Calypso Cottage: Anna Maria Island Pet Friendly Accommodations for Rent Holmes Beach Florida with Pool and 3 Bedrooms 3 Bathrooms Walk to the Beach

Calypso Cottage: Anna Maria Island Pet Friendly Accommodations for Rent Holmes Beach Florida with Pool and 3 Bedrooms 3 Bathrooms Walk to the Beach

Holmes Beach FL pet friendly cottage rental with pool and hot tub plus 3 bedrooms and 3 bathrooms an easy walk to the beach : Calypso Cottage

Vacation Home in Holmes Beach Florida

515 42nd Street
Bedrooms: 3 Bedrooms • Sleeps 6
Bed Arrangements: 2 Twin Bed - 2 King Bed - 1 Sleeper Sofa QUEEN
Bathrooms: 3 Full Bathrooms
Virtual Tour: Calypso Cottage - Virtual Tour
Location Setting: Waterfront - Nearby
Beach Access: Near a Beach
Air Conditioning: Yes
Pool: Pool (Private)
Hot Tub: Hot Tub (Private)
Internet: Internet Access
Television: Cable/Dish TV
Pet Friendly: Yes
Washer/Dryer: Yes
Map of Holmes Beach

Rates & Availability  
(Displayed in USD)

  • Daily Rates from $150 to $750 per night
  • Weekly Rates from $1,050 to $3,500 per week

Already Booked

Property Description

Calypso Cottage

515 42nd St.

Holmes Beach, Fl. 34217


Calypso Cottage is a stylish Mediterranean beach villa with all the finishing touches of what you would expect from an exquisite Anna Maria vacation home. Only a 5 minute stroll to the beach, the focal point has to be the elaborate pool which wraps around the back and side of the house. It includes a spa and in-pool swim up Tiki hut. Surrounding it is lush tropical foliage with beautiful flowing plants and all the privacy you could wish for.

Sleeping includes two Master suites with private bathrooms, large walk-in closets and King beds. The third room has two twin beds and the 3rd bathroom is just outside the door. All rooms have new flat screen HD TV's, new island style furniture, beautiful breadboard on the walls and crown and base moldings. 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 high quality linens 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.

Take the fuss and worry out of packing your private sheets and beach towels knowing that when you arrive to your dream vacation rental, in place are high quality and commercially cleaned luxury bedding, bath towels, wash cloths and beach towels ready for your stay. Eliminate the guessing game, free up luggage space and breathe easy knowing that everything is already taken care of for you. This same philosophy extends even to your departure- nothing to wash, dry, fold or having to fool with trying to squeeze into an already tightly packed suitcase! A fantastic "must have amenity" for your AMI vacation experience.

The location is outstanding. Being right in central Anna Maria Island, you are close to it all- shopping, restaurants, grocery, banks, the trolley, the beach, the bay- it is just perfect! There are two separate recreation rooms off of the pool are. One is a lounging area with table and chairs in the shade and a flat screen TV. The other area has a ping pong table and tiki chairs.

Come enjoy this beautiful Anna Maria Island paradise villa for yourself!


  • On our Professional Linen Service Program
  • New renovation 3 bed/3 bath
  • 2 King, 2 twin beds, Pull out sleeper sofa-Sleeps 6 comfortably
  • Stylish Mediterranean design with Island feel and decorations throughout
  • Fully stocked kitchen with granite counters
  • Exotic over-sized pool, swim-up Tiki hut, spa, bonus covered pool-side lanai, BBQ grill
  • 5 minute stroll to beach-Located on low-traffic street and next to shopping and restaurants
  • Single family home with laundry room (washer and dryer)
  • Flat screen HD TV's, DVD players, IPod Docking Station/Radio, High speed Wireless Internet, PlayStation video games, Rec room with ping pong
  • Dog friendly property for an extra fee (size and breed restrictions apply)


Calypso Cottage has well-furnished bedrooms with the latest designer beach linens. The Master bedroom is huge! The king sized bed is covered in luxurious bedding. In this room you have your own flat screen TV and large walk in closet. The private bath includes a separate tub and shower and a decorative vanity. The second bedroom also has a king sized bed. It is decorated with the colors of the sea. In this room you will also have a flat screen TV and a private bath. The third bedroom is home to 2 twin beds decorated with brightly colored linens. Located just outside of this bedroom is a full bathroom you and your guest's convenience.


The outside of Calypso Cottage might be the most exquisite part of this luxury Mediterranean island villa. There is a newly renovated deluxe pool which starts in the back of the property and wraps all the way around the side of the property- very unique indeed! It includes a spa and in-pool swim up Tiki hut and is nestled in lush tropical foliage full of blossoming flowers and beautiful colors.

With only a short 5 minute stroll to the famous Anna Maria Island sugar sand beaches, you may have a hard time deciding where to relax on this dream vacation! You are also only a 5 minute walk to all the Holmes Beach restaurants, shopping, grocery and drug store.

Also included for your vacation pleasure is a recreation room on the lower lever just off the pool. It has a ping-pong table, dart board and flat screen HD TV.

The only question will be, what do I enjoy next!

Our pools are heated during the months of November through April at no additional charge to our guests. We do not heat the pools during the warmer months of May through October. If you are renting between November and April and you would like to have your pool heated, we kindly ask that you please contact AMV at least 10 days prior to your arrival so that it ensures us ample time to fulfill your request. Pools are heated to a temperature of 82 degrees. However, please be aware that even in Southwest Florida we do occasionally get cold spells that can send the temperatures down into the 30's for a few nights in a row. This will cause the pool water temperature to draw down to in the 70's and a pool pump will automatically shut down if the outside temperature gets too cold. When the weather gets warmer and the pumps are able to re-engage, please be mindful that re-heating of the pool back to 82 degrees may take several days depending on the severity of the cold spell. Ultimately, these situations are beyond our control. Other issues such as severe weather conditions, equipment malfunction, temporary loss of use of equipment or amenities due to maintenance purposes or other items do happen from time to time. All of our pools and pool equipment are closely monitored by the pool companies. For your safety, we kindly ask that the controls not be tampered with -most of the systems are locked for this reason. Due to the island's strict 10pm noise ordinance, the pool heaters will not run overnight. Please remember, outdoor spas are not hot tubs. Please be aware that AMV does not issue refunds based on acts of god. However, please know that in the rare event of pool equipment malfunction during your stay, AMV will do everything in our power to expedite repairs as quickly as possible as we certainly want you to enjoy your heated pool and Florida sunshine to the fullest extent possible!

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. This property requires a 7 night minimum stay as set forth by Holmes Beach’s Land Development Code. Occupancy may not exceed 6.

Activities and Special Interests

This property provides access to the following activities and special interests:

» Beach
» Biking
» Boating
» Canoeing
» Fishing
» Deep Sea Fishing
» Golfing
» Hunting
» State National Parks
» Nightclub and Disco
» Ocean
» Pet Friendly
» Sailing
» Scuba Diving
» Spa
» Surfing
» Fly Fishing
» Wind Surfing
» Hiking
» Family Vacations
» Kayaking

Other Activities and Interests:
Dining, Shopping, Yoga Sessions, Paddle Boarding, Parasailing, Rent a Jetski or Waverunner, Sightseeing, Visit the Marine Lab and Aquarium, Local Farmers Market, Marie Selby Botanical Gardens, Downtown Venice Art Classic, Enjoy Main Street Live, Beach Bistro’s St. Patrick’s Day Parade, Beach’N Food Truck and Music Festival, Spring Fest, Experience Blue, Brews, & BBQs in late April, Stunning Beaches, Kayak Tour, Nature Hike, Rent a Boat to Go Fishing, Incredible Wildlife, Head to the Best Bars in Florida, Unique Boutiques, Easy and Fun Day Trips, Golf Cart Rentals on Anna Maria Island, Visit the Anna Maria Island Historical Museum, South Florida Museum, Bishop Museum of Science and Nature, Florida Maritime Museum

Featured Amenities

» Air Conditioning
» Cable/Dish TV
» Dishwasher
» Grill
» Hot Tub (Private)
» Internet Access
» Pets Allowed
» Pool (Private)
» Washer/Dryer

Property Features

» Ceiling Fan(s)
» Coffee Maker
» Deck/Patio/Porch
» Dishes/Utensils
» Freezer
» Full Kitchen
» Garage
» Ice Maker
» Microwave
» Oven
» Parking
» Refrigerator
» Towels/Linens


» Game Room

Other Property Amenities

Television, Small Dog, Spa, Close to Gulf, Deck Chairs, Linen Service, Ping Pong


Familiare e riposante 2020-08-28

By: Oscar B Trip Date: 2020-08-17
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 --Great island, exceptional beaches and the house 3mm from the beach is right for a family that needs 3 rooms and spaces inside and out -- Thank you for the five-star review! We are so happy you loved our island and our home! We think the beaches are exceptional as well! We hope to welcome you back soon! --Grazie per la recensione a cinque stelle! Siamo così felici che tu abbia amato la nostra isola e la nostra casa! Pensiamo che anche le spiagge siano eccezionali! Speriamo di darti il ​​benvenuto presto!

Great Vacation Getaway 2020-07-25

By: Nereia Cormier Trip Date: 2020-07-11
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. -- Thank you for the five-star review! That is what we strive for! We are so happy that you enjoyed your stay with us at Calypso Cottage. We do heat our pools during the cooler months (October - April) but when the temps are in the 90s and the heat index is 110, we let Mother Nature take her course with the pools. I hope you found it to be refreshing after a day at the beach! We hope to welcome you back as our guests!

Great location 2020-07-16

By: Brett Opaleski Trip Date: 2020-06-06
Great property. Had a couple of issues that the property manager handled immediately! Super location! -- Thank you for leaving Anna Maria Vacations a 5 star review, Brett! We are so happy to hear that you enjoyed your stay and that our Team was able to assist you in a timely manner! We hope to welcome you back in the future when visiting AMI!

Perfect 2020-01-20

By: Terrie Sewell Trip Date: 2020-01-11
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. -- Thank you for the 5★ review, Terrie! We are glad that you enjoyed your stay at Calypso Cottage and the convenient location to shops, restaurants, and the beach! We are happy that this home was clean upon your arrival and had everything you needed! We look forward to welcoming you back to Anna Maria Island for future stays!

Calypso Cottage 2020-01-09

By: Melanie Colwell Trip Date: 2019-12-28
Calypso Cottage was perfect for our family of six. Convenient to so much! The kids loved the pool/spa and the outdoor space was delightful. A lot of playful banter was shared on the chalkboard and many ping pong tournaments were had! The house was cozy and well maintained. Will definitely recommend this property to friends and family. -- Thank you so much for the 5 star review! We are so happy to hear that you and your family of 6 enjoyed your stay and that your kids pool and outdoor area! We look forward to welcoming you back to Anna Maria Island very soon!

May 2019 Stay 2019-06-10

By: April Trip Date: 2019-05-25
Calypso Cottage was the perfect house for our family! Would highly recommend! Great location. -- Thank you for the five star review, April! We're so happy to hear that Calypso Cottage was the perfect house for you and your family! We are happy that you enjoyed the great location, and we hope to have you back!
Perfect Family Christmas Getway! 2019-01-24

By: Pam Rittenhouse Trip Date: 2018-12-22
We stayed Christmas week and Calypso Cottage had everything we needed to have a really wonderful vacation! The house is only 2 blocks from the beach which is beautiful and has a souvenir/convenience store and a beach café--excellent pancakes. The house was immaculate and the furniture in excellent condition. The kitchen was big and the chairs and bedding very very comfy! We took our Boston Terrier and he was a very well-behaved boy! We enjoyed the TV's in all rooms and the pool area and hot tub are just fabulous with plenty of seating. The wrap around the house heated pool is huge (goes to 5 ft) and perfect for someone with little ones since it is really shallow (truly ankle length on the side of the house almost Zero depth entry). The added bonus is the privacy of the foliage around the house and there are 2 rooms off the lounge area next to the pool and one of these rooms has a nice sitting area with big TV and the other room has a ping pong table and chairs-- just like a game room!. There is also a storage room with beach toys and beach chairs/cart. We rented a golf cart to drive around the island. My 8, 23 and 26 year olds loved it and we drove to the beach and to the shopping areas. The weather on Anna Maria island was in the 70's and perfect. You can even walk your dog on the causeways that connect the island to the mainland-- close to the house . Anna Maria vacations staff was outstanding with answering our questions and even sent out their own staff to clean the pool and fix the WI-FI since there was a big storm a few days before we checked in. I am so happy with the excellent service they provided and we will be back again! Thank You to the Owners and to the AMI vacations staff for a beautiful experience and stay in a lovely home!!! -- Thank you for the amazing review, Pam! We are so glad to hear that everything worked out well and appreciate your kindness regarding the issues during your stay. We are very happy everyone enjoyed the property, it's amenities, and the location. We are glad you were also able to experience the area, enjoying pancakes at the beach café, cruising around on the golf cart, and walking your dog along the causeway! We greatly appreciate your kind words and we would love to have you back again as a repeat guest and happy to apply the returning guest discount!

Great Stay! 2018-10-18

By: Briana B. Trip Date: 2018-09-29
We loved our stay at Calypso Cottage!! The size and layout was perfect for our group and the home was so clean when we arrived. We loved the outdoor area and the pool, as well as the abundance of pool and beach supplies available for us to use! Would absolutely stay here again! -- Thank you for the 5 star review, Briana! We're glad to hear you enjoyed the size and layout of Calypso Cottage, as well as, the pool area and beach supplies. We would absolutely love to have you back again!

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