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Sunnyside of the Beach: Updated, 5-bedroom home, pool, close to beach!

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A heated pool - Sunnyside of the Beach: Updated, 5-bedroom home, pool, close to beach! (Holmes Beach)
Fridge, microwave, oven, stovetop - Sunnyside of the Beach: Updated, 5-bedroom home, pool, close to beach! (Holmes Beach)
Interior - Sunnyside of the Beach: Updated, 5-bedroom home, pool, close to beach! (Holmes Beach)
Smart TV, books - Sunnyside of the Beach: Updated, 5-bedroom home, pool, close to beach! (Holmes Beach)
Smart TV, books - Sunnyside of the Beach: Updated, 5-bedroom home, pool, close to beach! (Holmes Beach)
Nestled in the heart of Holmes Beach, Sunny Side of the Beach offers an elegant island retreat with a state-of-the-art kitchen and beautifully decorated living areas. Enjoy maximum privacy in one of five cozy bedrooms or unwind by the heated pool and miniature waterfall.

Reviews

9.0 out of 10
Wonderful

Entire home

5 bedrooms3 bathroomsSleeps 10

Popular amenities

  • Pool
  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning

Add dates for prices

About this property

Entire place

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

Sunnyside of the Beach: Updated, 5-bedroom home, pool, close to beach!

If you are looking to enjoy Anna Maria Island in a beautiful home, look no further than "Sunny Side of the Beach" on 66th Street. This five bedroom, 3 bathroom island paradise, nestled into the city of Holmes Beach, is equipped with a beautiful, state of the art kitchen fully supplied with all the cookware, appliances and other kitchen supplies to allow for the full expression of your inner gourmet chef. The home is beautifully decorated with understated beach house elegance throughout. The five bedrooms-each of them comfortable, cozy and bright-are arranged for maximum privacy, with flat screen TVs and cable access.

Conveniences abound here: the washer and dryer are top of the line, and Wi Fi gives you complete internet connectivity throughout the house. The spacious living and dining areas are perfect for getting together after a day at the beach. Or, lounge together by the heated pool and miniature waterfall while grilling on the gas grill on the patio, secluded by beautiful native landscaping and adorned by the finest in patio furniture.

One of the world's most beautiful beaches is just a few steps-yes, literally just a few short steps, less than a block away-from the front door. The sunsets over the Gulf horizon are breathtaking. If you're in the mood to go out, you're just a short bike ride away from all of the best shopping, dining and sight-seeing that Anna Maria Island has to offer. Indeed, cozy and comfortable meet luxury and convenience at "Sunny Side of the Beach" on 66th Street. You and your family and friends will experience the vacation of a lifetime here.

Bedroom 1: King with TV on Floor 1
Bedroom 2: King Master with TV on Floor 2
Bedroom 3: King with TV on Floor 3
Bedroom 4: King with TV on Floor 3
Bedroom 5: 2 Twin-over-Twin Bunk Beds on Floor 1
*The bed configuration was recently updated in the fall of 2022 and may not be reflected in the photos.

*Please note: 4 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles.

***OVERCROWDING CONSEQUENCES***
Maximum occupancy of rental homes on Anna Maria Island are set by the Cities and are strictly enforced. An occupant is any person staying overnight, regardless of the number of nights. Due to recent issues of overcrowding in the area, if maximum occupancy is exceeded during your stay, a $1000 (one thousand dollar) overcrowding fee will be charged to the payment method on file and your party will be immediately evicted. We appreciate your understanding and cooperation to keep Anna Maria Island enjoyable for everyone.

"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."
*Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

VRC16-000209

Property amenities

Pool/Spa

  • Heated pool
  • Private pool

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Car recommended
  • Onsite parking options include a garage

Kitchen

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

Bedrooms

  • 5 bedrooms
  • Bedsheets provided

Bathroom

  • 3 bathrooms
  • Hair dryer
  • Shower/bathtub combination
  • Towels provided

Living spaces

  • Living room

Entertainment

  • Books
  • Games
  • Smart TV with cable/satellite channels

Outdoor areas

  • Gas grill
  • Outdoor furniture

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board
  • Phone

Things to do

  • Golf
  • Heated pool
  • Kayak
  • Ecotours nearby
  • Fishing nearby
  • Motor boating nearby
  • Parasailing nearby
  • Sailing nearby
  • Scuba diving nearby
  • Surfing/bodyboarding nearby
  • Swimming nearby
  • Water tubing nearby
  • Wildlife walks nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher
  • Deadbolt lock

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Exterior
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  • Parking included
8.6 out of 10, Excellent, 699 reviews
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Policies

Check-in

Check-in time starts at 3:00 PM

Contactless check-in and check-out are available

Minimum check-in age - 21

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

Pets not allowed

Children and extra beds

Children are welcome

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
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 indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadlock
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
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with UK consumer law, property booking services are not subject to the right of withdrawal.

We should mention

A car is recommended for transport to and from this property

About the area

Located in Holmes Beach, this holiday home is near a water park. The area's natural beauty can be seen at Bradenton Beach and Bean Point Beach. Looking to enjoy an event or a game while in town? See what's happening at LECOM Park or IMG Bollettieri Tennis Academy. Scuba diving, water tubing and parasailing offer great chances to get out on the surrounding water, or you can seek out an adventure with ecotours nearby. Visit our Holmes Beach travel guide
View more Holiday homes in Holmes Beach
Map
Holmes Beach, FL

What's nearby

  • Sarasota, florida, bradenton beach, Shutterstock ID 1052846027, Purchase Order: Wave 0 First Batch, Order Number: , Client/Licensee: Hotels.com / BEX, Other: Mixed Budget
    Bradenton Beach
    2 min walk - 0.1 miles
  • Palmetto Avenue Beach
    Palmetto Avenue Beach
    20 min walk - 1.1 miles
  • Sarasota_ManateePublicBeach_6296224-6
    Manatee Public Beach
    3 min drive - 1.3 miles
  • Island Gallery West
    12 min walk - 0.7 miles
  • Holmes Beach Beaches
    7 min drive - 1.5 miles

Getting around

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

Restaurants

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

Frequently asked questions

Does Sunnyside of the Beach: Updated, 5-bedroom home, pool, close to beach! have a pool?

Yes, this property has a pool. Pool types include heated pools.

Is Sunnyside of the Beach: Updated, 5-bedroom home, pool, close to beach! pet-friendly?

No, pets are not allowed at this property.

How much is parking at Sunnyside of the Beach: Updated, 5-bedroom home, pool, close to beach!?

On-site parking is available at the property.

What time is check-in at Sunnyside of the Beach: Updated, 5-bedroom home, pool, close to beach!?

Check-in begins at 3:00 PM.

What time is check-out at Sunnyside of the Beach: Updated, 5-bedroom home, pool, close to beach!?

Checkout is at 10:00 AM.

Where is Sunnyside of the Beach: Updated, 5-bedroom home, pool, close to beach! located?

Situated in Holmes Beach, this holiday home is within a 15-minute walk of Bradenton Beach and Island Gallery West. Palmetto Avenue Beach and Holmes Beach Beaches are also within 1 mile (2 km).

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Sunnyside of the Beach: Updated, 5-bedroom home, pool, close to beach! Reviews

Reviews

Wonderful

All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
More informationOpens in a new window
Rating 10 - Excellent. 28 out of 46 reviews
Rating 8 - Good. 12 out of 46 reviews
Rating 6 - Okay. 4 out of 46 reviews
Rating 4 - Poor. 2 out of 46 reviews
Rating 2 - Terrible. 0 out of 46 reviews

8.8

Cleanliness

9.8

Location

Reviews

Verified

8/10 Good

Mike S.

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

Anniversary Celebration!

This house worked perfectly for our three families with a total of 10 people. The younger grand kids loved the bunk room and the teenager loved sleeping upstairs. The close proximity to the beach and having the pool made it fun for everyone. We would definitely stay here again!
Stayed 5 nights in Jul 2024
Verified

8/10 Good

Mary M.

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

Great location, a few details meed attention.

We loved our stay, and the easy proximity to the beach! The good; a very comfortable home base for our group. The not so good; some of the appliances in the kitchen were subpar. The dishwasher was on its last leg and broke while we were there. Bummed to have to wash all the dishes by hand for four days. However, they did replace it at the end of our stay, so that isn’t a problem anymore. The refrigerator has no door storage compartments, and the lower bin in the fridge is inoperable. Also, the ice maker does not work. Hopefully they will replace that soon. The bathrooms all need more towel bars, and the master bathroom needs to replace the missing toilet paper holder. Having said that, it was a good place for our family to use and visit grandparents who live in the area.
Stayed 14 nights in Nov 2023
Verified

10/10 Excellent

Edith A.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Had an amazing stay ! Property is a VERY close walk to the beach. An amazing house, pictures make it look smaller than it is !! Loved it, will be going back!
Stayed 3 nights in Jul 2025
Verified

8/10 Good

DONNA T.

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

Great location!

Great location
Stayed 7 nights in Oct 2021
Archival

10/10 Excellent

Cassie B.

Great Stay!

Spacious, clean, beautifully decorated, private pool in back, and walking distance to the beach- what more could you ask for?! I will definitely visit again!
Verified

10/10 Excellent

Diane M.

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

Great location comfortable home

The property was in a perfect location so close to the beach and in walking distance of a variety of restaurants. Inside the home was lovely, everything looked newly updated. The pool was very nice and warm.
Stayed 4 nights in Jan 2023
Verified

10/10 Excellent

Alicia C.

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

Very cute house!!

Cute place! Shirt easy walk up to the beach! Centrally located foe bike or golf cart rides to restaurants and shops.
Stayed 7 nights in Dec 2020
Verified

10/10 Excellent

matthew T.

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

Family enjoyed!

We had a great time! The pool was a hit with the kids!! Property Manager was great helping with a few questions during our stay. Enjoyed the quick walk to the beach to view the sunset.
Stayed 7 nights in Jan 2023
Verified

8/10 Good

Carrie B.

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

Great location!!

This house was in an amazing location! Quick access to the beach! We had a blast having 9 people all together in the house. We struggled cooking meals as the pots and pans were in terrible condition. We had a few minor issues and the rental property came out right away to address them. Overall we had a great time and made lots of memories!
Stayed 6 nights in May 2025
Verified

10/10 Excellent

Linda R.

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

Beautiful vacation home!

Wow! This home was so much lovelier than the pictures! This was a girls trip and the 7 of us fit so comfortably in this home. The management responded immediately to a few minor issues, check in was easy and location was perfect.
Stayed 7 nights in Jun 2023
Verified

6/10 Okay

Colleen G.

Liked: Cleanliness, check-in, communication, location

Great Location

We loved that we were within walking distance of the beach. The house was clean and the beds were comfortable. The water pressure in the shower was great. We were surprised that there were only 2 new rolls of toilet paper provided (there were partial rolls in the 3 bathrooms). I would encourage renters to bring additional dish soap, dishwasher soap, laundry soap, toilet paper and paper towels. Overall we had a good time. The property management company was quick to respond to our concerns (the TV in the living room needed to be re-connected to the network and the garbage disposal needed to be replaced).
Stayed 4 nights in Jul 2025
Verified

10/10 Excellent

Edward S.

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

An Excellent Property

Excellent property that has recently been completely refurbished. That of course came with some minor issues all of which were handled promptly and completely by the property manager. The walk to the beach was 3 minutes. We also could walk to multiple restaurants and shops. Dave our neighbor was very nice and helpful.
Stayed 7 nights in Dec 2022
Verified

10/10 Excellent

Sheryl D.

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

girls week at the beach

Nice property with great location overall. Beach is just 1/2 block away. Beach chairs left behind in garage came in handy to sunning! Accommodations were as described. Five bedrooms made it great for our group to have some private space at the end of the day. You can walk to everything within 2 miles on Anna Maria Island. Only one drawback is the pool is mostly shade for the day. I would definitely rent here again!
Stayed 7 nights in Nov 2021
Verified

10/10 Excellent

Beth H.

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

Christmas week stay

Overall a great property. Checking in/out was very easy. The location is fantastic. The pool is nice, however it was shaded almost all day in December. The kitchen has basics only. Bedrooms were very nice. We wished we had some extra blankets. When we checked in we were informed the house is listed for sale and showings could be scheduled. Luckily that did not happen as we had no idea that was the case. Overall a great experience.
Stayed 6 nights in Dec 2020
Verified

6/10 Okay

Donna T.

Liked: Check-in, location

Home in Holmes Beach

The house was great for the amount of people we had. I was disappointed with the interior of the home. The couches were stained and rugs also had stains. I didn't feel it was clean. I hope they will take care of the issues because the house itself was nice, just needs some work.
Stayed 7 nights in Jun 2022
Verified

8/10 Good

holly a.

Liked: Cleanliness, check-in, communication, location

Excellent location, great host

House is a great layout (bedrooms spread out for some privacy) and is in a perfect location. House is in need of some TLC, nothing major just minor issues. The host is very attentive. We had some issues right after arriving and someone was out immediately to address them which was nice since we arrived on Saturday. We arrived just after hurricane Ian so we were just thrilled to be there even if there were minor issues. We were told we were the last to occupy this house for a bit as it’s being renovated after our stay, excited to see what it’s like after that. We would definitely stay there again bc of the location and good hosts.
Stayed 7 nights in Oct 2022
Verified

4/10 Poor

Michael A.

Liked: Check-in, communication, location

House needs alot of work inside and out.

The house doesn't have things needs when it comes to staying for a week or more and if you have more than 4 people. Outside was over grown around pool area. Doors don't close, needs utensils, floor was soft in window area. Floor peeling up in spots, furniture in terrible. Dining chairs were terrible.
Stayed 7 nights in Oct 2022
Verified

10/10 Excellent

esther z.

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

Great house

Super comfortable. Had everything. Pool was a little disappointing- wasn’t so clean and the hole in the middle of the table was filled with nasty green stuff. The bedrooms and beds were so comfortable. There are many TVs, took us a minute to figure them all out- one in the bunk room never worked as well as one in one of the upstairs rooms. Dishwasher in the kitchen was broken and super annoying to pull out everytime. The fridge was missing all the shelves on the door and the water dispenser was terrible. The house itself was great and roomy. Just needs a little care with a few appliances.
Stayed 9 nights in Apr 2023
Verified

10/10 Excellent

Rebeka P.

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

Great place, close to the beach!

Close to the beach, very spacious and clean. Had more than enough room for 10 with 3 kids! The garage was full of beach toys and beach chairs for the kids. Very nice bonus!
Stayed 7 nights in Aug 2021
Verified

8/10 Good

Emily O.

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

House and location great!

This was our family’s yearly vacation together. It included our grown children and their families. The house was the perfect size to accommodate everyone. The walk to the beach was easy. We rented a golf cart to zip around the island on. We also used it to take all of the chairs, tents, cooler to the beach each day. My only complaints about the house is that it needs some maintenance. The dishwasher needs to be replaced. The bottom rack wouldn’t roll. You literally had to manually lift it out. Sometimes it wouldn’t come on. The buttons seemed broken. The refrigerator needs replacing also. Broken drawer, broken and missing trays on door, water trickles out of dispenser. The door to the small bedroom on third level was jacked and wouldn’t close without slamming it. There were several lightbulbs out throughout the house. Kitchen had tons of spoons, but not even 10 forks or knives. . Easy fix. We bought plastic ones. Pool was not very clean when we arrived. It did storm and the pool is surrounded by palm trees. Lots of debris. Loved the privacy of the pool and the pool deck! The realty company gave me a garage code that didn’t work. When I called about it, they said the keypad doesn’t work and garage had to be closed from the inside. It was great having a garage to keep tents and chairs in everyday. We had a wonderful time, but I noticed that the rates for this house are jumping dramatically for next year. Hopefully the owners will read the reviews and fix what needs fixing.
Verified

4/10 Poor

Matt H.

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

Poorly managed

We arrived Saturday. Got up Sunday morning to make breakfast. Pulled out the skillet. It was absolutely filthfilthy. The crown molding was coming off the walls. Cabinet door fell off when opening. List a whole day of using the pool. Because they had the landscaping company come in. While trimming the trees. They threw all the dead foliage into the pool. So then they had to call the pool cleaner to clean up the mess. The only good thing about this rental was the location. If I were the owner. I would be finding another company to manage the property.
Stayed 7 nights in Jun 2021
Verified

10/10 Excellent

Debbie P.

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

Great Location

We took our children and grandchildren for a week. Everything was nice and clean. Very relaxing and a close walk to the beach. We would consider renting this next year! Perfect for a family of all ages.
Verified

10/10 Excellent

Cameron H.

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

Great place to stay

This is a beautiful home to stay at def recommend only complaints chairs and benches around dinner table we’re very wobbly and flimsy and felt like they was gonna stand and dishwasher was hard to pull out other than that great place and would def stay there again.
Stayed 7 nights in Jan 2021
Verified

10/10 Excellent

Pam M.

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

Best friends reunion

We had a wonderful time and enjoyed the pool, house, and proximity of the beach. Our concern is the furniture in the dining area. The chairs are all broken down. We couldn’t sit on any for fear they would break. The table also seems a little unstable. The home is a great home but the owners need to do some maintenance to the house as it is weathering and showing wear and tear inside.
Verified

10/10 Excellent

Kim S.

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

Relaxing week at the beach

The home was extremely clean upon arrival which put us at ease immediately. It’s a very short walk to the beach and there were a couple of beach chairs, an umbrella, boogie boards and sand toys which made things easier. The kitchen was stocked with only basic tools with a few missing like tongs and a 9x13 pan but we made do. The beds were very comfortable and the showers were hot! One other minor thing: the furniture was wearing a bit and the dining table and chairs need to be replaced, specifically the benches. Overall our stay was wonderful and we would come back!
Stayed 7 nights in Jul 2020