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Caribbean Surf managed by Beach Retreats FL Anna Maria Island

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Spacious secluded backyard oasis
Gorgeous coastal kitchen with plenty of counter and cabinet space
Outdoor patio just off the living room
Spacious king sized room
King sized bedroom

Reviews

9.6 out of 10
Exceptional
3 bedrooms2 bathroomsSleeps 6116.9 sq m

Popular amenities

  • Pool
  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly
  • Free Wi-Fi

Explore the area

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

Rooms & beds

3 bedrooms (sleeps 6)

2 twin beds

2 Single Beds

King bedroom

1 King Bed

King Bedroom with En sutie

1 King Bed

2 bathrooms

Bathroom 2

Toilet · Shower only

En suite

Toilet · Shower only

Spaces

Deck or patio
Kitchen
Garden
Dining area

About this property

Caribbean Surf managed by Beach Retreats FL Anna Maria Island

306 67th Street Unit B Holmes Beach, FL 34217
VRC 19-000277
🏝 Caribbean Surf by Beach Retreats Vacation Rentals

📍 Holmes Beach, Anna Maria Island
🏡 3 Bedrooms | 2 Bathrooms | Sleeps 6 | Private Heated Pool | Pet-Friendly

✨ Your Anna Maria Island Bungalow Retreat ✨
Welcome to Caribbean Surf, a bright and inviting 3-bedroom, 2-bath bungalow just a short stroll from the sugar-white sands of Holmes Beach. With its cozy coastal charm, private heated pool, and family-friendly amenities, this home is the perfect place to relax, unwind, and enjoy everything Anna Maria Island has to offer.

📝​​​​​​​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

Short walk to Holmes Beach

Private heated pool in your own fenced backyard oasis

🐕Pet-friendly + family-friendly yard space (Non refundable pet fee of $125/pet)

Grill, lounge chairs, and beach gear included

Free Wi-Fi, washer/dryer, central A/C

🏡 Inside Your Home

Bedroom 1: King bed + ensuite bath

Bedroom 2: King bed

Bedroom 3: Two twin beds

Spacious living area with flat-screen TV and comfortable seating

Fully equipped kitchen for family meals and island dining nights

🌴 Outdoor Living

Heated pool with sun loungers and tropical landscaping

Private fenced yard — perfect for kids or pets

Grill + outdoor dining area for BBQ nights under the stars

Beach chairs, umbrella, and wagon provided for seaside adventures

🚲 Explore Anna Maria Island

From Caribbean Surf, you're just minutes away from:

The vibrant shops & eateries of Pine Avenue

Local favorites like Ginny's & Jane E's Café and The Sandbar Restaurant

Island adventures: fishing, kayaking, paddleboarding, biking, and dolphin tours

📅 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 2 vehicles

✨ Whether you're lounging poolside, strolling to Holmes Beach, or exploring the island's hidden gems, Caribbean Surf is your perfect home base for an unforgettable Anna Maria Island vacation.

📩 Book now!
🛜 This home features Silicon Travel. With Silicon Travel's firewall place in place, you can prevent internet access to any malicious activity in a Vacation rental home. Any guest device (WebCam, Baby Monitor, etc) can be added for a set time and will be removed automatically upon departure.

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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

Pets allowed
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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 near theme parks 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 horse riding and ecotours nearby.
View more Holiday homes in Holmes BeachOpens in a new window
Map
Holmes Beach, FL

What's nearby

  • Bradenton Beach - 6 min walk - 0.6 km
  • Island Gallery West - 16 min walk - 1.3 km
  • Palmetto Avenue Beach - 18 min walk - 1.6 km
  • Manatee Public Beach - 3 min drive - 2.1 km
  • Holmes Beach Beaches - 6 min drive - 1.8 km

Getting around

  • Sarasota, FL (SRQ-Sarasota-Bradenton Intl.) - 30 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 - ‬5 min drive
  • ‪Ginny's & Jane E's - ‬4 min drive

Frequently asked questions

Is Caribbean Surf managed by Beach Retreats FL Anna Maria Island pet-friendly?

Yes, pets are allowed at this property.

How much does it cost to stay at Caribbean Surf managed by Beach Retreats FL Anna Maria Island?

As of 1 May 2026, prices found for a 1-night stay for 2 adults at Caribbean Surf managed by Beach Retreats FL Anna Maria Island on 27 July 2026 start from NZ$643, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at Caribbean Surf managed by Beach Retreats FL Anna Maria Island?

On-site parking is available at the property.

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

Check-in begins at 4:00 PM.

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

Checkout is at 10:00 AM.

Where is Caribbean Surf managed by Beach Retreats FL Anna Maria Island located?

This family-friendly Holmes Beach holiday home is located by the sea, 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).

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. 51 out of 58 reviews
Rating 8 - Good. 3 out of 58 reviews
Rating 6 - Okay. 1 out of 58 reviews
Rating 4 - Poor. 0 out of 58 reviews
Rating 2 - Terrible. 3 out of 58 reviews

9.2/10

Cleanliness

9.8/10

Check-in

9.6/10

Communication

9.8/10

Location

9.6/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Misty V.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This was a great place for our family!! The location was great- close to the beach and the pool was private and well-maintained. My teenage boys loved it. We would spend half the day at the pool, half at the beach and then wrap up the evening playing games and relaxing. Perfect place for our family :)
Stayed 7 nights in Apr 2026
Verified

10/10 Excellent

Steven S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Our stay @ Carribean Surf was great. Everything at the property was well appointed and convenient. We'll definitely book again!
Stayed 7 nights in Jul 2025
Verified

10/10 Excellent

Veronika T.

Liked: Cleanliness, check-in, communication, location, listing accuracy
A very nice, clean, and cozy house. Exactly as described. Pool was wonderful! Clean and warm! The yard felt very private and inviting with beautiful palm trees and well maintained landscape. Very convenient deck with dining table for 6. Decor is coastal - light and pleasing. Enough towels and supplies. Plenty of good quality dishes, glasses, etc. (including melamine for outdoor eating). A short walk to a beach entry and places to eat/shop. It is a duplex, so if you have neighbors - you will hear them. A very quiet neighborhood. The only noise complains are from construction - guys start banging truck doors, unloading material and hammering at 7 am... Check in instructions and process are top notch. Will not hesitate to stay again for sure!
Stayed 4 nights in Mar 2026
Verified

10/10 Excellent

Eric B.

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

Awesome stay in a beautiful city

Beautiful house very clean great pool, beautiful palm trees very private would go back again for sure.
Stayed 4 nights in Jun 2023
Verified

10/10 Excellent

Brent B.

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

Great property

Clean, location is great, 5+ stars!
Stayed 21 nights in Feb 2022
Verified

10/10 Excellent

Elizabeth J.

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

This was a very beautiful property with all the necessary amenities. We felt right at home.

This property was beautiful. Gorgeous pool and amenities. We highly recommend staying here.
Stayed 7 nights in Jun 2021
Verified

10/10 Excellent

Jean B.

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

Lovely Stay

The house was clean and comfortable. Exactly as described. It is a bit of a walk to shopping on Pine St, but it has easy access to the beach, which makes it well worth it.
Stayed 7 nights in Mar 2025
Verified

10/10 Excellent

Ensley H.

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

Summer Beach after Disney

Wonderful location. Very spacious home. I would highly recommend this property to families wishing to enjoy Holmes Beach and Anna Maria Island.
Stayed 4 nights in Jun 2022
Verified

10/10 Excellent

Rebekah B.

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

Great house and close to the beach

House was perfect - just as pictured. Short walk to the beach, pool was amazing. Easy check in process. Exceeded expectations. Will definately stay here again.
Stayed 7 nights in Apr 2022
Verified

8/10 Good

sarah b.

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

Very nice 4th of July vacation!

Property was just like described. It was very convenient to beach. Very lovely!
Stayed 7 nights in Jun 2022
Verified

10/10 Excellent

Patty H.

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

Fantastic

From check in to check out it was a terrific stay Place was clean, well stocked and perfect location Loved it and will stay here again Patty Hill
Stayed 4 nights in Sep 2021
Verified

10/10 Excellent

Linda W.

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

Great house

We had a great time and loved the house. Have rebooked for 2025.
Stayed 28 nights in Jan 2024
Verified

10/10 Excellent

Kathleen C.

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

Excellent house in a great location

This was a great house with thoughtful amenities. Location was excellent, just two quick blocks to the beach. Ran 4 miles every day - easy to get around. Quick trip to Mote aquarium and Ringling Museum. Pool was a hit for the kids.
Stayed 7 nights in Dec 2022
Verified

10/10 Excellent

Ann F.

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

Fall Break getaway

We had a great time! The house/duplex was very nice and the property managers were prompt with any questions we had. Very convenient to the beach just 2 blocks. (walking) We rented a golf cart to cruise around the island. (highly recommend!)
Stayed 6 nights in Oct 2022
Verified

10/10 Excellent

Linda S.

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

Christmas

Kids loved the heated pool. Had some issues with the pump to heat pool, maintenance fixed it right away, but happened again.
Stayed 9 nights in Dec 2024
Verified

10/10 Excellent

Marlene p.

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

Enjoy

very good
Stayed 5 nights in Sep 2022
Verified

10/10 Excellent

Talia L.

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

Great stay in a wonderful location!

My family and I had a great stay at this property for a long weekend. The home is located two short blocks to the beach and just a couple minutes drive to the shops and restaurants of AMI. Home is really well appointed and has everything you could need in the kitchen as well as plenty of linens and towels. We traveled with two small children and having the beach wagon, extra chairs, umbrellas, and even a high chair/ pack and play were huge perks. Noticed a couple small issues, like the pool lights being out, but other than that the home is 5 stars!
Stayed 3 nights in Oct 2022
Verified

6/10 Okay

Connie L.

Liked: Check-in, communication, location

Holmes beach rental

The property is just ok. Needs a good cleaning. The pool is shaded by too many palm trees. Furniture needs cleaned or replaced. The island is great.
Stayed 7 nights in Feb 2023
Verified

10/10 Excellent

Liz A.

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

Wonderful get away

We had a lovely 5 night stay at the Caribbean Surf property. It was a super quaint beach house with everything we needed. It was well stocked in the kitchen which was important since we cooked several meals there. My husband used the outside grill as well, with great ease and success. It was a fairly short walk to the beach but was made easier by the wagon that was available. The only issue we had during the stay was that the pool was cleaned one day, then the very next day the lawn service team came and blew all the grass and lawn debris back in the pool. We contacted management, however, and it was rectified fairly quickly. It's a lovely home in a lovely location.
Stayed 5 nights in Apr 2025
Verified

10/10 Excellent

Bill B.

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

Unfortunate circumstances I couldn’t attend.

I found myself in the hospital that weekend and period of my rental and therefore couldn’t attend and utilize this wonderful home. It’s seems nice and the communication with staff was excellent.
Stayed 3 nights in Aug 2022
Verified

10/10 Excellent

Amy M.

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

Excellent comfortable home for busy family

This duplex is ideal- esp if you rent bikes and enjoy island time instead of having to drive. And being in northern Holmes beach made it so simple to get what we needed from the tackle store, shops and both sides of the island. Walking to Holmes took minutes; biking to the AMI bay side was so good too- the pier is gone, but the island is still beautiful. We took a relaxing sailing jaunt with TipTop Sailing to Egmont island to explore - saw much wildlife. Def rent bikes and make sure the lights work; the house had everything but helpful to buy extra Pt, TP, zip lock baggies and tin foil if you are cooking. House even had beach chairs and umbrella which were so appreciated! Pool toys too. We visited Roser church and were delighted to hear a familiar voice (Pastor Dirk!) from our former church in NH sharing such an encouraging message of hope in a hurting world; our teens were glued in and so refreshed, on vaca too!
Stayed 6 nights in Jun 2025
Verified

10/10 Excellent

Kevin A.

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

Great Place and Great Management

My wife and I took our 18 month old to AMI/Holmes Beach for a summer beach getaway. The location and neighborhood were perfect for our purposes - the many beach accesses were a short bike ride or walk from the front door and the neighborhood clean, quiet and safe. Not far from the neighborhood were dining options and stores, we rode our bikes we rented virtually everywhere. The home was a nice and spacious duplex unit that felt very private, the backyard pool was truly your own with a nice grill and lounge area. The house was very well stocked with most of what you’d need to prepare meals, including plenty of children's dish ware. The property management company was incredibly helpful with any issues and easy to get in contact with. We will likely be coming back to this same rental property.
Stayed 4 nights in Jun 2022
Verified

2/10 Terrible

Victor S.

Disliked: Cleanliness, communication, listing accuracy

Bad Experience

Location is about the only good experience this location offered. Property needs a deep cleaning, kitchen door handle needs to be replaced my wife cut her hand on it, we had to request to get pool cleaned, landscaping was horrible palm tree limb fell and damaged my truck called manager and was told it would be taking care, 6 month later i was told it was mother nature fault my truck was damaged. Too bad this app does not offer an option to attach photos. also had to take time from my vacation to let contractors in because the pool deck was falling apart.
Stayed 6 nights in Jul 2022
Verified

2/10 Terrible

Shannon T.

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

Do not stay here if you are particular

We loved Anna Maria! But the place is not great. Let's start with what we DID like: The condo had a nice layout. The pool was great (after they cleaned out the green algae we called about). The location is the best thing for sure. The kitchen had everything we needed, and a great refrigerator. What we did NOT like: There were many rooms that had visible mold on the ceiling. The ac vents were constantly dripping and leaving wet spots on the floor. The washer/dryer is entirely too small for a family. It literally fits 3 beach towels and we had to run 3 or more loads a day. The master bedroom bed mattress is the worst I have ever slept on at a vrbo. It had valleys in the mattress. So I assume it is very old. I did not sleep good the whole trip.
Stayed 7 nights in Jul 2024
Verified

2/10 Terrible

Leslie D.

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

Picture of pool is deceiving and home is not well maintained.

Before we arrived we looked on google earth and saw the foilage was overgrown. When asked management co. They said there is sun on north part of pool. That area is in the woodchips and cant lounge. Picture shown IS DECEIVING. Grabbed chairs for beach and they were filled with food and garbage from whoever used them last. Went to put clothes in closet and a dirty high chair was filled with crusty food. Frig made loud cranking noise more and more each day. Mold on ceiling in primary bath. Home was dirty and had to wash stuff before we used it. Home location is awesome but definitely not well maintained and lacked attention to detail.
Stayed 8 nights in Dec 2023

About the host

Hosted by Beach Retreats

Host profile image
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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