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

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

Your private resort—sparkling pool, aqua loungers, and balconies rising above it all.
See exactly how close you are—beach just steps away.
From above, your private oasis sparkles in the sun.
Rooftop deck waiting for sunrise coffee and sunset cocktails.
Slip into the warm evening air—lanai lit, waters shimmering, and the night just beginning.

Reviews

10 out of 10
Exceptional
6 bedrooms6+ bathroomsSleeps 8289.5 sq m

Popular amenities

  • Pool
  • Spa pool
  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi

Rooms & beds

6 bedrooms (sleeps 8)

Bedroom 1

1 King Bed

Bedroom 2

1 King Bed

Bedroom 3

1 King Bed

Bedroom 4

1 King Bed

Bedroom 5

1 King Bed

Bedroom 6

1 Single Bunk Bed

Common Space

1 Double Sofa Bed

6 bathrooms, 1 half bathroom

Bathroom 1

Toilet · Shower only

Bathroom 2

Toilet · Shower only

Bathroom 3

Toilet · Shower only

Bathroom 4

Toilet · Shower only

Bathroom 5

Toilet · Shower only

Bathroom 6

Toilet · Shower only

Half Bathroom 7

Toilet · Shower only

Spaces

Deck or patio
Porch or lanai
Kitchen
Balcony
Separate dining area
Dining area

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.

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House Rules

Check in after 4:00 PM
Minimum age to rent: 26
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

No 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 not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
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 in the city centre and near the beach. The area's natural beauty can be seen at Bradenton Beach and Bean Point Beach. Fish Hole Adventure Golf and H2O Watersportz are also worth visiting. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
View more Holiday homes in Anna MariaOpens in a new window
Map
Anna Maria, FL

What's nearby

  • Anna Maria Island Museum and Historical Park - 2 min walk - 0.2 km
  • Anna Maria City Pier - 5 min walk - 0.4 km
  • Island Players - 6 min walk - 0.6 km
  • Bradenton Beach - 8 min walk - 0.7 km
  • Bean Point Beach - 17 min walk - 1.4 km

Getting around

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

Restaurants

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

How much does it cost to stay at Stay at Kay's Landing on Anna Maria Island—luxury 6-bedroom home with pool, views & beaches!?

As of 3 April 2026, prices found for a 1-night stay for 2 adults at Stay at Kay's Landing on Anna Maria Island—luxury 6-bedroom home with pool, views & beaches! on 25 July 2026 start from NZ$4,103, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

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?

Located in the heart of Anna Maria, this holiday home is within a 10-minute walk of Historic Green Village and Bradenton Beach. Bean Point Beach and Anna Maria Beach are also within 1 mile (2 km).

Reviews

10

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. 4 out of 4 reviews
Rating 8 - Good. 0 out of 4 reviews
Rating 6 - Okay. 0 out of 4 reviews
Rating 4 - Poor. 0 out of 4 reviews
Rating 2 - Terrible. 0 out of 4 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Jenny S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house was excellent, we had an amazing stay.
Stayed 4 nights in Jan 2026
Response from VrboOwner on 17 February 2026
Hi Jenny, Thank you so much for your kind words! We’re thrilled to hear the house was excellent and that you had an amazing stay. It truly means a lot to us. We’d love to welcome you back anytime for another great getaway! Regards, The CottageCrew
Verified

10/10 Excellent

bart K.

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
Response from VrboOwner on 2 October 2025
Hi Bart, We’re so glad you loved your stay and enjoyed the home’s location near the beach and restaurants. Thank you for your kind review! Regards, The CottageCrew
Verified

10/10 Excellent

Rebecca D.

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

10/10 Excellent

Kimberly M.

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
Response from VrboOwner on 15 July 2025
Hi Kimberly, Thank you so much for the detailed and thoughtful review! We're glad the home worked well for your group and that you enjoyed the amenities, location, and warm welcome. We appreciate your feedback on the bunk beds and checkout time—it’s noted and truly helpful. We look forward to hosting you again next year! Regards, The CottageCrew

About the host

Hosted by The Cottages on the Key, Inc.

Host profile image

Languages:

English, French, German, Dutch

Premier Host

They consistently provide great experiences for their guests
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