Which Serendipity Stay is Your Perfect Fit?

| October 26, 2021

Whether your idea of vacation is laying by the pool soaking up the rays, or experiencing the adventures and attractions the area has to offer, Serendipity has an incredible selection of luxury beachfront, beach view, and island vacation rental homes. Keep reading to learn more about each of our properties and discover which Serendipity stay is the perfect fit for you!

Cozy Beach Cottages

SunKissed Cottage

2 bedroom | 2 bathroom | 6 guests

SunKissed Cottage is a quaint 2 bedroom/2 bath waterfront stay on Anna Maria Island. Up to six guests can enjoy this stay, with two pull-out sofa chairs in addition to the bedrooms. Additionally, SunKissed Cottage also features an open kitchen with a breakfast bar that adjoins the great room. Enjoy breathtaking views of the Gulf of Mexico, Tampa Bay, the Egmont Key lighthouse, and the Skyway Bridge as you relax in the spacious great room that reflects the neutral, peaceful design of this charming cottage.


2 bedroom | 2 bathroom | 8 guests

This unique, elevated island home is the perfect place to enjoy a little R&R at the beach. Sky can accommodate up to 8 guests with 2 bedrooms, 2 bathrooms, and 2 additional full size beds located on the screened-in sleeping porches. The home has been recently renovated with new features like the beautiful double-sided wood-burning fireplace, an elevator, and an interior spiral staircase that leads to the rooftop. Located on the north end of Anna Maria Island, it is a short walk to the bustling Pine Avenue with great options for shopping and dining, as well as close to the historic Rod and Reel Pier and Anna Maria City Pier.

Bedroom at Sky

Fun in the Sun 


4 bedroom | 4 bathroom | 8 guests

Experience your own private oasis at FantaSea! Featuring 4 bedrooms, 4 bathrooms, a large heated pool, and your own Beach Volleyball Court. Step out the back gate to the Gulf Beaches or explore the island on Bikes, Paddle Boards, Kayak or Golf Cart – all included with your stay! Enjoy the sunrise on the patio with your coffee, or fire up the grill after a volleyball match and a dip in the pool – Your island FantaSea awaits! 

Sand Trap

4 bedroom | 4 bathroom | 8 guests

Sand Trap is a spacious 4 bedroom, 4 bathroom home that is the perfect destination for your beach vacation. This two-story, recently renovated home is beautifully decorated and features an open floor plan, an elevator, and spacious living area located on the second level. The backyard is perfect for entertaining with a covered patio, the heated, saltwater pool, and the gazebo-covered hot tub. You can even play mini-golf in the backyard! Whether you stay in or go out, there’s a little something for everyone.


4 bedroom | 4.5 bathroom | 8 guests

Serendipity is our flagship Beach Front Home, featuring breathtaking 180 degree Gulf Views. The living area has a full size kitchen, great room and dining room in an open floor plan to capture magnificent views of the sunset and azure waters of the Gulf of Mexico. The master bedroom and bath are located on the first floor, with 3 more bedrooms and their private bathrooms on the second floor. Each floor features its own laundry room, and guests love the luxury of the elevator. Golf Cart, Bikes, Paddle Boards and Kayak all included for your enjoyment!

Triple Tail

4 bedroom | 4 bathroom | 8 guests

Watch the Sunshine Skyway bridge light up as the sun sets over Tampa Bay from the comfort of Triple Tail! This home was totally rebuilt from the ground up, adding a huge second story, four bedrooms, four full bathrooms, plus a bonus room! This home has been lovingly decorated with a coastal flair and calming colors. Walk to the Waterfront Restaurant, City Pier, and all of the shops on Pine Avenue, or Take the trolley and explore the full seven miles of Anna Maria Island!

Living Area/Dining Room at Triple Tail

Luxury by the Beach

Serendipity Gulf Front

4 bedroom | 4 bathroom | 8 guests

Constructed almost entirely of heart-pine wood from the Chiles family farm, Serendipity Gulf Front brings a new meaning to “home is where the heart is.” The kitchen features handmade solid wood cabinets, modern Miele dishwasher, quartz countertops, and Sub-Zero refrigerator and freezer. All bedrooms have their own en-suite bathroom, and two of the bedrooms feature their own private beach access. This beachfront coastal gem is close to all Pine Avenue shops, eateries, the Farmers Market, and Piers on the Bay. Serendipity Gulf Front provides the quintessential ambiance for a sunny getaway or blissful daily life.

Cloud 9

4 bedroom | 4.5 bathroom | 8 guests

Cloud 9 is a luxurious beach-front beauty with 4 bedrooms and 4.5 bathrooms. Appropriately named, this home will have you feeling like you’re floating on cloud nine. It is beautifully decorated with a shabby chic flair, and all rooms have been finished with king-sized beds and en suite bathrooms. Enjoy the views of the beach from the heated swimming pool and hot tub, or watch the waves with a cup of coffee at the breakfast bar. You can also explore the island with the use of a golf cart, bicycles, kayaks, and paddle boards that are included with your stay.

Serendipity Deux

4 bedroom | 4.5 bathroom | 8 guests

Our newest property is a stunning, brand-new 4 bedroom, 4 bathroom beachfront home, lovingly named Serendipity Deux. The entire home was professionally designed and decorated with a luxurious, modern edge. The gourmet kitchen features high end finishes and one of a kind features. Walk to the Rod-n-Reel Pier or explore the island with complimentary bikes, paddleboards, or golf cart.

Pool and Beach View at Serendipity Deux

Recent Stories.

theme park couple

Get Ready for Adventure! Theme Parks Near Anna Maria Island

Anna Maria Island is home to wonderful museums & markets, delicious dining, and so much more. But if you are looking to add a little bit of magic during your ...
Read More
Beach Park Walkway

Discover Outdoor Splendors with a Local Guide to Anna Maria Island’s Parks

Anna Maria Island is a veritable paradise with sugar sand beaches and sunny summer days. It is unsurprising that AMI is a hub for vacationers and business travelers. And while ...
Read More

A Foodie’s Paradise: The Best Food On Anna Maria Island

Vacation and time away from the typical day-to-day should be celebrated! And is there any better way to celebrate than with good food? Get ready to plan a delicious getaway ...
Read More

Be the First to Know

Sign up for our Newsletter and be the first to know about our updates and promotions.

We’ll make sure your next vacation is relaxing and fun!

  • This field is for validation purposes and should be left unchanged.