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The Cottage on Pine - Charming Pine Ave Cottage w/ Heated Pool in the Heart of Anna Maria Island

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Pool
Living area
Living area
Living area
Living area

Reviews

9.8 out of 10
Exceptional
2 bedrooms1 bathroomSleeps 4106.1 sq m

Popular amenities

  • Parking available
  • Pet-friendly
  • Dryer
  • Washer
  • Air conditioning

Explore the area

Map
Anna Maria, FL
  • Anna Maria City Pier
    ‪5 min walk‬
  • Bean Point Beach
    ‪13 min walk‬
  • Anna Maria Beach
    ‪18 min walk‬
  • Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
    ‪33 min drive‬

Rooms & beds

2 bedrooms (sleeps 4)

Bedroom 1

1 King Bed

Bedroom 2

2 Single Beds

1 bathroom

Bathroom 1

Toilet · Shower only

Spaces

Kitchen
Dining area

About this property

The Cottage on Pine - Charming Pine Ave Cottage w/ Heated Pool in the Heart of Anna Maria Island

Welcome to The Cottage on Pine!
On Anna Maria Island (Anna Maria, FL)

After sustaining hurricane damage, this charming Anna Maria Island vacation rental has been fully and professionally restored to code—ensuring a safe, stylish, and comfortable getaway.

Charming Ground-Level Beach Cottage with Heated Pool in the Heart of Anna Maria

HIGHLIGHTS:
- Living & Dining Area: Open-concept space with comfortable seating, a flat-screen TV, and a dining area for gathering and relaxing.
- Bedrooms:
1 King Bedroom: Features a king bed, TV, French doors leading to the backyard, and ample storage with a dresser and closet.
1 Twin Bedroom: Includes two twin beds, TV, dresser, and closet.
- Outdoor Living:
Covered front porch with outdoor seating, perfect for enjoying coastal breezes and morning coffee.
Private fenced-in backyard featuring a heated pool, loungers, chairs, outdoor dining area, grill, and outdoor shower.
- Pet-Friendly: Welcomes your furry family members with prior approval and a paid pet fee, so everyone can enjoy the island getaway!

Laundry:
Washer and dryer located off the covered porch for convenience.

Kitchen:
Stove, Oven, Microwave, Refrigerator/Freezer, Coffeemaker (12 cup & Keurig), Blender, Toaster, Kitchenware

Amenities:
A/C, Heat, Cable Television, Roku, Wireless Internet, Linens, Towels, TV's, Hair Dryers, Iron/Ironing Board

Parking:
Space for 1-2 cars in the private driveway.

Please Note:
This home is conveniently located behind another property, which also serves as our office. Rest assured, all areas designated for this property—such as the private driveway, entrance, fenced-in backyard, and pool—are completely separate and exclusively for your use, ensuring a peaceful and private stay.

Beach Gear Equipment (Provided by VayKLife Gear):
Assorted beach gear items may be onsite but not guaranteed. Every reservation now includes a credit towards personalized beach gear rental included with your stay (chairs, cart, umbrella, bikes, coolers, games, and so much more). Simply make selections prior to your stay and we will have at your home for you!
(The beach gear credit is based on the home size and length of stay, with the exact amount provided after booking when initiating the beach gear reservation process.)

DESCRIPTION:
Your Dream Island Cottage Vacation
Experience the charm and simplicity of island living at The Cottage on Pine, a beautifully renovated beach cottage nestled in the heart of Anna Maria Island. This cozy retreat is ideal for small families, couples, or friends seeking a relaxing getaway steps away from everything Anna Maria has to offer.

Located directly on Pine Avenue, the main street of Anna Maria, this home places you within walking distance of boutique shops, delicious restaurants, and the white sandy beaches of the Gulf of Mexico. For those seeking activities, the nearby community center offers a fitness center, tennis courts, and a playground, adding even more to your vacation experience.

Step inside and discover a warm and inviting interior that blends modern comfort with timeless charm. The cottage boasts designer-inspired decor and luxurious high-end finishes. The fully equipped kitchen features premium Café appliances and everything you need to prepare meals or snacks during your stay. Relax in the living area with a flat-screen TV, or gather for meals in the dining space.

The spacious king bedroom offers French doors that open to a private deck and backyard, creating a peaceful retreat. The second bedroom, with two twin beds, is perfect for additional guests or children. Both bedrooms are thoughtfully designed to ensure comfort and relaxation.

When you're not at the beach, unwind in the private heated pool surrounded by a lush, fenced backyard. The outdoor space includes loungers for sunbathing, a grilling area, and an outdoor shower for post-beach refreshment. The covered front porch provides a charming spot to enjoy your morning coffee or evening cocktail.

Parking is a breeze with room for 1-2 cars in the private driveway, ensuring easy access to your island hideaway.

Prime Location
Situated in the heart of Anna Maria Island, The Cottage on Pine offers unbeatable access to:
- Pine Avenue: Just steps away, explore its boutique shops, quaint cafes, and restaurants.
- Beaches: A short walk to the breathtaking Gulf beaches with their powdery white sand and turquoise waters.
- Community Center: Enjoy fitness facilities, tennis courts, and a playground nearby.

Book Your Stay at The Cottage on Pine
Whether you're strolling along Pine Avenue, lounging by the private pool, or soaking up the sun at the nearby beaches, The Cottage on Pine offers the perfect mix of location, comfort, and charm. Don't wait—book your stay today and experience the magic of Anna Maria Island!

POLICIES:
NO SMOKING.

Pets are welcome with prior approval, provided they meet our pet policy guidelines. We allow a maximum of two pets, each weighing under 65 lbs. A pet fee applies based on the length of your stay: $100 for stays under 4 days, $200 for stays of 4-14 days, and $400 for stays of 15+ days, per pet.

Guest Requirements:
Registered guests must be at least 25 years of age, provide a copy of a valid ID, and be present throughout the entire stay.

Occupancy Limits:
The standard occupancy is two persons per standard bedroom. For additional occupants beyond this limit, a fee of $25 per person, per night, will be charged, up to the maximum allowable occupancy, if applicable.

Quiet Hours:
Quiet hours are from 10:00 PM to 8:00 AM. As this property is located in a residential area, we ask that you respect our neighbors by maintaining a reasonable noise level both during the day and at night. Excessive or unreasonable noise may disrupt the peaceful enjoyment of the neighborhood and is not permitted.

Reservation Policies:
Reservations are typically for 7-night stays, Saturday to Saturday. However, we offer flexible stays with varying minimum night requirements and non-Saturday check-ins and check-outs during most of the year, except for holidays and peak weeks. Please inquire before booking to confirm availability, as changes cannot always be accommodated after booking.

Cleaning and Safety:
All homes, including linens and towels, are cleaned, sanitized, and inspected between guest stays according to industry standards. A starter set of basic amenities, linens, towels, and bedding is provided upon check-in, based on home occupancy. Daily housekeeping and linen services are not included but are available upon request for an additional fee. For stays of 28 days or longer, a mid-stay clean is required and must be scheduled and paid for by the guest.

This home participates in our Professional Linen Program, ensuring high-quality linens and towels are professionally laundered at a commercial facility between each guest's stay. Please note that extra sets are not stored in the home.

Golf Cart Rentals:
Explore the island with ease! After booking, reserve a golf cart through our sister company, Once Upon A Beach Carts, and enjoy an exclusive discount available only to our vacation rental guests.

Baby Equipment Rentals:
Baby equipment is not provided at the home for safety and sanitation purposes. However, we partner with local companies that offer rental services for baby items, including convenient pick-up and drop-off options. Details will be provided at the time of booking, or you may inquire directly for more information.

Pool and Spa (if any):
The pool is heated year-round at no extra charge for guest convenience, with temperatures maintained between 82-85°F to ensure proper chemical balance and cleanliness. Pool heaters and filters do not operate during quiet hours (10:00 PM to 8:00 AM) per local noise ordinances. Please note that cooler ambient temperatures, especially with a 20°F or greater difference between air and water temperatures, may impact the pool heater's effectiveness.

Guests are required to read and follow all posted rules, safety information, and operating instructions.

Property Security and Safety:
This home may be equipped with exterior cameras, such as Ring or Nest, positioned to monitor the front door, driveways, pool equipment, and entry/exit areas of the backyard. These cameras are installed solely to enhance property security, monitor deliveries, and ensure occupancy limits are met. Cameras are not angled toward areas where privacy is expected or assumed.

PAYMENTS:
- 50% of total amount due must be made at time of reservation request to confirm reservation.
- 50% of total amount due must be paid on or before 60 days prior to check-in date.
- Full amount due must be made at time of booking if check in date is within next 60 days.

CANCELLATION POLICY:
Please review the details of our Cancellation Policy page or Terms & Conditions at booking. We encourage you to review as OUR POLICIES HAVE CHANGED as of NOVEMBER 18, 2024.

For Reservations of 20 Days or Less:
Cancellations More Than 60 Days Before Arrival:
- If you cancel all or part of your reservation more than 60 days before your scheduled arrival date, you will receive a refund of your full deposit, minus the non-refundable booking administration (processing) fee that was originally assessed.

Cancellations 60 Days or Less Before Arrival:
- If you cancel all or part of your reservation 60 days or less before your scheduled arrival date, refunds will only be issued for the base rental rate and applicable taxes for nights we are able to rebook, minus the non-refundable booking administration (processing) fee.
- Please note: While we make every effort to rebook the property and issue refunds, we cannot guarantee that the property will be re-rented at the same rate or for the same number of nights originally reserved. For any nights that the property cannot be re-rented, as well as for non-arrivals, late arrivals, early departures, or alterations resulting in a loss of revenue, no refunds or price adjustments will be provided.

For Reservations of 21 Days or More:
Cancellations More Than 180 Days Before Arrival:
- If you cancel all or part of your reservation more than 180 days before your scheduled arrival date, you will receive a full refund of your deposit, minus the non-refundable booking administration (processing) fee that was originally assessed.

Cancellations 180 to 90 Days Before Arrival:
- If you cancel all or part of your reservation between 180 and 90 days prior to arrival, you will receive a refund equal to 25% of the base rental rate and applicable taxes, minus the non-refundable booking administration (processing) fee.

Cancellations 90 Days or Less Before Arrival:
- If you cancel all or part of your reservation 90 days or less before your scheduled arrival date, refunds will only be issued for the base rental rate and applicable taxes for nights we are able to rebook, minus the non-refundable booking administration (processing) fee.
- Please note: While we make every effort to rebook the property and issue refunds, we cannot guarantee that the property will be re-rented at the same rate or for the same number of nights originally reserved. For any nights that the property cannot be re-rented, as well as for non-arrivals, late arrivals, early departures, or alterations resulting in a loss of revenue, no refunds or price adjustments will be provided.

Important Cancellation Policy Information:
The Manager is not responsible for providing refunds due to circumstances beyond their control, including but not limited to travel disruptions, guest travel restrictions, changes in work or school schedules, or similar issues. Additionally, conditions such as weather, tropical storms, hurricane threats, environmental factors (e.g., red tide), construction, water quality, or beach conditions cannot be guaranteed.

Submitting a Cancellation Request:
- All cancellation requests must be initiated by the Registered Guest who booked the reservation.
- Requests must be submitted either through the website where the booking was made or in writing via email.
- Cancellation requests will not be accepted via phone, text, or from any party member other than the Registered Guest.

These policies are in place to ensure clear communication and a smooth process for all guests.

Travel Insurance:
- We continue to offer our U.S. Citizen guests (with the exception of residents of NY and HI) the option of purchasing CSA Travel Insurance directly through us. We strongly encourage all guests to purchase Travel Insurance to protect their vacation investment in the event of any unforeseen circumstances.
- Please note that refunds or credits are not provided for COVID-19-related cancellations, weather, or beach conditions that fall outside of our stated cancellation policy. Additionally, please be aware that hurricane season spans June 1st through November 30th, and Travel Insurance can help safeguard your plans during this period.

In the event the reservation dates fall within a mandatory island evacuation, unforeseen unavailability of the reserved home, the unavailability of a comparable alternative home, or an inability for vacation rentals to operate due to an executive order, the guest will receive a full refund of the base rental rate, applicable fees (excluding the booking administration fee), and all applicable taxes without penalty.

If you have any questions about the cancellation policy or Travel Insurance, please don't hesitate to reach out for clarification.

Max Occupancy: 4
Max Cars: 2
City of Anna Maria: N/A

The information provided online, though deemed accurate is not guaranteed. It is subject to errors, omissions, change of price or withdrawal without notice.

Property manager

Once Upon a Beach Vacation Rentals - Nikki & Mike Kaleta, Owners
Premier Host

Languages

English

Add dates for prices

Amenities

Pool
Kitchen
Washer
Dryer
Pet-friendly
Air conditioning

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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
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock

About the area

Anna Maria

Located in Anna Maria, this holiday home is near theme parks and near the beach. The area's natural beauty can be seen at Bean Point Beach and Anna Maria Beach. AMI Paddleboard Adventures and Fish Hole Adventure Golf are also worth visiting. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
Map
Anna Maria, FL

What's nearby

  • Anna Maria Island Museum and Historical Park - 1 min walk - 0.1 km
  • Anna Maria City Pier - 5 min walk - 0.5 km
  • Island Players - 5 min walk - 0.5 km
  • Bean Point Beach - 13 min walk - 1.2 km
  • Anna Maria Beach - 18 min walk - 1.6 km

Getting around

  • Sarasota, FL (SRQ-Sarasota-Bradenton Intl.) - 33 min drive

Restaurants

  • ‪Anna Maria Island Beach Cafe - ‬6 min drive
  • ‪Rod & Reel Pier - ‬17 min walk
  • ‪Two Scoops - ‬5 min walk
  • ‪Sandbar Seafood & Spirits - ‬8 min walk
  • ‪The Waterfront Restaurant - ‬5 min walk

Frequently asked questions

Does The Cottage on Pine - Charming Pine Ave Cottage w/ Heated Pool in the Heart of Anna Maria Island have a pool?

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

Is The Cottage on Pine - Charming Pine Ave Cottage w/ Heated Pool in the Heart of Anna Maria Island pet-friendly?

Yes, pets are allowed at this property.

What time is check-in at The Cottage on Pine - Charming Pine Ave Cottage w/ Heated Pool in the Heart of Anna Maria Island?

Check-in begins at 4:00 PM.

What time is check-out at The Cottage on Pine - Charming Pine Ave Cottage w/ Heated Pool in the Heart of Anna Maria Island?

Checkout is at 10:00 AM.

Where is The Cottage on Pine - Charming Pine Ave Cottage w/ Heated Pool in the Heart of Anna Maria Island located?

Situated near the beach, this holiday home is within a 15-minute walk of Anna Maria Island Museum and Historical Park and Bean Point Beach. Historic Green Village and Anna Maria City Pier are also within 5 minutes.

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 13 out of 16 reviews
Rating 8 - Good. 3 out of 16 reviews
Rating 6 - Okay. 0 out of 16 reviews
Rating 4 - Poor. 0 out of 16 reviews
Rating 2 - Terrible. 0 out of 16 reviews

9.8/10

Cleanliness

9.8/10

Check-in

10/10

Communication

9.8/10

Location

9.8/10

Listing accuracy

Reviews

10/10 Excellent

Pamela M.

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

Heaven on Earth

This cottage is tucked away on one of the most iconic streets in Anna Maria, so close enough to walk to restaurants, shops, gulf & pier. It's so cozy I'd stay again in a heartbeat
Stayed 28 nights in Mar 2025

10/10 Excellent

Jonathan L.

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

Fantastic Stay

Everything was fantastic. Great property and close to the beach. The process of checking in and out was a breeze and any questions I had were answered immediately. Would recommend anyone to stay here.
Stayed 15 nights in May 2024

10/10 Excellent

Malka R.

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

Great location

This property was nicely renovated. It was the perfect size for us (a couple and two dogs). The backyard was adorable and the pool was beautiful. We also appreciated that the back area was completely fenced in. The location was convenient to all of the restaurants and shops on Pine Ave and we were able to walk everywhere. We would definitely stay here again.
Stayed 3 nights in Jan 2024

8/10 Good

Emily L.

Liked: Cleanliness, check-in, communication, location

Location, location, location

Wish we could have stayed longer. Always enjoy our time in AMI.
Stayed 2 nights in Aug 2023

8/10 Good

Alexandra C.

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

Wonderful Cottage, Great Location

We stumbled upon this cottage while planning a girls trip of four to Anna Maria Island and were immediately sold on the decor and layout of the cottage on Pine (who doesn’t love a pink kitchen?!). Bonus points for the private pool in the back, complete with outdoor shower, putting green and a few little lizard friends roaming around! The space was ideal for our long weekend, conveniently located to shops, restaurants and at a mid-point of the island with easy access to either side of beaches. We opted to rent a cart from Once Upon a Beach and it was already parked in our driveway upon arrival. The amenities of the home were good for what we needed. All the necessities for a beach day were provided (chairs, noodles/floats, umbrella) which was much appreciated! However, the four of us quickly ran through the 4 bath towels provided and there weren’t additional pillows/sheets/blankets should one of us choose to sleep on the couch/had there been a child along for the trip (listing says sleeps 4 adults and up to 2 children, we did not have any with us). Lastly, while we probably chose the hottest week to visit Florida, and we expected some heat, the AC struggled to get down below 75 every night which was uncomfortable. There was a box fan provided with the house so we did utilize that to assist with the air flow. Overall, this cottage was the ideal spot for us on the trip and would highly recommend it to future travelers.
Stayed 4 nights in Aug 2023

10/10 Excellent

Verified traveller

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

Cottage on Pine

Great location and we enjoyed it tremendously
Stayed 5 nights in Jul 2023

10/10 Excellent

Erin G.

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

Clean and great location

The house was the perfect size for our small family. It had everything we needed. Beautifully decorated and very clean! Beds were comfy! Pool area was wonderful! Management company was very attentive and easy to communicate with. Wish the AC could have gone a little lower to cool us off a bit more, but it didn’t bother us too much. We would definitely to go back to this house again!
Stayed 2 nights in Jul 2023

10/10 Excellent

Josh C.

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

Perfect location…

Location location location. Short walk to the Bay or Gulf (5 minutes tops) as well as AMIs go to eateries. The cottage is all a family of 4 needs for a stay on AMI. We live in a fairly large home so the smaller size of the cottage brought us closer together. If I had to be really critical I would say the backyard could use some more shade, perhaps a small tiki hut with shade for 4 chairs or something of that nature. I mention this because the pool water was hot. Again I’m being very critical here but honest. Also, if you are out at night the artificial turf seems to attract mosquitoes so use bug spray if you decide to lounge in the back lawn in the evenings. Aside from that, we would certainly stay here again.
Stayed 6 nights in Jul 2023

10/10 Excellent

Megan p.

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

Great cottage

Had a great stay in the heart of AMI. The cottage was adorable and clean. Great pool and renovation in the back yard. Property management was easily available with anything we needed. Definitely would come back. Thanks!!!
Stayed 3 nights in Mar 2023

10/10 Excellent

Kristen W.

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

Weekend Away

Perfect weekend getaway for my family of three. Amazing location right on Pine Ave. Within walking distance of local restaurants / shops and a short drive to the beach. Despite being on a main road the space was quite and felt very private. The cottage was very clean. My son’s favorite part was the newly installed 3 hole putting green in the backyard. We explored most of the island by renting a golf cart (which I was able to reserve when booking this property). The golf cart was on property when we arrived and provided a fun way to tour the island. Overall a fun weekend with my family.
Stayed 2 nights in Mar 2023

10/10 Excellent

tony t.

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

Great location.

Great property for a smaller group. Close to restaurants, shopping, and beach. Private backyard and nice pool area.
Stayed 7 nights in Nov 2022

10/10 Excellent

Cindy E., Keywest Florida/Flemington Nj

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

Nice Getaway

The cottage had everything we needed for our short trip. We'll be sure to come back soon!!
Stayed 4 nights in Jul 2022

10/10 Excellent

Laura Z.

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

Great rental for our family of four!

We had a wonderful stay at this cottage property! Perfect location to walk to the beach, restaurants and shops. Easy access for fishing, paddle boarding etc. Nice pool to cool off in and pet friendly. Checks all the boxes for small family. Also parking was perfect for our car with jet ski trailer and golf cart! We hope to be back.
Stayed 4 nights in Jul 2022

10/10 Excellent

Verified traveller

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

Cutest Cottage.

Super cute cottage with the best location. Close to great restaurants and shops. Loved the pool in the back. It was perfect for us 3! We will be back for sure!
Stayed 4 nights in May 2022

10/10 Excellent

Heather D., Westerly RI

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

Quick get away

The space was perfect for our family of 3. We had our Moke to get around which was fun. I was concerned with being right in the middle of town there might be a lot of noise but,, there was none. I would recommend this space for a couple or a small family. The only negative I could say is the outside shower and back yard could use some TLC.
Stayed 5 nights in May 2022

8/10 Good

robyn k.

Liked: Cleanliness, check-in, communication, listing accuracy
Disliked: Location

Nice property but be prepared for Anna Maria island

The home was clean and great for a family of 4. It is right on Pine street if that is what you are looking for. One of the things I was not prepared for is how difficult it was to get food! There are very few restaurants offering seating. For the most part, all restaurants are walk up to the window wait in a long line to get your food and bring it home to eat it. I was not prepared for that. We ended up driving off the island to dinner on our 2 nights there. Just not what I was expecting. But if you are okay with this then this cottage is a great place to stay.
Stayed 3 nights in Apr 2022

About the host

Hosted by Once Upon a Beach Vacation Rentals - Nikki & Mike Kaleta, Owners

Host profile image
A world-class island getaway commands a premier island vacation rental experience. Immerse yourself in laid back luxury in one of our pristine vacation rental homes with a local team dedicated to providing exceptional guest experiences from booking through departure. Whether you are looking for an intimate escape for two in one of our beach chic cottages or bringing the entire extended family to stay in one of our large luxury homes, rest assured you will arrive to discover a meticulously cared for home with unique thoughtful amenities, carefully crafted concierge style island information, and always find yourself just steps to the pristine sugary sand beaches and gin clear waters of our island paradise.

As a boutique luxury vacation rental and property management company, Once Upon A Beach prides ourselves on providing an intimate island experience with five-star care and attention to detail in one of the most beautifully quaint beach towns on earth… the place we lovingly call home, Anna Maria Island. Write the next chapter of your vacation story with us and make memories that will last a lifetime.

Languages:

English

Premier Host

They consistently provide great experiences for their guests