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Kays Landing

Name: Kays Landing - 423
Brand: The Cottages on the Key
SKU: kays-landing-423
Rating: 5.0 (10 reviews)

On Pine Avenue, Heated Pool & Spa, Walk Everywhere!

Bedrooms: 6

Bathrooms: 6 Full

Sleeps: 8

Your private resort—sparkling pool, aqua loungers, and balconies rising above it all.

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Exclusive Amenities Include: ↑↓

Exclusive Amenities Include:
• Located on Pine Avenue in the Heart of AMI
• Private Heated Pool & Spa
• 8 minute walk to the beach & Less than 5 mins to AMI City Pier
• 6 En Suite Bedrooms, 6 Full Baths, 1 Half Bath
• 5 King Beds, 1 Full over Full Bunk Bed, 1 Queen Sleeper Sofa
• Multiple Spacious Balconies & Rooftop Balcony
• Wolf / Subzero Kitchen Appliances, Regular & Keurig Coffee Maker, Dishwasher, Washer & Dryer, and Kitchen Essentials Provided
• Starter Pack of Toiletry Essentials Included - Shampoo, Conditioner, Hand / Face Soap, Body Lotion, & Makeup Wipes
• Starter Pack of Home Essentials Included - Dish Soap, Dish Sponge, Dishwasher Tablets, Laundry Tablets, & Cleaning Wipes
• Beach Towels, Chairs, Cooler, & Caddy Provided
• Outdoor Area Includes Putting Green, Dining Table, Loungers, Seating, & Gas Grill
• Enhanced Cleaning Protocols Provided by our CottageClean Team
• Island Shuttle Transportation Available

Overview ↑↓

Kay’s Landing | Rooftop Deck + Heated Pool & Spa

Why You’ll Love This Home
Wake up to the coastal charm of Anna Maria Island in a home designed for both luxury and play. From a private heated pool with spa and putting green, to panoramic rooftop views of sunrise and sunset, every corner of Kay’s Landing is crafted for memory-making.

‍‍ Perfect For
Multi-family getaways, adult groups, or couples seeking a refined island retreat with room to gather and private spaces to unwind.

️ Imagine This
Start your morning checking out the view on the rooftop deck as the sun rises over the Gulf. Spend afternoons floating in your private heated pool, then challenge friends to a putting contest on the backyard green. Fire up the grill for alfresco dining, stroll just minutes to boutique shops and dining, and finish your day with a glass of wine under a painted Anna Maria sunset.

Where You’ll Sleep
• Bedroom 1: King Bed · Ensuite Bath, TV
• Bedroom 2: King Bed · Ensuite Bath, TV
• Bedroom 3: King Bed · Ensuite Bath, TV
• Bedroom 4: King Bed · Ensuite Bath, TV
• Bedroom 5: King Bed · Full Bath in Den, TV
• Bedroom 6: Full-Over-Full Bunk · Ensuite Bath, TV
• Common Space: Queen Sleeper Sofa · Extra Flexibility

Explore the Area
• 0.4 miles to Anna Maria Beach Access
• 0.5 miles to Pine Avenue boutiques & dining
• 0.7 miles to Anna Maria City Pier & waterfront restaurants
• 1.5 miles to Coquina Beach
• Free island trolley nearby for easy exploring

⌛ Don’t Wait
Kay’s Landing books quickly—especially in peak season. Every reservation includes our CottageClean™ program: a 6-hour deep clean plus 35-point inspection for your total peace of mind.

Need to Know ↑↓

Pool heated November 15 – April 15. This home has stairs—please contact us for alternatives if needed. Starter packs of kitchen and toiletry essentials provided for a seamless first couple of nights.

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Reviews ↑↓

Total reviews: 10

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Review Date: June 30, 2026

"Thank you! Great trip.

Reviewed By: Mark

Response from The Cottages on the Key:
Hi Mark, Thank you so much for your five-star rating! We truly appreciate you choosing to stay with us and are so glad you had a great experience. We hope to have the pleasure of welcoming you back again soon. Warm regards, Guest Services Team

Good stay!

Review Date: May 11, 2026

"Good stay!

Reviewed By: Kristin Chase

The house was excellent, we had an amazing stay.

Review Date: February 17, 2026

"The house was excellent, we had an amazing stay.

Reviewed By: Jenny Scharmer

Beautiful home in a great location.

Review Date: October 2, 2025

"Beautiful home in a great location. Walking distance to restaurants and beach. Loved our trip.

Reviewed By: Bart Krajewski

We had an amazing stay at this home on Anna Maria Island.

Review Date: August 22, 2025

"We had an amazing stay at this home on Anna Maria Island. Was the perfect space for our multi-generational family to find some time away together. The location is superb - right in the heart of the island where we could literally walk next door for our morning coffee. The beach was a short walk down the street and we loved being amongst the businesses of Pine Ave where we had anything we needed close at hand while still being able to enjoy this spacious and well appointed home. Loved that the upstairs had a second sitting room where the teens could hang while the parents and grandparents got to take advantage of the great room where the kitchen, living and dining spaces all opened to each other.

Reviewed By: Todd Makurath

We had 9 adults and the house had plenty of space for all of us to feel comfortable.

Review Date: July 15, 2025

"We had 9 adults and the house had plenty of space for all of us to feel comfortable. The beds were comfortable, and the bedrooms were spacious. I would recommend changing out the bunkbeds for another king size bed though. The kitchen was equipped with plenty of cookware, dinnerware, and utensils. There was a full size grill, which is so nice to a family who cooks most meals. We enjoyed the pool, and the beach was only a short walk. I would recommend to renting a golf cart. We will be back next year. The check in procedures were super easy, and the check out procedures were simple. The rental company staff were very kind! Not only were they friendly and answered all of our questions promptly; they greeted us with very tasty cupcakes welcoming us to the home. We thought the check out time was a little early (but we understand ). It would be nice for check out time to be pushed back until 11 am; we wanted to grab lunch before heading out from vacation, but the restaurants on AMI do not open until 11 am. We really enjoyed the home and our stay in AMI.

Reviewed By: Kimberly Mata

Communication was answered very promptly when questions arose.

Review Date: June 23, 2025

"We visited Kay's Landing for 5 days with friends and 5 kids (11 and under). The location was perfect, close to beaches and shops, and the pool at the house was perfect. The house was clean and easily accommodated our large group. Communication was answered very promptly when questions arose. We would definitely stay at this location again.

Reviewed By: Rebecca Deden

Thanks for the wonderful accommodations.

Review Date: May 5, 2025

"House was amazing, we had concerns with the recovery from hurricane but you couldn't really tell anything had happened while at this home. Mgmt company was great with communication in every way and even let us in a little early which was much appreciated. Check-out was easy, not much to do per instructions. There's a crow or raven or some black bird that comes and steals all your golf balls so if you plan to putt, I'd hide the golf balls when you're done. We saw it grab a ball, take it to the palm tree in the back left and then carry it over towards the roof somewhere. Bird needs a creative nickname, lol. Thanks for the wonderful accommodations.

Reviewed By: Brett Ryder

We absolutely loved our stay at The Cottages on the Keys!

Review Date: April 2, 2025

"We absolutely loved our stay at The Cottages on the Keys! We had 3 generations of our family under one roof so being in the heart of town, walking distance to everything made it easy to get to everything we wanted to do. The house is beautiful and spacious and we spent hours enjoying the pool. The kitchen had everything we needed and being able to do laundry as needed is extra helpful on a beach vacation. We look forward to visiting again and wouldn't want to book any other spot on the island!

Reviewed By: Marissa Silver

The house is very spacious and the pool was a great alternative to the beach.

Review Date: October 2, 2024

"We loved our stay in Anna Maria. The house is brilliantly located for the beaches, shops, and restaurants. Everything is walkable. The house is very spacious and the pool was a great alternative to the beach. Can't wait to come back.

Reviewed By: Nicholas Ashworth

Kays Landing

On Pine Avenue, Heated Pool & Spa, Walk Everywhere!

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Exclusive Amenities Include: ↑↓

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