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Stay at Kay's Landing on Anna Maria Island—luxury 6-bedroom home with pool, views & beaches!

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A spacious kitchen with a large island, white cabinetry, and pendant lighting. - Stay at Kay's Landing on Anna Maria Island—luxury 6-bedroom home with pool, views & beaches! (Anna Maria)
A two-story house with a balcony, two garage doors, and a staircase leading to the upper level. - Stay at Kay's Landing on Anna Maria Island—luxury 6-bedroom home with pool, views & beaches! (Anna Maria)
A modern living room with white sofas, a wooden coffee table, and pendant lighting. - Stay at Kay's Landing on Anna Maria Island—luxury 6-bedroom home with pool, views & beaches! (Anna Maria)
A spacious kitchen with a large island, modern pendant lights, and a view of the outdoors. - Stay at Kay's Landing on Anna Maria Island—luxury 6-bedroom home with pool, views & beaches! (Anna Maria)
A two-story house with a swimming pool, outdoor furniture, and a balcony. - Stay at Kay's Landing on Anna Maria Island—luxury 6-bedroom home with pool, views & beaches! (Anna Maria)
Close to Anna Maria Beach and Bean Point Beach, Stay at Kay's Landing on Anna Maria Island—luxury 6-bedroom home with pool, views & beaches! provides a water park, a firepit and an arcade/games room. For some rest and relaxation, visit the hot tub. In addition to laundry facilities, guests can connect to free in-room WiFi, with a speed of 100+ Mbps (good for 1–2 people or up to 6 devices).

Reviews

9.8 out of 10
Exceptional

Popular amenities

  • Pool
  • Hot tub
  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi

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About this property

Stay at Kay's Landing on Anna Maria Island—luxury 6-bedroom home with pool, views & beaches!

  • 🌴 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. The primary guest making the reservation must be at least 26 years of age. A rental agreement is required to be signed after booking and prior to check-in. By booking, you acknowledge that you will be required to complete and sign the rental agreement.

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About the area

Located in Anna Maria, this holiday home is in the city centre and near the beach. The area's natural beauty can be seen at Bradenton Beach and Bean Point Beach. Travelling with kids? Consider Fish Hole Adventure Golf and Florida Maritime Museum at Cortez. Discover the area's water adventures with jet skiing and kayaking nearby, or enjoy the great outdoors with horse riding and ecotours. Visit our Anna Maria travel guide
View more Holiday homes in Anna Maria
Map
Anna Maria, FL

What's nearby

  • A small building with an American flag, surrounded by palm trees and a clear blue sky.
    Anna Maria Island Museum and Historical Park
    2 min walk - 0.1 miles
  • A coastal town with a long sandy beach, clear blue ocean, and residential buildings along the shore.
    Bradenton Beach
    8 min walk - 0.5 miles
  • A sunset over a grassy field with a path leading to the water.
    Bean Point Beach
    18 min walk - 1.0 mile
  • Anna Maria City Pier
    6 min walk - 0.4 miles
  • Island Players
    6 min walk - 0.4 miles

Getting around

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

Restaurants

  • The Sandbar Restaurant
    9 min walk
  • Anna Maria Island Beach Cafe
    9 min drive
  • The Ugly Grouper
    6 min drive
  • Ginny's & Jane E's
    8 min walk
  • The Waterfront Restaurant
    4 min walk

Frequently asked questions

Does Stay at Kay's Landing on Anna Maria Island—luxury 6-bedroom home with pool, views & beaches! have a pool?

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

Is Stay at Kay's Landing on Anna Maria Island—luxury 6-bedroom home with pool, views & beaches! pet-friendly?

No, pets are not allowed at this property.

How much is parking at Stay at Kay's Landing on Anna Maria Island—luxury 6-bedroom home with pool, views & beaches!?

On-site parking is available at the property.

What time is check-in at Stay at Kay's Landing on Anna Maria Island—luxury 6-bedroom home with pool, views & beaches!?

Check-in begins at 4:00 PM.

What time is check-out at Stay at Kay's Landing on Anna Maria Island—luxury 6-bedroom home with pool, views & beaches!?

Checkout is at 10:00 AM.

Where is Stay at Kay's Landing on Anna Maria Island—luxury 6-bedroom home with pool, views & beaches! located?

This family-friendly Anna Maria holiday home is located by the sea, within a 10-minute walk of Anna Maria Island Museum and Historical Park and Bradenton Beach. Bean Point Beach and Anna Maria Beach are also within 1 mile (2 km).

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Reviews

Stay at Kay's Landing on Anna Maria Island—luxury 6-bedroom home with pool, views & beaches! Reviews

9.8

Exceptional

9.6

Cleanliness

10

Location
Rating 10 - Excellent. 7 out of 8 reviews
Rating 8 - Good. 1 out of 8 reviews
Rating 6 - Okay. 0 out of 8 reviews
Rating 4 - Poor. 0 out of 8 reviews
Rating 2 - Terrible. 0 out of 8 reviews

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Thank you! Great trip.
Stayed 7 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house was excellent, we had an amazing stay.
Stayed 4 nights in Jan 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful home in a great location. Walking distance to restaurants and beach. Loved our trip.
Stayed 7 nights in Sep 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 4 nights in Jun 2025
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great Location on AMI. Very walkable area. Enough rooms to accommodate all our guests. Decor was up to date. The only negative is that we had issues with the electricity. Oven not working if A/C was running and fans running in rooms. Breakers flipped in several areas. Lights were flickering throughout our stay. The service did reply quickly and were very communicative, but never solved the issues fully. Great Stay Overall!
Stayed 7 nights in Apr 2026
Verified review

10/10 Excellent

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

Annual Family Vacation

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.
Stayed 7 nights in Jun 2025