AMI PEPPERTREE PARADISE - Cozy Updated Home w/Heated Pool on North End of Island, 2 Houses to Beach!

neighborhood of Anna Maria Vacation Rentals
  • Sleeps 8
  • 3 Bedrooms
  • 2 Bathrooms
  • 1970 sqft.


Welcome to AMI Peppertree Paradise! On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.1970 sq. ftHIGHLIGHTS:- Kitchen, Dining Area, Living w/ TV- 1 King Bedroom w/ TV and Ensuite Full Bath & Walk-In Closet- 1 Queen Bedroom w/ TV- 2 Bunk Beds w/Trundle (5 Twins) & TV- Hall Full Bath- Heated Pool- Enclosed Porch w/Outdoor SeatingKitchen:Stove, Oven, Microwave, Refrigerator/Freezer, Coffeemaker (12 cup), Blender, Crock Pot, Toaster, Kitchenware, Wine/Beverage Cooler, BarOutdoor Area:Enclosed Porch, Heated Private Pool, Grill (Gas), Covered Patio Area w/ Outdoor Dining & Seating, Foot Wash, Outdoor ShowerApproximate Pool Size:18' x 10'Laun...

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  • Beach Chairs
  • Beach Towels
  • Deck / Patio
  • Porch / Veranda
  • Satellite / Cable
  • TV
  • Air Conditioning
  • Bed Linens Provided
  • Dryer
  • Hair Dryer
  • Iron & Board
  • Towels Provided
  • Washing Machine
  • Wireless Internet
  • Internet
  • Living Room
  • Parking
  • Coffee Maker
  • Dishes & Utensils
  • Dishwasher
  • Grill
  • Ice Maker
  • Kitchen
  • Microwave
  • Oven
  • Pantry Items
  • Refrigerator
  • Stove
  • Toaster
  • Heated Pool
  • Outdoor Pool
  • Pool
  • Private Pool
  • Children welcome
  • Luxury
  • Snowbird & Monthly Stay Rental
  • Activities / Restaurants Guide
  • Cooking Utensils
  • Dining Area
  • Freezer
  • Keyless Entry System
  • Outdoor Gas Grill

Location Info

This little town at the northern tip of Anna Maria Island—full-time population 1,800—is beloved for its beachy ambiance, but it isn’t stuck in time. In the last decade, investors have snapped up many humble 1960s-era concrete-block residences and built multi-story mega vacation rental homes in their place. Now, nearly 70 percent of homeowners are rental owners. That means a constant turnover of weeklong visitors, who bicycle or ride their golf carts to scenic Pine Avenue to shop, dine and stroll to the Anna Maria City Pier and the Rod ’N Reel Pier, with their knockout views of the Sunshine Skyway bridge. Venerable institutions like the Island Players community theater, a weekly farmers market, and the Studio at Gulf and Pine art gallery, which its variety of hands-on art classes, help create a sense of community.


Nightly rates range from $400.00 to $1,000.00


About Owner

We are Mike & Nikki Kaleta with Once Upon A Beach Vacation Rentals & Property Management, full-time island residents, and a husband-and-wife team who solely own and operate our boutique luxury vacation rental agency on Anna Maria Island, Florida. We currently manage 30+ throughout the island on behalf of our owners. We relocated here in 2016 after we fell in love with the small town feel of this beach island paradise and built our small business from the ground up with the passion to share this beloved island with others. It is our utmost goal to make every one of our guests instantly feel at home as a 'true local' in one of our unique, pristine, meticulously designed and luxurious accommodations. From small beachside bungalows to sprawling...

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Check-In Time : 10:00 AM
Check-Out Time : 04:00 PM
  • Suitable for Children

General Policies


Max Occupancy: 8

Max Cars: 2
City of Anna Maria: VR16-000281

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

House Rules

*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!Guests do not have access to the ground floor garage.NO PETS. NO SMOKING. Registered Guest must provide copy of ID, be at least 25 years of age and be present throughout entire stay. Standard occupancy is 2 persons per every standard bedroom, an additional occupant fee of $25 per person/per night will be assessed for each occupant over this up to max occupancy, if applicable. Quie...

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Terms & Conditions

Cancellation Policy

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 MARCH 25, 2023. We continue to offer refunds of deposits for cancellations (for stays of 28 days or less) made greater than 60 days to arrival, however all cancellations are now subject to a non-refundable booking admin fee. We continue to offer our US Citizens guests (with exception to residents of NY and HI) the option of purchasing CSA Travel Insurance directly with us. We strongly encourage all guests to purchase Travel Insurance in the event of any unforeseen eventualities. Refunds or credits are not provided for COVID-19 related cancellations, weather or beac...

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(Based on 10 reviews)
- 10/01/2022 -

Great spot for a weekend away

"My friends and I had a wonderful visit. The house is roomy and has everything we needed. The location was also great with an easy walk to the beach. We had a great time!"

Host Reply
Somer: thank you for the feedback! We're thrilled to hear that you had a great visit on Anna Maria at AMI Peppertree Paradise. We would love to host you all again in the future! Thank you for choosing Once Upon A Beach!
- 09/01/2022 -

Amazing & Close to Beach

"This is a really beautiful home only a few doors down from the beach. It is amazing, quiet, clean, relaxing....I can't say enough good things about the people managing the property too. If any little thing is wrong, they are there to fix it quickly. This is our second year of renting from them (different house) and we're looking to find another house for next year. You can't go wrong renting this home, it's really comfortable and so convenient to the beach."

Host Reply
Thank you so much for the feedback, Blake! We are honored that you are a repeat guest and look forward to hosting you again in the future! We thoroughly enjoy having you and your guests - and are thrilled you enjoy AMI Peppertree Paradise!
- 07/01/2022 -

Beach getaway

"Ideal location, comfortable beds, beautiful decor. Plenty of beach chairs, towels provided. There were a few maintenance issues that did not greatly affect our stay. Ideal"

Host Reply
We are so glad that Paula thoroughly enjoyed her stay with us. As she mentioned the home is gorgeously decorated, properly stocked, and have plenty of amenities. The home is just a few houses to the beach so you are literally 3 minutes from your driveway to the white sand beaches of our island by foot! During her stay, we were required to have our yearly inspection through the city for our vacation rental license. While we always typically schedule these when guests are not present... unfortunately due to the city's limitations we were required to conduct that day. A member of our team personally was on site with the inspector while they quickly checked smoke detectors, pool alarms, gates, etc for safety within a few short minutes. The few items that needed addressed like a new battery or tightening a gate were addressed on site that day. These were not items brought reported by or brought to our attention by the guest because they were not issues for them... rather routine items that just needed to be conducted as we are dedicated to safety and ensuring all policies are followed for our guests. Unfortunately, the guest oddly left a subpar star rating for their stay and does not match with the description of their stay. We hope they mistakenly selected 3 stars or are simply unaware that a 3 star rating is actually a major detriment to our home's rating and status. VRBO considers stays rated less than 5 or 4 stars a massive failure to provide a clean, comfortable, and exceptional experience. The guests did provide helpful feedback to us upon departure on some additional items to consider or for us to be aware of so we can further enhance guest stays which we have already reviewed but mentioned they didn't bring to our attention during their stay as they didn't impact them. I do sincerely believe we did provide a wonderful stay for these guests as they described here in this review and believe the star rating doesn't properly reflect this.
- 07/01/2022 -

Phenomenal Place Very Close to Beach

"This property was amazing and had everything we wanted in a house for vacation. It was a very short walk to the beach ... maybe 5 minutes or less. The house was well equipped with everything you need for the beach including chairs, HUGE beach cart, plenty of chairs, boogie boards, and so much more. The pool was very awesome! Half of the pool is under the house for rainy days and it was very clean. Chairs to lay out by the pool were adorned with pillows. The rooms were very spacious and decorated very nicely. The back porch was screened in to keep you from the mosquitoes and was very nice to watch the storms. This section of the beach was never too busy and plenty of space to set up your beach equipment. We could have used a few more items in the kitchen but we made it through the week with no issues at all. The only thing that is quite inconvenient was the door alarm that would not stop buzzing one night. I would suggest putting a child gate at the bottom the stairs or some other safety measure for children. This buzzer was very aggravating as you has to hit a disable button every time you went in and out of the door. If you did not close the door in a few seconds it would loudly buzz. This was not a game changer for our vacation. If you want an awesome house steps from the beach then pick this home. We had an awesome week and will be back!"

Host Reply
Hey John! We are so happy you enjoyed your vacation and AMI Peppertree Paradise! We truly appreciate the feedback and you taking the time to do so! Unfortunately, the door alarms are mandated by the City for child safety and while we could add a baby gate, the alarms also need to be in place. We do thank you for bringing the malfunction concern to our attention so we can ensure to replace the device :) We thank you for choosing to stay with Once Upon A Beach and would welcome you and your guests back any time!!
- 06/01/2022 -

Great location - fantastic access to the beach and pool very welcome

"Had a great comfortable week."

Host Reply
Thank you for your feedback, Tanya! We loved having you all at AMI Peppertree Paradise and welcome you back to stay with Once Upon A Beach any time!
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