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The 19th Hole

AMI Beach Home, Private Heated Pool & Spa, Putting Green, Walk to Bay & Gulf Beaches

Bedrooms: 3

Bathrooms: 2 Full

Sleeps: 8

Welcome to The 19th Hole! Experience true island living at this beautifully designed Anna Maria Island beach rental.

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Exclusive Amenities Include: ↑↓

• Private Heated Pool & In Ground Spa
• 7-Hole Putting Green
• 1 King Bed, 1 Queen Bed & 4 Twin Beds (Sleeps 8) with linens provided
• Poolside Dining Area & Outdoor Shower
• Private Parking for 4 Cars
• Wine Fridge
• Propane Gas Grill
• 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
• Enhanced cleaning protocols provided by our CottageClean Team

Overview ↑↓

The 19th Hole | AMI Beach Home, Private Heated Pool & Spa, Putting Green, Walk to Bay & Gulf Beaches

Why You’ll Love This Home
Located just a short walk from both the bay and Gulf beaches of Anna Maria Island, The 19th Hole blends island charm with standout outdoor amenities. Spend your mornings by the private heated pool, practice your short game on the 7-hole putting green, or unwind in the in-ground spa after a day exploring Pine Avenue. Inside, the open living space and well-appointed kitchen make it easy to gather, cook, and relax between beach outings. With thoughtful design and space for up to eight guests, this home offers a comfortable setting for both family time and group getaways.

Perfect For
Families and small groups looking for walkable beach access, private outdoor amenities, and proximity to Pine Avenue dining and shopping.

Imagine This
Start the morning with coffee by the pool before making the quick 3-minute walk to the bay beaches for calm water and paddleboarding. Later, visit the Gulf beaches, where wide stretches of sand and clear water invite you to settle in for the day.
In the afternoon, cool off in the private heated pool, enjoy a drink at the swim-up bar, or soak in the in-ground spa. The outdoor wet bar with refrigerator and seating makes it easy to keep refreshments nearby while the group rotates between swimming and putting practice on the 7-hole green.
As evening approaches, stroll over to Pine Avenue for dinner and local shops, or head back to the house to prepare a meal in the gourmet kitchen, complete with stainless steel appliances, wine fridge, and island seating. End the night in the comfortable living area with a movie or quiet conversation before retreating to your private bedroom space.

Where You’ll Sleep
• Bedroom 1: King Bed
• Bedroom 2: Queen Bed
• Bedroom 3: Two Twin-over-Twin Bunk Beds

Accommodates up to 8 guests.

Explore the Area
• 0.3 Miles to Pine Avenue – Boutiques, local restaurants, cafés, and island shopping.
• 0.4 Miles to Anna Maria City Pier – Historic pier with fishing, waterfront views, and casual dining.
• 0.4 Miles to Bayfront Park – Calm bay waters, picnic tables, and views of the Sunshine Skyway Bridge.
• 0.5 Miles to Bean Point – Northern tip beach known for wide shoreline and sunset views.

Don’t Wait
Your reservation includes peace of mind through our CottageClean™ program, featuring a six-hour deep clean and a detailed 35-point inspection prior to arrival.

Need to Know
The pool is heated from November 15th to April 15th. While the heater works to maintain comfortable temperatures, performance can vary during colder weather. We provide starter packs of kitchen and toiletry essentials - making your first couple of nights seamless. Free high speed WiFi. Guests will enjoy a self check-in process and private entrance, offering a smooth and independent arrival experience. Vacation Rental Registration Number VR21-000087.

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Reviews ↑↓

Total reviews: 17

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Review Date: July 17, 2026

"We absolutely loved this place, it was well stocked and well outfitted. The hosts were helpful and nice. And the pool was amazing!

Reviewed By: Sean

Response from The Cottages on the Key:
Hi Sean,
Thank you so much for your wonderful review! We’re thrilled to hear you absolutely loved your stay.
It’s great to know you found the home well stocked and thoughtfully outfitted with everything you needed. We’re also delighted that our team was able to provide helpful service throughout your stay and that the pool was one of your favorite features.
Thank you for choosing to stay with us. We truly appreciate your kind words and hope to have the pleasure of welcoming you back for another memorable getaway!
Warm regards,
Guest Services Team

Review Date: July 6, 2026

"The house was amazing and the communication with the host/management company was great. The backyard area was perfect for hanging out and entertaining. I definitely want to go back.

Reviewed By: Kristi

Response from The Cottages on the Key:
Hi Kristi, Thank you so much for your wonderful review! We’re thrilled to hear you loved the home and that the backyard was the perfect place to relax and spend time together. Creating spaces where guests can unwind and make lasting memories is exactly what we strive for. We also truly appreciate your kind words about our team. Providing responsive communication and a seamless experience from start to finish is something we take great pride in. Thank you again for choosing to stay with us. We’re so happy to hear you’re already looking forward to coming back, and we can’t wait to welcome you for another memorable stay! Warm regards, Guest Services Team

Review Date: July 6, 2026

"We had a wonderful 4th of July here! The property is clean, well stocked, and had fun extras like lots of rafts for the pool. They even left us some cupcakes for my birthday!
We loved the outdoor area with the kitchen and tv. We were able to snack, swim and watch the World Cup while relaxing poolside. And the putting green was an added bonus for my golf obsessed husband.
In addition, we loved the proximity to the beach, bay and shops/ restaurants. You truly did not have to get in the car if you enjoy walking.
The hosts were responsive and patient with all questions we had. Thank you for a wonderful getaway. We would love to return!

Reviewed By: Melissa

Response from The Cottages on the Key:
Hi Melissa,
Thank you so much for your wonderful review! We’re thrilled to hear you had such a memorable Fourth of July getaway with us and that we could be a small part of celebrating your birthday. We’re so glad you enjoyed the cupcakes!
It’s wonderful to know you made the most of the outdoor living space, from relaxing by the pool and watching the World Cup to enjoying the outdoor kitchen and putting green. We love hearing how guests create special memories together, and it sounds like your family did just that.
Thank you again for choosing to stay with us. We’d love to welcome you back for another unforgettable getaway in the future!
Warm regards,
Guest Services Team

Review Date: June 12, 2026

"Very nice property. Very clean. Everything as expected. Remotes had some dead batteries and the beach wagon was a bit beat up but did not dampen our stay.

Reviewed By: Paul

Response from The Cottages on the Key:
Hi Paul, Thank you so much for your review! We’re delighted to hear you found the property clean, comfortable, and exactly as expected. We appreciate you bringing the remote batteries and beach wagon condition to our attention. Feedback like this helps us stay on top of the little details that contribute to a great guest experience. We’re glad these minor issues didn’t take away from your stay, and we truly appreciate you choosing to stay with us. We hope to welcome you back again soon. Warm regards, Guest Services Team

Review Date: June 12, 2026

"We had a great time staying here with our five daughters! There was plenty of room for everyone. We would definitely consider coming back!

Reviewed By: Tamara

Response from The Cottages on the Key:
Hi Tamara,
Thank you so much for your wonderful review! We’re delighted to hear the home was a great fit for your family and that everyone had plenty of room to spread out and enjoy their stay.
Thank you for choosing to stay with us. We’d love to welcome you and your family back for another memorable vacation in the future!
Warm regards,
Guest Services Team

Review Date: May 26, 2026

Reviewed By: Melissa K.

Response from The Cottages on the Key:
Hi Melissa, 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

Review Date: May 26, 2026

"Loved the privacy and seclusion of this rental. The backyard oasis was exactly what we wanted, with the outdoor bar area an added bonus. Interior was a nice open concept with the bedrooms being somewhat away from the main area. The only complain was not having a half bath on the lower level near the pool area.

Reviewed By: Beth

Response from The Cottages on the Key:
Hi Beth, Thank you for your wonderful review! We're delighted to hear that you enjoyed the privacy and seclusion of the property and that the backyard oasis and outdoor bar area were highlights of your stay. It's also great to know that the open-concept layout and bedroom arrangement provided a comfortable and relaxing experience. We appreciate your feedback regarding the lack of a half bath on the lower level near the pool area. Guest comments like yours are valuable as we continually look for ways to improve the guest experience. Thank you for choosing to stay with us. We hope to welcome you back again soon for another relaxing getaway! Regards, The CottageCrew

Had the best stay!

Review Date: March 17, 2026

"Had the best stay!

Reviewed By: Kristina Lester

Nice visit in a great location.

Review Date: February 26, 2026

"Nice visit in a great location. The house has an amazing social area and plenty to do nearby!

Reviewed By: Cole Stephens

Great area and easily walkable to town.

Review Date: February 12, 2026

"Very clean. Well stocked. Host was helpful when we had a power outage during a storm. Great area and easily walkable to town.

Reviewed By: Cree Jones

Property management was extremely responsive.

Review Date: January 26, 2026

"Beautiful home and in a great location. Property management was extremely responsive.

Reviewed By: Ginger Petrat

Property managers were very responsive when we had questions.

Review Date: October 6, 2025

"We had A fabulous time at this property with our adult kids. The pool and putt putt area was great for handing out! Property managers were very responsive when we had questions.

Reviewed By: Timothy Overman

Will definitely plan a return trip.

Review Date: October 6, 2025

"Home was a few blocks from beach as shown, very walkable. The waters on this side of the island were not crystal clear. However, the crystal clear water beaches are very close to drive, probably a 20 minute walk but a very easy drive. Home is family friendly. Pool has a shallow end which was very nice for our little one who came along. Outside bar with fridge & ice maker was very handy. Home was very clean. Host was very fast responding. We enjoy our first visit to Anna Maria Island & this home!! Will definitely plan a return trip.

Reviewed By: Lorna Phillips

Great place to stay. Kids loved the pool and miniature golf.

Review Date: September 15, 2025

"Great place to stay. Kids loved the pool and miniature golf.

Reviewed By: Richard Rodriguez

Beautiful home.

Review Date: August 4, 2025

"Beautiful home. The outside area was great for the kids to play in the pool and mini golf!

Reviewed By: Courtne Kilby

wonderful stay and we will be back

Review Date: May 21, 2025

"wonderful stay and we will be back

Reviewed By: Rebecca Davidson

unique lodging on a very popular island

Review Date: February 24, 2025

"this private, comfortable home is ideally located in the residential area of the canals, within an easy walk to the gulf beachside, the bayside, and into town. Darling backyard with creatively designed pool, and even more creatively designed 7-hole putting green and clubs and balls to enjoy an after-sunset round. unique lodging on a very popular island

Reviewed By: Patricia Charhut

The 19th Hole

AMI Beach Home, Private Heated Pool & Spa, Putting Green, Walk to Bay & Gulf Beaches

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