Entire home

Chasing Sunsets managed by Beach Retreats FL Anna Maria Island

Roof top deck, perfect for catching all the sunsets

Main level bathroom with large walk-in shower with double vanitys

Overview
Amenities
Policies
Location
Host

Exceptional

4 bedrooms3 bathroomsSleeps 82200 sq ft

Popular amenities

Parking available
Dryer
Washer
Hot tub
Air conditioning
Pool

Explore the area

Bradenton Beach, FL

Bradenton Beach
‪3 min walk‬
Bean Point Beach
‪5 min drive‬
Anna Maria Beach
‪6 min drive‬
Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
‪36 min drive‬

Rooms & beds

4 bedrooms (sleeps 8)

Built in Bunks

1 Single Bunk Bed

Common Space

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.
🌟 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
$500 deposit due at time of booking; balance due 30 days prior to arrival
Cancel 30+ days before arrival → Full refund
Cancel within 30 days → No refund
Extended stays (2+ weeks) or $20,000+ bookings → Full payment due 45 days prior
All changes/cancellations must be in writing
⚠️ 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

Property manager

Beach Retreats

Premier Host

Languages

English

Add dates for prices

Amenities

Pool

Hot tub

Kitchen

Washing machine

Dryer

Free WiFi

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Pool
Hot tub
Kitchen
Washer

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

No pets allowed, service animals permitted

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

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 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.

Bradenton Beach, FL

What's nearby

Bradenton Beach - 3 min walk - 0.3 km
Anna Maria City Pier - 5 min drive - 2.5 km
Manatee Public Beach - 5 min drive - 2.8 km
Bean Point Beach - 5 min drive - 3.1 km
Anna Maria Beach - 6 min drive - 3.8 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
‪Skinny's Place - ‬6 min drive
‪Hurricane Hanks - ‬4 min drive
‪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.

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).

9.4

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.

Learn more

9.0/10

Cleanliness

10/10

Check-in

9.4/10

Communication

10/10

Location

9.4/10

Listing accuracy

10/10 Excellent

Christie O.

30 Jul, 2025

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

10/10 Excellent

Stacey P.

30 May, 2025

Liked: Cleanliness, check-in, location

The property is go

Stayed 7 nights in May 2025

10/10 Excellent

BRANDON D.

31 Jul, 2024

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

10/10 Excellent

Billy S.

5 Mar, 2024

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

8/10 Good

Jessica R.

7 Aug, 2023

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

10/10 Excellent

Jose S.

12 Aug, 2023

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

10/10 Excellent

Michele H.

26 May, 2024

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

8/10 Good

katie M.

1 Feb, 2024

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

10/10 Excellent

Summer B.

17 Jun, 2025

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

Stayed 4 nights in May 2025

8/10 Good

Becky L.

26 May, 2025

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

Stayed 7 nights in Apr 2025

10/10 Excellent

Christina Maria R.

15 Apr, 2025

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

8/10 Good

Doug S.

8 Apr, 2024

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

About the host

Hosted by Beach Retreats

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!