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Private Home with Private Pool, Spa, and Ping Pong! New Renovations, Close to Be

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Calypso Cottage by Anna Maria Vacations
Private Pool and Spa
Private Pool and Spa
Swim-up Bar and Umbrella
Fully Equipped Kitchen

Reviews

9.0 out of 10
Wonderful
3 bedrooms3 bathroomsSleeps 61590 sq ft

Popular amenities

  • Pool
  • Hot tub
  • Kitchen
  • Washer
  • Dryer
  • Pet friendly

Explore the area

View in a map
Holmes Beach, FL
  • Place, Bradenton Beach
    ‪4 min walk‬
  • Place, Anna Maria Sound
    ‪5 min walk‬
  • Place, Manatee Public Beach
    ‪6 min walk‬
  • Airport, Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
    ‪27 min drive‬

Rooms & beds

3 bedrooms (sleeps 6)

Bedroom 1

1 King Bed

Bedroom 2

1 King Bed

Bedroom 3

2 Twin Beds

3 bathrooms

Bathroom 1

Bathroom 2

Bathroom 3

Spaces

Deck or patio
Kitchen

About this property

Private Home with Private Pool, Spa, and Ping Pong! New Renovations, Close to Be

Calypso Cottage by Anna Maria Vacations
Home in Holmes Beach, Florida
VRC16-000622

Your island vacation starts at Calypso Cottage, a Mediterranean-inspired escape just a short stroll from Holmes Beach’s white sandy beaches on Anna Maria Island! This three-bedroom, three-bath home offers a private pool with a spa, a ping pong table, and tropical outdoor spaces perfect for fun and relaxation. Located in a desirable, vibrant neighborhood near shops and waterfront eateries, Calypso Cottage combines island charm with modern comforts, making it your perfect beachfront getaway.

Highlights
• 5-minute Walk to Holmes Beach
• 3 Bedroom / 3 Bath
• 2 Kings, 2 Twin Beds
• Private pool and heated spa
• Ping pong table
• Dog friendly
• Washer and Dryer
• Close to shops, restaurants, and local attractions for easy exploration
• 2 Parking spaces

Step outdoors into your lush backyard paradise, surrounded by tropical trees. Relax on sun loungers or Adirondacks, take a dip in the private pool or spa, or enjoy outdoor meals at the patio table. The outdoor space is perfect for fun, relaxation, and entertainment. Explore nearby shops, waterfront restaurants, or cruise the island on foot, bike, trolley, or golf cart, all just minutes from your door.

Inside, the home features an inviting open concept living area with a warm color palette, large windows, and tropical decor that brings the island vibe indoors. The fully equipped kitchen offers modern stainless-steel appliances, ample counter space, and everything needed to prepare island-inspired meals. The spacious dining table and tropical views create a perfect setting for family dinners or game nights, while the cozy sofas invite relaxing evenings after a day at the beach.

The primary bedroom offers a plush king-sized bed, a TV, a walk-in closet, and an ensuite bathroom with a walk-in shower and a luxurious tub, your private haven for unwinding. The second bedroom features a king bed, ample space for your vacation gear, and an ensuite bathroom with a walk-in shower. The third bedroom, ideal for kids or extra guests, has two twin beds and a TV. The hall bathroom includes a walk-in shower, and a laundry area with a washer and dryer adds convenience to your stay.

Room Details
• Primary Bedroom: King bed, ensuite bathroom
• Second Bedroom: King bed, ensuite bathroom
• Third Bedroom: Two Twin beds

Right in the heart of Holmes Beach, just around the corner from local favorites like The Feast, Vinny’s Italian Kitchen, and the island’s free trolley stop. This vacation rental provides an in-unit washer and dryer as well as two parking spaces, including one garage space.

Book Calypso Cottage today and experience a relaxing, fun-filled Anna Maria Island vacation! With its private pool, tropical outdoor spaces, proximity to the beach, and vibrant neighborhood, this home offers everything needed for a memorable seaside retreat!


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This property participates in our Professional Linen Program. In Anna Maria Vacation's continuous effort to bring only the best quality experience to our guests, we are proud to offer a professional linen service at this property to better enhance your enjoyment while staying here. This luxury amenity provides you with high quality linens; including bedding, bath towels, wash cloths, and beach towels that are in place and ready for your use upon your arrival. These high-quality linens are washed in a commercial setting using the latest and best technology.

With host approval before check-in, this property accepts dogs only (No cats or other animals are allowed). An additional pet fee will apply. See our Anna Maria Vacations Rental Policies for full details.

Please Remember: "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.
Our prices include all fees. No hidden fees.

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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
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

About the neighborhood

Holmes Beach

Located in Holmes Beach, this vacation home is near the beach. The area's natural beauty can be seen at Bradenton Beach and Bean Point Beach. Traveling with kids? Consider Fish Hole Adventure Golf, or check out an event or a game at LECOM Park. Be sure to check out the area's animals with activities such as game walks and birdwatching.
View more Vacation Homes in Holmes BeachOpens in a new window
Map
Holmes Beach, FL

What's nearby

  • Bradenton Beach - 4 min walk - 0.4 km
  • AMI Paddleboard Adventures - 5 min walk - 0.4 km
  • West Coast Surf Shop - 5 min walk - 0.4 km
  • Anna Maria Sound - 5 min walk - 0.4 km
  • Manatee Public Beach - 6 min walk - 0.6 km

Getting around

  • Sarasota-Bradenton Intl. Airport (SRQ) - 35 min drive

Restaurants

  • ‪The Ugly Grouper - ‬20 min walk
  • ‪Anna Maria Island Beach Cafe - ‬7 min walk
  • ‪Wicked Cantina - ‬4 min drive
  • ‪Smoqehouse - ‬4 min drive
  • ‪Anchor Inn - ‬15 min walk

Frequently asked questions

Does Private Home with Private Pool, Spa, and Ping Pong! New Renovations, Close to Be have a pool?

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

How much does it cost to stay at Private Home with Private Pool, Spa, and Ping Pong! New Renovations, Close to Be?

As of Apr 1, 2026, prices found for a 1-night stay for 2 adults at Private Home with Private Pool, Spa, and Ping Pong! New Renovations, Close to Be on Jun 7, 2026 start from $481, 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 Private Home with Private Pool, Spa, and Ping Pong! New Renovations, Close to Be pet-friendly?

Yes, pets are allowed at this property.

How much is parking?

Onsite parking is available at the property.

What time is check-in at Private Home with Private Pool, Spa, and Ping Pong! New Renovations, Close to Be?

Check-in begins at 4:00 PM.

What time is check-out at Private Home with Private Pool, Spa, and Ping Pong! New Renovations, Close to Be?

Check-out is at 10:00 AM.

Where is Private Home with Private Pool, Spa, and Ping Pong! New Renovations, Close to Be located?

This family-friendly Holmes Beach vacation home is located by the sea, within a 10-minute walk of Anna Maria Sound and Bradenton Beach. Manatee Public Beach and West Coast Surf Shop are also within 10 minutes.

Reviews

9.0

Wonderful

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. 10 out of 16 reviews
Rating 8 - Good. 5 out of 16 reviews
Rating 6 - Okay. 0 out of 16 reviews
Rating 4 - Poor. 1 out of 16 reviews
Rating 2 - Terrible. 0 out of 16 reviews

8.8/10

Cleanliness

9.6/10

Check-in

9.6/10

Communication

9.6/10

Location

9.0/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Heather Z.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a wonderful stay. The pool/hot tub area was one of the nicest we've experienced on the island and the location is super convenient. Communication with the host was excellent and they were super responsive. Highly recommend!
Stayed 7 nights in Mar 2026
From a partner site

10/10 Excellent

April C.

May 2019 Stay

Calypso Cottage was the perfect house for our family! Would highly recommend! Great location.
Verified

8/10 Good

richard p.

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

Another great vacation

Fantastic property we have stayed here several times. Great location to every thing we needed. Only thing i would like to see is the master bed was not comfortable, needs a smart/roku tv in main area, the sleeper sofa has seen better days and the window in eating area facing the pool needs to be repaired, it has not locked in 2 years and now its dangerous for our grand baby. Im sure we will be back next year or even this year.
Stayed 7 nights in Jun 2024
Verified

10/10 Excellent

melissa E.

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

Great place to bring the family…walking distance to the beach

Loved it the whole time…only problem was one of the jets on the hot tub acted wonky when the blower was on and water would fly out. We still utilized it just without the jets blowing.
Stayed 6 nights in May 2022
Verified

10/10 Excellent

kimberly c.

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

Great family vacation.

Nice house, perfect location… rental company extremely responsive..
Stayed 7 nights in May 2022
Verified

10/10 Excellent

Alex C.

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

As described, clean and close to beach.

Great house and location. Just Change bulbs in foyer. Can't see at night when arriving after dark.
Stayed 7 nights in Apr 2022
Verified

4/10 Poor

Eddie B.

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

Not Great!

Arrived late and found every bed had dirty unsanitary linens. It was so bad our youngest begged to sleep in the car after just completing a 7hr trip. You pay a cleaning fee and expect to have a clean place to stay, the property was not as clean as you would expect especially with everything going on, and the pool looked like it hadn't been cleaned in some time. The only real positive about our stay was the management company. They responded to our concerns immediately and had someone address our issues promptly, however, the person who responded did not seem to treat the situation seriously when she arrived and had a very cavalier attitude. The linen situation was taken care of but the whole experience put a damper on the weekend as we had unfit rest upon arrival and spent half a day waiting to get issues taken care of. The property has wonderfull potential as it is set up for entertaining and is in a not bad location, but closer attention needs to be paid to maintenance and house keeping.
Stayed 3 nights in Sep 2021
Verified

8/10 Good

Jim C.

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

Nice place.

We enjoyed our time. Anna Marie Island is a great place.
Stayed 7 nights in Jul 2021
Verified

8/10 Good

Emily F.

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

Family beach trip

The location was pretty good. Easy walk to the beach. Quiet street. The house itself had some issues, woodwork was broken, a giant TV was just sitting in the living room not even plugged in, the pool shut off at the end. We originally rented this last year but due to covid could not go. The island literally closed to visitors so we could not go, and the rental company was pretty difficult to work with. They made us stay with the same house even though we would have 3 extra people (I was pregnant last year, so would have another child this year). In the end it was ok, but I’m not sure we would stay here again.
Stayed 7 nights in Apr 2021
Verified

10/10 Excellent

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

Spring Vacation

Gorgeous property. 5 minute walk to beach . property manager available for any questions we had an resolved all !!!! We definitely will return!!!
Stayed 7 nights in Mar 2021
Verified

8/10 Good

Verified traveler

Liked: Cleanliness, communication, location

Spa/pool and supplies

House was very clean and nice. Hard to get key out of lockbox. We had no extra trash bags or dish towels and no iron. I called and was told there should be a welcoming bag but there wasn’t one. They were very quick to respond but received wrong size trash bags. The pool wasn’t very warm and the spa was unusable. The jet caps were broken off and sprayed water up and over the sides and water was only warm. Told pool boy, who comes at noon and adds chemicals and tells you not to use pool for 3 hours. Ruined 2 days of pool usage, he acted like he knew already about the spa and would put in a work order. Great walking location to beach and stores.
Stayed 7 nights in Mar 2021
Verified

8/10 Good

Emma D.

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

Wonderful Stay In a Great Location

The location was great and the house itself was very clean and wonderful to stay at. A lot of amenities and the beds were very comfortable. The staff was great and helped us along the way. The only reason I give it 4 stars was that we couldn't use the pool after day 2. The pump went out and was making a screeching noise so loud the neighbors came over to complain. I called and they sent the pool company over but they simply turned off the pool which meant no heat. It was sad to hear all the neighbors playing in their pool all day when we couldn't because it was too cold. I think it was just our bad luck, but still a disappointment.
Stayed 8 nights in Dec 2020
Verified

10/10 Excellent

Oscar B.

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

Familiare e riposante

Ottima isola, spiagge eccezionali e la casa a 3 mm dalla spiaggia e giusta per una famiglia che abbia bisogno di 3 stanze e spazzi dentro e fuori
Stayed 8 nights in Aug 2020
Verified

10/10 Excellent

Nereia C.

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

Great Vacation Getaway

This was a great spot for our small family for a one week beach vacation! Great location, a really nice pool (we’re Floridians so we only wish it was heated), and all the amenities. And it was also very clean, which was important to us.
Stayed 7 nights in Jul 2020
Verified

10/10 Excellent

Brett O.

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

Great location

Great property. Had a couple of issues that the property manager handled immediately! Super location!
Stayed 7 nights in Jun 2020
Verified

10/10 Excellent

terrie s.

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

Perfect

We couldn't have found a more perfect location for our stay. Centrally located to everything we wanted, a short 5 minute stroll to the beach, a short 5 minute stroll to the grocery store and restaurants within 5 to 10 minutes in either direction. The home was beautiful and clean and had the basics of everything we needed. We look forward to booking again at the Calypso Cottage on Anna Maria Island.
Stayed 7 nights in Jan 2020

About the host

Hosted by Anna Maria Vacations

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Languages:

English

Premier Host

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