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Anna Maria Island! All New Remodeled Private Heated Pool + Walk to the Beach! 🌞

Villa near Bradenton Beach in Holmes Beach

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Photo gallery for Anna Maria Island! All New Remodeled Private Heated Pool + Walk to the Beach! 🌞

A pool with a thatched roof and lounge chairs.
A modern living room with a blue sofa set, a wooden coffee table, and a ceiling fan.
A modern kitchen with white cabinets, a stainless steel refrigerator, and a central island with two woven chairs.
A bedroom with a bed, nightstands, a painting, and a view of greenery.
A two-story house with a covered driveway, palm trees, and a golf cart parked in front.

Reviews

10 out of 10
Exceptional

Entire home

2 bedrooms2 bathroomsSleeps 6112 sq m

Popular amenities

  • Pool
  • Kitchen
  • Washer
  • Dryer
  • Pet friendly
  • Free WiFi

Explore the area

View in a map
Holmes Beach, FL
  • Place, Bradenton Beach
    ‪8 min walk‬
  • Place, Holmes Beach Beaches
    ‪17 min walk‬
  • Place, Manatee Public Beach
    ‪2 min drive‬
  • Airport, Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
    ‪36 min drive‬

Room options

About the area

Holmes Beach

Seaside stay .Stay at this Holmes Beach villa and you'll be within half a mile (1 km) of Bradenton Beach and 2 miles (3 km) of Holmes Beach Beaches. Manatee Public Beach and West Coast Surf Shop are also within 2 miles (3 km).
View more Villas in Holmes BeachOpens in a new window

What's nearby

  • Bradenton Beach - 8 min walk - 0.7 km
  • Holmes Beach Beaches - 17 min walk - 1.5 km
  • Manatee Public Beach - 2 min drive - 1.4 km
  • Anna Maria Sound - 3 min drive - 1.8 km
  • West Coast Surf Shop - 3 min drive - 2.1 km

Getting around

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

Restaurants

  • ‪The Sandbar Restaurant - ‬5 min drive
  • ‪Anna Maria Island Beach Cafe - ‬20 min walk
  • ‪The Ugly Grouper - ‬2 min walk
  • ‪Ginny's & Jane E's - ‬5 min drive
  • ‪The Waterfront Restaurant - ‬7 min drive

About this property

Entire place

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

Anna Maria Island! All New Remodeled Private Heated Pool + Walk to the Beach! 🌞

"Calypso" is a Newly remodeled cottage with a lush tropical backyard, which boasts a Private Heated pool with Waterfall, Swim-up Tiki Table, Weber Grill, and New Patio Bar with 55" Outdoor Smart TV! Calypso is outfitted with a very cozy Coastal decor, to make you feel right at home during your stay on Anna Maria Island. The fully stocked kitchen offers white quartz countertops with Stainless Steel appliances. The Living Room- as well as both Bedrooms, are equipped with large Flat screen TV's for your viewing pleasure. The living room/tv area has a Queen size Sleeper sofa, which make this Awesome Villa sleep up to 6 Beachgoers. Driveway Parking for two vehicles. This is a perfect central Holmes Beach location, easy walking distance to several Restaurants, Taverns, shops, and recreational rentals!
* Bedroom 1: King with TV and Ensuite Bath + Private Patio on Floor 1 * Bedroom 2: King with TV + Private Patio on Floor 1 * Living Room: Queen Sleeper Sofa and regular sofa.

Similar properties

A modern kitchen with a central island, white cabinetry, and a view of greenery through the windows.
'chic on the Beach': Anna Maria Island Escape!
Holmes Beach
  • Pool
  • Kitchen
  • Washer
  • Parking included
'chic on the Beach': Anna Maria Island Escape!

Property amenities

Beach

  • Beach nearby
  • Beach loungers
  • Beach towels

Pool/Spa

  • Heated pool
  • Outdoor pool
  • Private pool

Internet

  • Available in the villa: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Blender
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Ice maker
  • Kitchen island
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Spices
  • Stovetop
  • Toaster

Bedrooms

  • 2 bedrooms
  • Bedsheets provided
  • Sofa bed

Bathroom

  • 2 bathrooms
  • Bathtub or shower
  • Hair dryer
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Separate dining area

Entertainment

  • Smart TV with cable/satellite channels
  • Stereo

Outdoor areas

  • Barbecue grill
  • Fenced yard
  • Outdoor furniture
  • Patio

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Desk
  • Desk chair

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • Welcoming dogs only
  • One pet total (up to 20 lbs per pet)

Suitability/Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • Single level property
  • Smooth flooring in public areas
  • Stair-free path to entrance
  • Upper floors accessible by stairs only
  • Well-lit path to entrance
  • Wheelchair-accessible path of travel
  • Smoking not allowed

Services and conveniences

  • Iron/ironing board
  • Phone

Location highlights

  • Near a health/beauty spa
  • Near the marina
  • Near the sea

Things to do

  • Golf
  • Heated pool
  • Basketball nearby
  • Birdwatching nearby
  • Ecotours nearby
  • Fishing nearby
  • Horseback riding nearby
  • Kayaking nearby
  • Motor boating nearby
  • Sailing nearby
  • Snorkeling 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)
  • Deadbolt lock
  • Fire extinguisher

General

  • Double-glazed windows
  • Some LED lighting used
  • Unit size: 1,200 square feet
  • Water-efficient toilets

Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age: 23

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

Rules

*No music outdoors after 10pm *No loud music indoors after 10pm *Pets not allowed on beds or sofas *No parking on the grass
*No diving into the pool *No running around the pool deck *No tampering with pool equipment or temperature settings *Please turn off pool light

Pets

  • Pets are welcome
  • Only dogs are allowed
  • Maximum 1 (weight limit: 20 lbs per pet)
  • Restrictions apply
  • For more information, you can reach out to the property at the number on the booking confirmation
  • Service animals are exempt from fees
  • Note from host: small dogs only. Less than 20 lbs, no cats

Children and extra beds

  • Children are welcome.
  • Note from host: kids should be supervised by the pool at all times

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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadbolt lock
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
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. This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children. If you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, a smoke detector, and a deadbolt lock in each accommodation.

We should mention

  • To make arrangements for your pet, contact the property directly using the information on your booking confirmation.

Property is also known as

Vrbo Property Holmes Beach
Vrbo Property Private vacation home
Vrbo Property Private vacation home Holmes Beach

Frequently asked questions

How close is Anna Maria Island! All New Remodeled Private Heated Pool + Walk to the Beach! 🌞 to the airport?

This villa is 17.6 mi (39-min drive) away from the Sarasota-Bradenton Intl. Airport (SRQ) airport, the closest popular airport to the property.

Does Anna Maria Island! All New Remodeled Private Heated Pool + Walk to the Beach! 🌞 have an airport shuttle?

Airport shuttle services are not available at this villa.

How close is Anna Maria Island! All New Remodeled Private Heated Pool + Walk to the Beach! 🌞 to the beach?

This villa is a short 8-minute walk from Bradenton Beach and 2.6 mi (7-min drive) from Bean Point Beach. Don't forget your sunscreen!

Does Anna Maria Island! All New Remodeled Private Heated Pool + Walk to the Beach! 🌞 offer free breakfast?

This villa does not offer free breakfast.

Is there a casino at Anna Maria Island! All New Remodeled Private Heated Pool + Walk to the Beach! 🌞?

No, there is no casino at this villa.

What time is check-in at Anna Maria Island! All New Remodeled Private Heated Pool + Walk to the Beach! 🌞?

Check-in begins at 4:00 PM.

Is there free parking at Anna Maria Island! All New Remodeled Private Heated Pool + Walk to the Beach! 🌞?

Free parking is not available at this villa.

Does Anna Maria Island! All New Remodeled Private Heated Pool + Walk to the Beach! 🌞 have a pool?

This villa features an outdoor pool.

Does Anna Maria Island! All New Remodeled Private Heated Pool + Walk to the Beach! 🌞 have a spa?

There are no spa services available at this villa.

How close is Anna Maria Island! All New Remodeled Private Heated Pool + Walk to the Beach! 🌞 to downtown Holmes Beach?

This villa is 1 mi away from Holmes Beach.

Anna Maria Island! All New Remodeled Private Heated Pool + Walk to the Beach! 🌞 Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 14 out of 14 reviews
Rating 8 - Good. 0 out of 14 reviews
Rating 6 - Okay. 0 out of 14 reviews
Rating 4 - Poor. 0 out of 14 reviews
Rating 2 - Terrible. 0 out of 14 reviews

10/10

Cleanliness

Reviews

Verified review

10/10 Excellent

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

Calypso

Absolutely excellent place to stay. Will come back. Property manager Craig is amazing!!!
Stayed 7 nights in Aug 2023
Verified review

10/10 Excellent

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

Perfect spot for a couple

Great location. About 8 minutes walk to the beach. Great heated pool. Wery clean and wery private. Lot of food options within a walking distance. Golf cart on site.
Stayed 7 nights in Nov 2023
Verified review

10/10 Excellent

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

Beautiful Home

The villa is beautiful and comfortable. The backyard is a paradise. Also, great location to shops and restaurants. I highly recommend renting the golf cart offered with this home. We had a blast driving it around the island.
Stayed 7 nights in Dec 2023
Verified review

10/10 Excellent

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

Calypso

Very clean house and yard. Perfect set up for a family. Excellent location, right in the middle of the island. You can take golf cart anywhere you want to go. Craig (Host) was very quick to answer any questions we had before and during our stay. We will definitely go back.
Stayed 7 nights in Nov 2023
Verified review

10/10 Excellent

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

October

Perfect set up for 2 couples. From the bedrooms (bath for each) out to the open space - to the beautiful tropical pool area. Like one large open space.
Stayed 7 nights in Oct 2023
Verified review

10/10 Excellent

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

An Absolute Dream

I cannot speak highly enough of Calypso and owner Craig. We had such an amazing time during out stay. Craig was an excellent host, helpful, responsive, and kind. Calypso is exactly as described in the listing and the photos are accurate (although its even better in person!) Anna Maria Island is magical, and Calypso is an excellent place to enjoy AMI. I look forward to another stay in the near future!
Stayed 5 nights in Oct 2022
Verified review

10/10 Excellent

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

Lovely backyard, close to everything

Perfect property for two couples with two master bedrooms. The backyard with pool was very private and lovely, a shame the pool heater had just been repaired so the water was too cold to enjoy. The backyard landscaping was fantastic, extremely private from the neighbors including the other side of the duplex. Craig was very responsive, we genuinely enjoyed our stay at lovely Anna Maria.
Stayed 7 nights in Dec 2023
Verified review

10/10 Excellent

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

Clean, Comfortable & Convenient Location

The property is very nice... clean, comfortable & nicely appointed. Located in the middle of everything but you'll definitely need a car (or golf cart) to get around. If you plan on cooking meals, which we did, you'll have to bring absolutely everything with you, as there isn't even salt & pepper in the house. Otruly enjoyed our stay, spending most of our "home" time in the pool. Highly recommended.
Stayed 7 nights in Aug 2024
Verified review

10/10 Excellent

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

Relaxing week at Calypso cottage!

We loved the property. Except for the tiki umbrella missing from the table in the swimming pool, we'd have never known there was a recent hurricane. Backyard landscaping and pool are beautiful. Beds were comfy, house was very clean, plenty of towels for showers as well as pool. TV with all the channels. Main area (kitchen, dining area, living room) was very spacious and open. Convenient to trolley stops on both sides! There were a couple of things listed that were not at the house (blow dryer, iron and board) and when I inquired with Craig, he very quickly made sure those brand new items arrived at the house less than 24 hours later. Definitely recommend.
Stayed 7 nights in Jan 2025
Verified review

10/10 Excellent

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

Mother Daughter trip

This property was EXACTLY as pictured. The home was clean and had a properly stocked kitchen. I reached out to Craig regarding an issue with the internet and he had a technician sent at MY convenience! The pool was fabulous - it felt like we are at a resort! The beach accessories were in great shape and there was an over abundance of beach chairs. A wagon was provided but we did not use. The use of the golf cart was an extreme bonus! Having it handy at the house when we arrived was wonderful! I would recommend this home to everyone, but then again no one so it is available for my next trip!
Stayed 7 nights in Jun 2024
Verified review

10/10 Excellent

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

Calypso/Craig’s Place

Absolutely fantastic! We’ve traveled to AMI several times and this was probably our favorite property. Plenty of space with all the amenities anyone could need. The pool/yard is a relaxing oasis. The table and shady area of the pool is ideal for drinks, snacks and a bit of respite from the bright sunshine. The landscaping gives you a sense of privacy. The location is ideal, especially if you rent Craig’s golf cart for your stay. Restaurants, shops and beach access are close to the house. (Insider tip…take the golf cart down to the 68th or 70th St beach access points on Gulf Drive. You can park the golf cart 20 feet away from the beach entrances. Very convenient!) Dealing with Craig was a pleasure and drama-free. He’s a very quick responder to messages and questions. Definitely a 5 star host. We hope to book with him again in the very near future. Overall…we give it our highest recommendation. Thanks again, Craig. Aaron, Julie, Ian and Alex.
Stayed 7 nights in May 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful! Great location! Would stay there again! Host was available and quick to respond.
Stayed 7 nights in Jun 2026
Verified review

10/10 Excellent

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

Clean, well-appointed and great location

Enjoyed a relaxing thanksgiving week with my family of three at this well appointed property. House was very clean and well organized with the all of the amenities necessary for a fun filled time in AMI. Location is convenient to all that the island has to offer. Owner was communicative and responsive. Would highly recommend!
Stayed 7 nights in Nov 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
Stayed 7 nights in Apr 2026

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