•
5 reviews
Operated by a Wander partner
Trusted operators, vetted by Wander
🌴 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.
Living Room
1 queen sofa
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
2 full bunk beds
Living Room
1 queen sofa
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
2 full bunk beds
Mary-Kate
•
October 2025
Jason
•
September 2022
Shelly
•
January 2023
Anna Maria Island, FL 34216, US
Anna Maria Island, FL, USThe Ugly Grouper is a laid-back outdoor restaurant on Anna Maria Island serving fresh seafood, especially their signature crispy grouper tacos, paired with live music and island vibes in a fun, family-friendly atmosphere complete with games and a lively bar scene.
Sandbar Seafood + Spirits is an iconic Anna Maria Island beachfront restaurant offering fresh wild-caught seafood and locally-sourced cuisine with the unforgettable experience of dining with your toes in the sand while watching Gulf sunsets, all within a laid-back atmosphere steeped in over a century of coastal charm.
Beach House Waterfront Restaurant offers fresh, locally sourced seafood and farm-to-table dishes in a relaxed, upscale casual setting right on the beach, with stunning Gulf views and unforgettable sunsets. Its climate-friendly outdoor deck and toes-in-the-sand dining create a perfect spot for sun, fun, and feast.
The Waterfront Restaurant offers fresh, locally sourced seafood in a relaxed setting with stunning river or bay views, perfect for enjoying classic dishes and attentive service. Its inviting ambiance blends casual elegance with waterfront charm.
Anna Maria Island Beach Cafe is a casual beachfront dining spot in Holmes Beach where you can enjoy American cuisine with your toes in the sand, complete with Gulf views, tropical cocktails, and nightly live entertainment. Famous for their all-you-can-eat pancakes and fresh fish platters, it's the perfect place to experience island life without breaking the bank.
Ginny's & Jane E's is a charming Anna Maria Island cafe and bakery serving made-from-scratch breakfast and lunch alongside an eclectic collection of local art and coastal gifts, all wrapped in a warm, quirky "Old Florida" atmosphere that keeps visitors coming back.
The Kokonut Hut is a lively tiki bar on Anna Maria Island, serving tropical cocktails and casual grill fare right on the beach. Enjoy generous portions, cheerful service, and stunning sunset views in a relaxed, beachy atmosphere.
Wicked Cantina Bradenton Beach serves fresh Austin-style Tex Mex and American classics with a side of Gulf views, live music, and award-winning margaritas in a lively, family-friendly setting.
The Porch Restaurant on Anna Maria Island offers a cozy, charming atmosphere where fresh, made-from-scratch New American dishes, including top-quality steaks and seafood, are served with warm, attentive service and inviting outdoor porch seating. It’s perfect for relaxed, memorable dining.
Manatee Public Beach offers soft white sands, clear warm waters, and family-friendly amenities like a playground and volleyball courts, making it ideal for energetic families and groups seeking a fun, relaxing beach day with stunning Gulf sunsets.
Robinson Preserve is a sprawling 600-acre coastal sanctuary in Bradenton offering diverse adventures from kayaking through serene mangrove tunnels to climbing the innovative Canopy Zone treetop playground, making it perfect for nature lovers, families, and outdoor enthusiasts of all ages seeking both relaxation and excitement.
Anna Maria Island is a charming Old Florida beach destination offering pristine sandy shores, vibrant waterfront dining, and abundant water activities like kayaking and dolphin-watching tours. Whether you're seeking relaxation on beautiful beaches, exploring quaint shops and historic villages like Cortez, or adventuring through mangrove trails, this island appeals to families, nature lovers, and anyone craving authentic coastal charm.
Step into history at De Soto National Memorial, where scenic trails, living history camps, and ranger-led kayak tours bring the story of early Florida exploration vividly to life. Perfect for history buffs, nature lovers, and families seeking adventure.
Anna Maria Island Beach offers pristine white sands and calm turquoise waters perfect for swimming, sunbathing, and water sports like kayaking and paddleboarding, making it ideal for families, nature lovers, and anyone seeking a relaxing coastal escape.
Palma Sola Botanical Park is a serene 10-acre oasis in Bradenton featuring rare tropical fruits, exotic plants, and native wildlife set along peaceful shell pathways and tranquil lakes—perfect for nature lovers, photographers, and anyone seeking a free, meditative escape into Florida's lush botanical beauty.
Coquina Beach offers a pristine stretch of soft white sand and crystal-clear Gulf waters perfect for swimming, sunbathing, and spotting dolphins and other wildlife, making it an ideal destination for families, couples, and anyone seeking a quintessential Florida beach experience with excellent amenities and water sports opportunities.
Bean Point Beach Access offers a peaceful escape at the northern tip of Anna Maria Island, where visitors can enjoy soft white sands, clear turquoise waters, and stunning Gulf views. It's perfect for nature lovers and those seeking tranquility away from crowded beaches.
50% refund up to 30 days before check-in. No refund after that.
Pets not allowed
No smoking - fees will apply
Events not allowed
Check-in after 4:00 pm
Check-out before 10:00 am
8 guests maximum
| Date | Price (USD, excl. fees and taxes) | Availability |
|---|---|---|
| Sep 2, 2026 | $1883 | Available |
| Sep 3, 2026 | $1984 | Not Available |
| Sep 4, 2026 | $1998 | Not Available |
| Sep 5, 2026 | $1972 | Not Available |
| Sep 6, 2026 | $1916 | Available |
| Sep 7, 2026 | $1804 | Available |
| Sep 8, 2026 | $1748 | Available |
| Sep 9, 2026 | $1748 | Available |
| Sep 10, 2026 | $1728 | Available |
| Sep 11, 2026 | $1583 | Available |
| Sep 12, 2026 | $1488 | Available |
| Sep 13, 2026 | $1518 | Available |
| Sep 14, 2026 | $1518 | Available |
| Sep 15, 2026 | $1518 | Available |
| Sep 16, 2026 | $1518 | Available |
| Sep 17, 2026 | $1548 | Available |
| Sep 18, 2026 | $1578 | Available |
| Sep 19, 2026 | $1564 | Available |
| Sep 20, 2026 | $1519 | Available |
| Sep 21, 2026 | $1519 | Available |
| Sep 22, 2026 | $1550 | Available |
| Sep 23, 2026 | $1564 | Available |
| Sep 24, 2026 | $1548 | Available |
| Sep 25, 2026 | $1548 | Available |
| Sep 26, 2026 | $1534 | Available |
| Sep 27, 2026 | $1459 | Available |
| Sep 28, 2026 | $1429 | Available |
| Sep 29, 2026 | $1429 | Available |
| Sep 30, 2026 | $1459 | Available |
| Oct 1, 2026 | $1504 | Available |
| Oct 2, 2026 | $1906 | Available |
| Oct 3, 2026 | $2253 | Not Available |
| Oct 4, 2026 | $2211 | Not Available |
| Oct 5, 2026 | $2253 | Not Available |
| Oct 6, 2026 | $2294 | Not Available |
| Oct 7, 2026 | $2294 | Not Available |
| Oct 8, 2026 | $2315 | Not Available |
| Oct 9, 2026 | $2336 | Not Available |
| Oct 10, 2026 | $2336 | Available |
| Oct 11, 2026 | $2336 | Available |
| Oct 12, 2026 | $2294 | Available |
| Oct 13, 2026 | $2232 | Available |
| Oct 14, 2026 | $2294 | Available |
| Oct 15, 2026 | $2396 | Not Available |
| Oct 16, 2026 | $2415 | Not Available |
| Oct 17, 2026 | $2396 | Not Available |
| Oct 18, 2026 | $2336 | Not Available |
| Oct 19, 2026 | $2294 | Available |
| Oct 20, 2026 | $2336 | Available |
| Oct 21, 2026 | $2396 | Available |
| Oct 22, 2026 | $2494 | Not Available |
| Oct 23, 2026 | $2493 | Not Available |
| Oct 24, 2026 | $2370 | Not Available |
| Oct 25, 2026 | $2268 | Not Available |
| Oct 26, 2026 | $2208 | Not Available |
| Oct 27, 2026 | $2208 | Not Available |
| Oct 28, 2026 | $2248 | Not Available |
| Oct 29, 2026 | $2287 | Not Available |
| Oct 30, 2026 | $2248 | Not Available |
| Oct 31, 2026 | $2248 | Not Available |
| Nov 1, 2026 | $2308 | Available |
| Nov 2, 2026 | $2329 | Available |
| Nov 3, 2026 | $2370 | Available |
| Nov 4, 2026 | $2431 | Available |
| Nov 5, 2026 | $2470 | Available |
| Nov 6, 2026 | $2532 | Available |
| Nov 7, 2026 | $2532 | Available |
| Nov 8, 2026 | $2470 | Available |
| Nov 9, 2026 | $2348 | Available |
| Nov 10, 2026 | $2287 | Available |
| Nov 11, 2026 | $2349 | Available |
| Nov 12, 2026 | $2410 | Available |
| Nov 13, 2026 | $2450 | Available |
| Nov 14, 2026 | $2389 | Available |
| Nov 15, 2026 | N/A | Not Available |
| Nov 16, 2026 | N/A | Not Available |
| Nov 17, 2026 | N/A | Not Available |
| Nov 18, 2026 | N/A | Not Available |
| Nov 19, 2026 | N/A | Not Available |
| Nov 20, 2026 | N/A | Not Available |
| Nov 21, 2026 | $3577 | Not Available |
| Nov 22, 2026 | $3746 | Not Available |
| Nov 23, 2026 | N/A | Not Available |
| Nov 24, 2026 | N/A | Not Available |
| Nov 25, 2026 | N/A | Not Available |
| Nov 26, 2026 | N/A | Not Available |
| Nov 27, 2026 | N/A | Not Available |
| Nov 28, 2026 | $4249 | Available |
| Nov 29, 2026 | $3221 | Available |
| Nov 30, 2026 | $2415 | Available |
| Dec 1, 2026 | $2456 | Available |