$0
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Home in Anna Maria, Florida

4 bedrooms

4 beds

4 bathrooms

8 guests

1000 sq. ft.

Luxury

Elevated properties with standout design

Operated by a Wander partner

Trusted operators, vetted by Wander

About the property

Wake up to the sound of waves and step straight onto the sugar-white sands of Anna Maria Island. Serendipity Gulf is your private beachfront sanctuary on the coveted north end—where relaxed bohemian style meets unforgettable Gulf views.

Just completed: a stunning beachside heated pool, perfectly positioned for sun-soaked afternoons and sunset swims with the Gulf as your backdrop.

Gulf Beach Front 3 bedroom/3 bathroom home and separate 1/1 cottage Sunset's from your back deck and morning shell searches out your back door. All bedrooms are King Bed en-suite. Thoughtfully refreshed with all-new flooring and a beautifully redesigned kitchen with brand-new appliances, this home blends comfort, style, and effortless coastal living. The bright, airy interior draws your eyes straight through sliding glass doors to the turquoise waters beyond

Serendipity Gulfront provides a complimentary 6-passenger Golf Cart, perfect for exploring the island. For exploring further, the free island trolley provides convenient transportation, with a stop located right on Pine Ave. Free parking is available on the premises and on the street. The closest major airport is approximately a 1-hour drive away.

Please review and agree to the Reservation Agreement.
Rates and Availability are subject to change until reservation is completed. A deposit must be received in order to reserve the dates you desire.

Pets- Non-Aggressive breeds, vaccinated & current on a flea prevention program allowed only with prior approval.
Pet Fee and Pet Waiver Required. $300 per pet
Any unauthorized pets= 25% surcharge

Traveler must provide photo ID and guest list If for some reason the property you booked is unavailable, we may offer to rebook the Traveler at another property, if a substantially similar property is available for the same period and under a new reservation. Owner is not responsible for events beyond our control, ie: inclement weather, storms, evacuations, etc. Travel Insurance is recommended and may be purchased independently from several sites (Red Sky Travel Insurance, Square Mouth, etc.)

Due to the extensive equipment provided at the home, there are additional documents required.
The use of the bikes, SUP and Kayak require a signed Equipment Waiver for anyone 18+

All Drivers of the property's Golf Cart must be 25, and provide a copy of a valid U.S. Driver's License and Insurance.

We give our guests space to relax but are always available if needed! You’ll receive a personal smart lock code before check-in, and we’re just a message, call, or email away if you have any questions or need anything during your stay. For direct support, contact our office phone.

Amenities

Common Amenities

  • Free parking
  • Paddle board
  • BBQ Area
  • Cleaning supplies
  • Dishwasher
  • Shower
  • Hair dryer
  • Toilet
  • Bedroom door lock
  • Wine Cellar
  • Pet relief area
  • Balcony
  • Water slide
  • Hike trail nearby
  • Beachfront
  • Boat
  • Bay views
  • Private Chef
  • Fishing Area
  • Golf Course
  • First aid kit
  • Fire extinguisher
  • Air conditioning
  • Hot water
  • Washer
  • Carbon monoxide detector
  • Dryer
  • Beach
  • Beach View
  • Children’s dinnerware
  • Cleaning Disinfection
  • Cleaning products
  • Enhanced cleaning practices
  • Essentials
  • Family/kid friendly
  • Fishing
  • Golf - Optional
  • High touch surfaces disinfected
  • Horseback Riding
  • Pets allowed
  • Private entrance
  • Shopping
  • Single level home
  • Suitable for children (2-12 years)
  • Suitable for events
  • Suitable for infants (under 2 years)
  • Water Sports
  • Water View
  • Gym
  • Tennis court
  • Children dinnerware
  • Pack n play
  • Books
  • Basketball Court
  • Massage table
  • Heated pool
  • Laundromat nearby
  • Ironing board

Bathroom 1

  • Bathtub
  • Shower gel

Bathroom 2

  • Body soap
  • Bath linens

Bathroom 3

  • Conditioner

Bathroom 4

  • Shampoo

Patio

  • BBQ Utensils
  • Outdoor seating
  • Patio

Kitchen

  • Baking sheet
  • Blender
  • Coffee
  • Coffee maker
  • Cooking basics
  • Dishes
  • Freezer
  • Ice maker
  • Kettle
  • Kitchen
  • Microwave
  • Mini fridge
  • Oven
  • Fridge
  • Stove
  • Toaster
  • Wine glasses

Exterior

  • Beach access
  • Beach essentials
  • Kayaks
  • Ocean view
  • Waterfront

Garage

  • Bicycle
  • Garage

Living room

  • Board games
  • Ceiling fan
  • Heating
  • TV

Playground

  • Toys

Dining room

  • Dining table
  • High chair

Garden

  • Garden

Pool

  • Hot tub
  • Outdoor pool

Common area

  • Wifi
  • Long term stays allowed
  • Smoke detector

Laundry room

  • Iron

Office

  • Dedicated workspace

Entry

  • Luggage drop off allowed

Bedroom 1

  • Bed linens
  • Hangers

Bedroom 2

  • Closet
  • Safe

Bedroom 3

  • Crib

Bedroom 4

  • Extra pillows

4.9 · 158 reviews

A

Anonymous

This week

Absolutely amazing stay! The house exceeded our expectations. Everything was extremely clean, well maintained, and fully equipped, with so many thoughtful extras that made our stay even more enjoyable. The best part was definitely the location the backyard opens directly onto the beach, so you can literally step outside and have the sand and ocean right there. Having a private pool and hot tub as well made the experience even better. The house itself is beautiful, spacious, comfortable, and has everything you could possibly need for a great family vacation. You can tell a lot of thought has gone into making guests feel at home. We would absolutely stay here again and highly recommend it. Easily one of the best Airbnb experiences we’ve had!
A

Anonymous

July 2026

We had a wonderful family stay at Serendipity. Right on the beach and also convenient to walk or take golf cart to shops and restaurants. The house was beautiful and had plenty of room for our family of 5. Will definitely stay here when we return!
A

Anonymous

July 2026

This house was amazing! Not only was it a beautifully decorated but the location was terrific! A quick walk out the back gate and your right on the beach. The inside was cozy, clean, with nice furnishings that match the beach vibe. The kitchen had everything you needed if you want to cook a full meal. Honestly, I could have moved in. I found myself sitting by the back window every morning reading and looking out at the Gulf.. The back yard is private with it's own pool and a BBQ. The outdoor shower was key! I'll keep dreaming about my next visit to Anna Maria Island!

Where you’ll be

Anna Maria, Florida 34216, United States of America

Anna Maria, Florida, United States of America
27.53381729-82.74278259
Timezone: America/New_York

Restaurants

The Ugly Grouper

The Ugly Grouper offers a lively dining experience with fresh seafood, American favorites, and a vibrant atmosphere featuring live music and outdoor seating. Enjoy a relaxed meal amidst a fun, laid-back setting on Anna Maria Island.

Anna Maria Island Beach Cafe

Anna Maria Island Beach Cafe offers casual dining with stunning Gulf views, featuring all-you-can-eat pancakes and Friday fish fries. Enjoy live music and beach activities alongside delicious meals.

Sandbar Seafood + Spirits

Sandbar Seafood + Spirits offers fresh Gulf-to-table seafood and local organic dishes in a relaxed beachfront setting where you can dine with your toes in the sand while enjoying breathtaking sunsets over the Gulf of Mexico. Perfect for casual meals, sunset cocktails, and soaking up Old Florida charm.

The Waterfront Restaurant

The Waterfront Restaurant offers a blend of fresh seafood and upscale dining with stunning views. Its welcoming atmosphere and diverse menu make it a perfect spot for both casual and special occasions.

Compass Hotel Anna Maria Sound by Margaritaville

Compass Hotel Anna Maria Sound offers a vibrant dining experience with Floridays Woodfire Grill & Bar, serving fresh seafood in a casual waterfront setting, and Compass Bar & Chill, featuring signature Margaritaville drinks. The hotel's tropical ambiance complements its delicious cuisine.

Rod and Reel Pier

Rod and Reel Pier offers a charming, laid-back dining experience perched over Tampa Bay, serving fresh seafood and casual fare with stunning water views and a glimpse of local fishing life. Its cozy atmosphere and historic pier setting make it a beloved spot on Anna Maria Island.

Ginny's & Jane E's Cafe and Gift Store

Ginny's & Jane E's Cafe offers a blend of delicious breakfast and lunch options, complemented by a unique gift store filled with local art and quirky souvenirs. This charming spot embodies the warm hospitality of "Old Florida" in a historic setting.

Skinny's Place inc.

Skinny's Place is a classic beachside eatery offering juicy burgers and crispy fries in a casual, Old Florida setting. It's a rustic spot perfect for a laid-back meal near the beach.

The Porch Restaurant Anna Maria

The Porch Restaurant offers a sophisticated dining experience with top-quality steak, fresh fish, and seasonal entrées, set within a historic home on Anna Maria Island. Its intimate ambiance and extensive wine selection make it a sought-after destination for special occasions.

Hurricane Hanks

Hurricane Hanks offers a casual, island-style dining experience with a focus on fresh seafood and classic American fare. The restaurant provides a laid-back atmosphere perfect for enjoying great food and drinks in the heart of Holmes Beach.

Attractions

Ana Maria island

Explore Anna Maria Island's serene beaches and tranquil waters, perfect for swimming and water activities. Nature lovers and families will enjoy the island's peaceful atmosphere and diverse wildlife.

Manatee Public Beach

Manatee Public Beach offers a serene escape with pristine white sand, calm Gulf waters, and activities like swimming and paddleboarding. It's perfect for families and those seeking relaxation and recreation in a beautiful coastal setting.

Holmes Beach

Experience the serene beauty of Holmes Beach, where you can relax on sandy shores, enjoy water sports, and soak up the Florida sun. It's perfect for families and beach lovers seeking a tranquil getaway.

Anna Maria Island Beach

Anna Maria Island Beach offers serene white sands and clear, warm Gulf waters perfect for swimming, shelling, and dolphin watching, making it ideal for families, nature lovers, and anyone seeking a peaceful beach escape. Its tranquil vibe and stunning sunsets create unforgettable moments.

Robinson Preserve

Explore Robinson Preserve, a 600-acre haven offering hiking, kayaking, and bird-watching amidst mangroves and scenic waterways. Nature lovers and outdoor enthusiasts will delight in its diverse ecosystems and panoramic views.

Fort De Soto Dog Park / Beach

Fort De Soto Dog Park and Beach offers a unique experience for pet owners, allowing dogs to play and swim freely in a designated beach area. It's perfect for those seeking a fun, social outing with their furry friends.

De Soto National Memorial

De Soto National Memorial offers a blend of history and nature, perfect for those who enjoy hiking, kayaking, and exploring historical sites. It's ideal for families and nature enthusiasts seeking a mix of adventure and educational experiences.

Bean Point Beach Access

Bean Point Beach is a secluded gem on Anna Maria Island, offering serene views and tranquil waters perfect for those seeking a peaceful escape. Locals and nature lovers alike enjoy its stunning sunsets and pristine sand.

Palma Sola Botanical Park

Palma Sola Botanical Park offers a peaceful stroll through lush gardens featuring rare tropical fruits, vibrant butterfly habitats, and themed plant collections—perfect for nature lovers, families, and anyone seeking a serene outdoor escape.

Fort De Soto Park Batteries And Military Post

Explore historic Fort De Soto Park, featuring the last four surviving 12-inch seacoast mortars in the continental U.S. and offering a glimpse into military history and stunning Gulf views. This site is perfect for history buffs and nature lovers alike.

Beach N Rides

A trusted local provider to ensure you have easy access to high-quality golf cart rentals during your stay. You may contact Beach N Rides at 941-251-7916. Use the discount code: Serendipity at checkout to receive your special rate.

Coconut Rentals

A trusted local provider to ensure you have easy access to high-quality golf cart rentals during your stay. You may contact Coconut Rentals at 941-269-1080. Use the discount code: Serendipity at checkout to receive your special rate.

Things to know

Cancellation policy

50% refund up to 60 days before check-in. No refund after that.

Property rules

Pets allowed with fee

No smoking - fees will apply

Events allowed

Safety & security

Check-in after 4:00 pm

Check-out before 10:00 am

8 guests maximum

Availability & Pricing

DatePrice (USD, excl. fees and taxes)Availability
Aug 24, 2026$900Not Available
Aug 25, 2026$900Available
Aug 26, 2026$960Not Available
Aug 27, 2026$960Not Available
Aug 28, 2026$960Not Available
Aug 29, 2026$960Not Available
Aug 30, 2026$900Available
Aug 31, 2026$900Available
Sep 1, 2026$900Available
Sep 2, 2026$900Available
Sep 3, 2026$900Available
Sep 4, 2026$1184Not Available
Sep 5, 2026$1242Not Available
Sep 6, 2026$1239Not Available
Sep 7, 2026$900Available
Sep 8, 2026$900Available
Sep 9, 2026$900Available
Sep 10, 2026$1042Not Available
Sep 11, 2026$1110Not Available
Sep 12, 2026$1111Not Available
Sep 13, 2026$1018Not Available
Sep 14, 2026$976Not Available
Sep 15, 2026$1063Not Available
Sep 16, 2026$1074Not Available
Sep 17, 2026$1085Not Available
Sep 18, 2026$1175Not Available
Sep 19, 2026$1153Not Available
Sep 20, 2026$1074Not Available
Sep 21, 2026$1035Not Available
Sep 22, 2026$1007Not Available
Sep 23, 2026$965Not Available
Sep 24, 2026$1036Not Available
Sep 25, 2026$1144Not Available
Sep 26, 2026$1101Not Available
Sep 27, 2026$900Available
Sep 28, 2026$900Available
Sep 29, 2026$900Available
Sep 30, 2026$900Available
Oct 1, 2026$900Available
Oct 2, 2026$900Available
Oct 3, 2026$1140Not Available
Oct 4, 2026$1102Not Available
Oct 5, 2026$1146Not Available
Oct 6, 2026$1168Not Available
Oct 7, 2026$1125Not Available
Oct 8, 2026$1205Not Available
Oct 9, 2026$1385Not Available
Oct 10, 2026$1418Not Available
Oct 11, 2026$1406Not Available
Oct 12, 2026$1282Not Available
Oct 13, 2026$1282Not Available
Oct 14, 2026$1283Available
Oct 15, 2026$1289Not Available
Oct 16, 2026$1294Not Available
Oct 17, 2026$1248Not Available
Oct 18, 2026$1282Not Available
Oct 19, 2026$1282Not Available
Oct 20, 2026$1280Not Available
Oct 21, 2026$1250Not Available
Oct 22, 2026$1170Not Available
Oct 23, 2026$1106Available
Oct 24, 2026$1069Not Available
Oct 25, 2026$1020Not Available
Oct 26, 2026$978Not Available
Oct 27, 2026$960Not Available
Oct 28, 2026$965Not Available
Oct 29, 2026$1002Not Available
Oct 30, 2026$998Not Available
Oct 31, 2026$987Available
Nov 1, 2026$960Available
Nov 2, 2026$960Available
Nov 3, 2026$960Available
Nov 4, 2026$1191Available
Nov 5, 2026$1252Available
Nov 6, 2026$1256Available
Nov 7, 2026$1336Not Available
Nov 8, 2026$1034Not Available
Nov 9, 2026$981Not Available
Nov 10, 2026$1072Not Available
Nov 11, 2026$1091Available
Nov 12, 2026$1218Available
Nov 13, 2026$1223Available
Nov 14, 2026$1235Available
Nov 15, 2026$1143Available
Nov 16, 2026$1114Available
Nov 17, 2026$1100Available
Nov 18, 2026$984Available
Nov 19, 2026$1117Not Available
Nov 20, 2026$1402Not Available
Nov 21, 2026$1692Not Available
Nov 22, 2026$1765Not Available