • Snorkelling nearby
  • Swimming nearby
  • Theme park nearby
  • Water skiing nearby
  • Water tubing nearby
  • Wildlife walks nearby
  • Windsurfing nearby
  • Winery tours nearby

Safety features

  • 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)

General

  • Garden
  • Unit size: 2,200 square feet

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in and check-out are available
Minimum check-in age - 25

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Pets

  • No pets allowed, but service animals are welcome

Children and extra beds

  • Children are welcome.

Events

No events 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 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
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business or profession. On-site parties or group events are strictly prohibited.

Property is also known as

598066

Frequently asked questions

Are there any beaches close to Chasing Sunsets managed by Beach Retreats FL Anna Maria Island?

Yep, Chasing Sunsets managed by Beach Retreats FL Anna Maria Island is a short 2-minute walk from Bradenton Beach. Fun beach activities include jet skiing, snorkelling and scuba diving. You can also find motor boats.

Does Chasing Sunsets managed by Beach Retreats FL Anna Maria Island have a pool?

Chasing Sunsets managed by Beach Retreats FL Anna Maria Island has a heated pool.

Does Chasing Sunsets managed by Beach Retreats FL Anna Maria Island have a waterslide?

No, but it has a waterpark and lazy river.

What luxury perks are available at Chasing Sunsets managed by Beach Retreats FL Anna Maria Island?

This property features a heated pool, as well as a private pool and a living room.

What makes Chasing Sunsets managed by Beach Retreats FL Anna Maria Island a romantic place to stay?

1 hot tub, private pools, and private balconies all help set the scene for a sizzling getaway at Chasing Sunsets managed by Beach Retreats FL Anna Maria Island.

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

You bet! With amenities such as a water park and laundry facilities, as well as highchairs and travel cots, it's no surprise that Chasing Sunsets managed by Beach Retreats FL Anna Maria Island is a winner with our family travellers.

Is there a private hot tub at Chasing Sunsets managed by Beach Retreats FL Anna Maria Island?

Yep, there is a hot tub.

Is there a free airport shuttle available at Chasing Sunsets managed by Beach Retreats FL Anna Maria Island?

No, Chasing Sunsets managed by Beach Retreats FL Anna Maria Island does not offer an airport shuttle service.

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

Check-in begins at 4:00 PM. Check-out time is 10:00 AM.

Are pets allowed at Chasing Sunsets managed by Beach Retreats FL Anna Maria Island?

No, only service animals are allowed.

Chasing Sunsets managed by Beach Retreats FL Anna Maria Island Reviews

Reviews

9.4

Exceptional

Rating 10 - Excellent. 11 out of 16 reviews
Rating 8 - Good. 5 out of 16 reviews
Rating 6 - Okay. 0 out of 16 reviews
Rating 4 - Poor. 0 out of 16 reviews
Rating 2 - Terrible. 0 out of 16 reviews

9.2/10

Cleanliness

Reviews

Verified

10/10 Excellent

Lora J.

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

10/10 Excellent

Christie O.

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
Verified

8/10 Good

Paris W.

Liked: Cleanliness, check-in, communication, location
Host was super helpful. Quick communications and to resolve issues.
Stayed 11 nights in Sep 2025
Verified

8/10 Good

Jessica R.

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
Verified

10/10 Excellent

Billy S.

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
Verified

10/10 Excellent

Stacey P.

Liked: Cleanliness, check-in, location
The property is go
Stayed 7 nights in May 2025
Verified

10/10 Excellent

BRANDON D.

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
Verified

10/10 Excellent

Jose S.

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
Verified

10/10 Excellent

Michele H.

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
Verified

8/10 Good

katie M.

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
Verified

8/10 Good

Doug S.

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

10/10 Excellent

Christina Maria R.

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
Verified

10/10 Excellent

Summer B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 4 nights in May 2025
Verified

8/10 Good

Becky L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 7 nights in Apr 2025

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