“Calypso” an Anna Maria Island Private Oasis!

neighborhood of Holmes Beach Vacation Rentals
from/per night $315
  • Sleeps 6
  • 2 Bedrooms
  • 2 Bathrooms
  • 1200 sqft.
  • Pets Allowed


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 AMI. The fully stocked kitchen offers Granite countertops with Stainless Steel appliances. The Living Room- as well as both Bedrooms, are equipped with 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, ...

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  • Beach Chairs
  • Deck / Patio
  • Lawn / Garden
  • Outdoor Furniture
  • Porch / Veranda
  • Satellite / Cable
  • Stereo
  • TV
  • Air Conditioning
  • Bed Linens Provided
  • Dryer
  • Hair Dryer
  • Heating
  • Iron & Board
  • Towels Provided
  • Washing Machine
  • Wireless Internet
  • Living Room
  • Parking
  • Telephone
  • Blender
  • Coffee Maker
  • Dishes & Utensils
  • Dishwasher
  • Grill
  • Kitchen
  • Microwave
  • Oven
  • Refrigerator
  • Stove
  • Toaster
  • Heated Pool
  • Pool
  • Private Pool
  • Children welcome
  • Activities / Restaurants Guide
  • Alarm Clock
  • Beach Umbrellas
  • CD Player
  • Cooking Utensils
  • Dining Area
  • Freezer
  • Keyless Entry System
  • Netflix
  • Outdoor Gas Grill

Location Info

Calypso is a short 8 minute walk to the beach. Take your bike or golf cart and it’s just 2 minutes away! There are several excellent restaurants within a 2-5 minute walk.

Rates & Fees

Nightly rates range from $315.00 to $600.00

From To Minimum Stay Nightly Rate
06/15/2024 06/21/2024 7 nights $415.00
07/27/2024 08/02/2024 7 nights $450.00
08/10/2024 08/16/2024 7 nights $420.00
08/17/2024 08/23/2024 7 nights $400.00
08/24/2024 08/30/2024 7 nights $385.00
09/21/2024 09/27/2024 7 nights $345.00
09/28/2024 10/25/2024 7 nights $315.00
10/26/2024 11/15/2024 7 nights $325.00
11/16/2024 11/22/2024 7 nights $325.00
11/23/2024 11/29/2024 7 nights $500.00
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Check-In Time : 04:00 PM
Check-Out Time : 10:00 AM
  • Pet(s) Allowed : Small dogs only, check with Owner
  • Suitable for Children : Parents should supervise children at all times, especially around the pool

General Policies

Owner will provide Guest with a Rental Agreement, outlining the terms of the use of Calypso at Holmes Beach.  

House Rules

Please respect the Town of Holmes Beach 10pm noise ordinance.  You are vacationing in a residential area.  Parking- 2 cars in the driveway only.  No parking on the grass or street.  Pool Heating- In the cooler winter months, the pool pump heater will turn off at 10pm and turn back on at 8:00am. Pumps can become damaged and burn out if the air temp is 20 degrees cooler than the pool temp. As such, it can take some time during the day to reach the desired temp of between 82-84 degrees. In addition, the Town of Holmes Beach has a 10pm noise ordinance which requires that noisy pool pumps be turned off.  

Terms & Conditions

Cancellation Policy

For rentals canceled within 4 weeks of start date, Full Refund For rentals canceled within 3 weeks of start date, 50% Refund For rentals canceled within 2 weeks of start date, No Refund.


(Based on 9 reviews)
- 11/06/2021 -

"Matt November 2021 Had a great week staying at Calypso. The place was beautiful and had everything we needed. Really enjoyed the pool and backyard bar and big screen tv. The location was great. Only 4 blocks to the beach and close to lots of restaurants and shopping. Highly recommended."

- 09/30/2021 -

"Judy September 2021 Loved this place. Very spacious and spotlessly clean. The backyard was a tropical oasis. Although the pool wasn’t huge, it was adorable and the tiki hut was a fun touch. I’ve already recommended this place to some friends who will be staying on the island."

- 08/28/2021 -

"Loved this Place!"

"Megan August 2021 Loved this place! Literally everything about it was absolutely perfect! Let’s start with the pool- so beautiful and so well lit at night. The beds were WONDERFUL. They have all the beach supplies- chairs, umbrella, toys and cart! No need to take anything with you. Kitchen is fully stocked with cups, bowls, plates, utensils, kurig, toaster, mixer etc. Plenty of towels. A stain cordless sweeper came in handy with messy toddlers. Plenty of space and closets. Right down from the ugly grouper. We LOVED it!"

- 08/06/2021 -

"We had an excellent visit. We particularly loved the pool & the landscaping around it, perfect for days that are scorching hot, it’s easy to stay wet in the shade. We rented the golf cart as well and trips to the beach only took 2 or 3 minutes. Would stay here again!"

- 07/05/2021 -

"Our stay at Craig’s cottage met all of our expectations! The house was very clean upon arrival and Craig was very responsive both before and during our stay. The cottage is only a short golf cart ride away from the beach. The cottage is also close to a variety of restaurants and shops. We also loved spending time at the beautiful outdoor area! I would highly recommend to anyone looking to stay on Anna Maria Island!"

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