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

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Pool
Master bedroom with King size bed, 43" smart tv and ensuite bathroom
Room
Room
Master bathroom with double sink vanity, tub/shower combo

Reviews

10 out of 10
Exceptional
2 bedrooms2 bathroomsSleeps 61200 sq ft

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Pet friendly

Rooms & beds

2 bedrooms (sleeps 6)

Bedroom 1

1 Double Sofa Bed

Bedroom 2

1 King Bed

Bedroom 3

1 King Bed

2 bathrooms

Bathroom 1

Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer

Bathroom 2

Soap · Towels provided · Bathtub or shower · Toilet · Shampoo · Hair dryer

Spaces

Deck or patio
Kitchen
Separate dining area
Outdoor play area
Dining area

About this property

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.
Our prices include all fees. No hidden fees.

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House Rules

Check in after 4:00 PM
Minimum age to rent: 23
Check out before 10:00 AM
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Children

Children allowed: ages 0-17
Kids should be supervised by the pool at all times
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Events

No events allowed
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Pets

Pets allowed: dogs less than 20 lbs per pet (limit one pet total)
Small dogs only. Less than 20 lbs, no cats
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Smoking

Smoking is not permitted
*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

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

We should mention

This property does not have elevators

About the neighborhood

Holmes Beach

Located in Holmes Beach, this villa is near the beach. The area's natural beauty can be seen at Bradenton Beach and Bean Point Beach. Fish Hole Adventure Golf and H2O Watersportz are also worth visiting. Be sure to check out the area's animals with activities such as game walks and birdwatching.
View more Villas 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 - 8 min walk - 0.7 km
  • Holmes Beach Beaches - 14 min walk - 1.2 km
  • Manatee Public Beach - 2 min drive - 1.4 km
  • AMI Paddleboard Adventures - 2 min drive - 1.8 km

Getting around

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

Restaurants

  • ‪The Ugly Grouper - ‬2 min walk
  • ‪Anna Maria Island Beach Cafe - ‬20 min walk
  • ‪The Sandbar Restaurant - ‬5 min drive
  • ‪Anchor Inn - ‬4 min drive
  • ‪Ginny's & Jane E's - ‬5 min drive

Frequently asked questions

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

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

How much does it cost to stay at Anna Maria Island! All New Remodeled Private Heated Pool + Walk to the Beach! 🌞?

As of Mar 29, 2026, prices found for a 1-night stay for 2 adults at Anna Maria Island! All New Remodeled Private Heated Pool + Walk to the Beach! 🌞 on Jul 4, 2026 start from $555, 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.

Is Anna Maria Island! All New Remodeled Private Heated Pool + Walk to the Beach! 🌞 pet-friendly?

Yes, this property allows dogs (limit 1 total) with a maximum weight of up to 20 lbs per pet. Some restrictions may apply, so please contact the property for more details.

How much is parking?

Onsite parking is available at the property.

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.

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

Check-out is at 10:00 AM.

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

Situated by the sea, this villa is within a 10-minute walk of Island Gallery West and Bradenton Beach. Holmes Beach Beaches and Manatee Public Beach are also within 1 mi (2 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 12 out of 12 reviews
Rating 8 - Good. 0 out of 12 reviews
Rating 6 - Okay. 0 out of 12 reviews
Rating 4 - Poor. 0 out of 12 reviews
Rating 2 - Terrible. 0 out of 12 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

9.8/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Ashleigh K.

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

10/10 Excellent

Timur F.

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

10/10 Excellent

Elizabeth S.

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

10/10 Excellent

Danielle M.

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

10/10 Excellent

Fred F.

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

10/10 Excellent

Tracey Y.

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

10/10 Excellent

Jessica S.

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

10/10 Excellent

Cynthia T.

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

10/10 Excellent

Rhonda O.

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

10/10 Excellent

karen t.

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

10/10 Excellent

Aaron H.

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

10/10 Excellent

Allison S.

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

About the host

Hosted by Craig McLaren

Host profile image

Languages:

English
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