[See all properties](http://www.expedia.ca/Hotel-Search?regionId=&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) Entire home # Beachfront Luxury +Heated Pool + Hot Tub +Golf Cart +Bikes+SUP Family-friendly vacation home on the beach, with water park ![Exterior](https://images.trvl-media.com/lodging/65000000/64650000/64646400/64646349/bca3ba24.jpg?impolicy=resizecrop&rw=598&ra=fit) ![4 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/65000000/64650000/64646400/64646349/addd0da3.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Smart TV, books](https://images.trvl-media.com/lodging/65000000/64650000/64646400/64646349/38aef161.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Interior](https://images.trvl-media.com/lodging/65000000/64650000/64646400/64646349/fb5ff39a.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Smart TV, books](https://images.trvl-media.com/lodging/65000000/64650000/64646400/64646349/3800ba33.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Amenities - Policies - Location Close to Anna Maria Beach and Bean Point Beach, Beachfront Luxury +Heated Pool + Hot Tub +Golf Cart +Bikes+SUP provides golfing on site, a water park, and a garden. Active travelers can enjoy kayaking, paddleboards, and bicycling at this vacation home. For some rest and relaxation, visit the hot tub. Stay connected with free in-room WiFi, and guests can find other amenities such as laundry facilities. 9.8 Exceptional ### Entire home 4 bedrooms4 bathroomsSleeps 82231 sq ft ## Popular amenities - Parking available - Dryer - Pet-friendly - Washer - Hot tub - Pool ## Add dates for prices Check-in Check-out Travellers ## About this property ### Entire place You'll have the entire home to yourself and will only share it with other guests in your party. ### Beachfront Luxury +Heated Pool + Hot Tub +Golf Cart +Bikes+SUP Tripletail @ 308 S Bay Blvd – Private Beachfront Luxury Home 4 King Bedrooms | 4 Bathrooms | Heated Pool + Hot Tub | Golf Cart Included Welcome to Tripletail, your private beachfront escape on Anna Maria Island. Perfectly located just one block from Pine Avenue and the historic City Pier, this luxury home combines stunning Gulf views with walkable access to shops, dining, and local attractions. From your back deck, watch dolphins and manatees swim by, or take the bikes and complimentary golf cart to explore the island at your own pace. ⸻ Home Highlights • Beachfront Location – Step directly onto the sand from your backyard. • Heated Pool & Hot Tub – Relax after a day in the sun. • Spacious Layout – Perfect for families and groups, with an open floor plan. • Gulf Views – Panoramic water views from multiple rooms and decks. • Golf Cart Included – Easy island transportation. \_\_\_\_\_\_\_\_\_ Layout Ground Floor • Beachfront King Bedroom with en-suite bathroom • Second King Bedroom with bathroom access • Open-concept kitchen, dining, and living room overlooking the Gulf Upstairs • Two additional King Bedrooms with private bathrooms • Comfortable sitting area for relaxing or reading ⸻ Why Guests Love Tripletail • Private beachfront home – no crowded condos or shared spaces • Short stroll to Pine Avenue boutiques, cafes, and restaurants • Watch breathtaking sunrises over Tampa Bay and walk to the pier for fishing or ice cream • Fully stocked kitchen for home-cooked meals • Luxurious touches throughout with plenty of space for everyone ⸻ This is more than a vacation rental – it’s your island sanctuary. Whether you’re relaxing by the heated pool, soaking in the hot tub, or enjoying cocktails on the deck as dolphins pass by, Tripletail offers the quintessential Anna Maria Island experience. ## Property amenities ### Beach - On the beach - Beach loungers - Beach towels ### Pool/Spa - Heated pool - Hot tub - Outdoor pool ### Internet - Available in the house: Free WiFi ### Parking and transportation - Car recommended - Parking on site ### Kitchen - Blender - Coffee grinder - Coffee/tea maker - Cookware, dishware, and utensils - Dishwasher - Electric kettle - Ice maker - Microwave - Oven - Paper towels - Refrigerator - Stovetop - Toaster ### Dining - Chef service - Dining table ### Bedrooms - 4 bedrooms - Bedsheets provided ### Bathroom - 4 private bathrooms - Bathtub or shower - Hair dryer - Shampoo - Shower - Soap - Toilet paper - Towels provided ### Living spaces - Dining table - Living room - Separate dining area ### Entertainment - Books - Games - Smart TV with cable/satellite channels ### Outdoor areas - Balcony - Barbecue grill - Garden - Outdoor furniture - Yard ### Laundry - Laundry facilities - Washing machine ### Work spaces - Desk - Desk chair ### Comfort - Air conditioning - Heating ### Pets - Pet friendly - Welcoming dogs only - 2 pets total ### Suitability/Accessibility - If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking. - Stair-free path to entrance - Tile flooring in public areas - Upper floors accessible by stairs only - Well-lit path to entrance - Smoking not allowed ### Services and conveniences - Change of bedsheets (on request) - Change of towels on request - Housekeeping (on request) - Iron/ironing board - Meal delivery service ### Location highlights - In a village - Near a health/beauty spa - Near a hospital - Near a zoo - Near an outlet shopping mall - Near the bay - Near the marina - Near the ocean - On the waterfront ### Things to do - Bicycles - Golf - Heated pool - Kayak - Paddleboard - Water park - Basketball nearby - Birdwatching nearby - Ecotours nearby - Fishing nearby - Golfing nearby - Hiking/biking trails nearby - Horseback riding nearby - Hunting nearby - Jet skiing nearby - Kayaking nearby - Motor boating nearby - Mountain biking nearby - Sailing nearby - Scuba diving nearby - Snorkeling nearby - Surfing/bodyboarding nearby - Swimming nearby - Theme park nearby - Water skiing nearby - Water tubing nearby - Wildlife walks nearby - Windsurfing nearby - Winery tours nearby ### Safety features - Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property) - Smoke detector (host has indicated there is a smoke detector on the property) - First aid kit - Fire extinguisher - Deadbolt lock ### General - At least 80% lighting from LEDs - Bed sheets changed on request - Bicycles - Double-glazed windows - Energy-saving switches in guestrooms - Garden - Housekeeping (on request) - Locally-owned and organized tours and activities - Recycling - Towels (changed on request) - Unit size: 2,231 square feet - Water-efficient showers - Water-efficient toilets ## Similar properties ![Exterior](https://images.trvl-media.com/lodging/35000000/34430000/34429000/34428938/e76acb16.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Serendipity Deux Beachfront Retreat Anna Maria - Pool - Hot tub - Kitchen - Washer 9.6 Exceptional 42 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-18&endDate=2025-10-19&selected=34428938&PinnedHotelID=34428938&HadPinnedHotel=true®ionId=-1&adults=2) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34330000/34329900/34329809/49e10ada.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Cloud 9 - BeachFront Splendor Anna Maria - Pool - Hot tub - Kitchen - Washer 10 Exceptional 43 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-18&endDate=2025-10-19&selected=34329809&PinnedHotelID=34329809&HadPinnedHotel=true®ionId=-1&adults=2) ![A heated pool](https://images.trvl-media.com/lodging/75000000/75000000/74999800/74999757/w2048h1364x0y1-99b3ba54.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Gulfview Estate: Beachfront luxury home with sweeping Gulf views Anna Maria - 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Pool - Kitchen - Washer - Dryer 9.8 Exceptional 17 reviews CA $998 CA $2,273 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-23&endDate=2025-10-24&selected=39205588&PinnedHotelID=39205588&HadPinnedHotel=true®ionId=-1&adults=2) ![Exterior](https://images.trvl-media.com/lodging/34000000/33510000/33500600/33500504/9db123c5.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### SEPT,-OCT. SPECIALS, BEACHFRONT, PRIVATE BEACH ON THE WATERFRONT, Bring your dog Anna Maria - Ocean view - Hot tub - Kitchen - Washer 9.6 Exceptional 186 reviews CA $375 CA $999 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-05&endDate=2025-10-06&selected=33500504&PinnedHotelID=33500504&HadPinnedHotel=true®ionId=-1&adults=2) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113450000/113441900/113441847/w2047h1364x1y1-e2bfe629.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Sea Haven:Family home steps to beach, pool, hot tub, Foosball, putting green! Anna Maria - Pool - Hot tub - Kitchen - Washer 10 Exceptional 6 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-18&endDate=2025-10-19&selected=113441847&PinnedHotelID=113441847&HadPinnedHotel=true®ionId=-1&adults=2) ![Terrace/patio](https://images.trvl-media.com/lodging/79000000/78700000/78699800/78699708/w1284h856x0y7-f5cf7233.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Beachfront Bliss – 4 King Bedrooms, Golf Cart & Shuffleboard Anna Maria - Hot tub - Kitchen - Washer - Dryer 9.4 Exceptional 28 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-18&endDate=2025-10-19&selected=78699708&PinnedHotelID=78699708&HadPinnedHotel=true®ionId=-1&adults=2) ![On the beach](https://images.trvl-media.com/lodging/33000000/32080000/32073900/32073855/w1690h1597x558y0-de1a7053.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Pet Friendly Bay-Canal Waterfront! Tiki Bar 5BR, 5BA Huge Pool, 2 Kayaks/Bikes Anna Maria - Ocean view - Pool - Kitchen - Washer 9.8 Exceptional 121 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-18&endDate=2025-10-19&selected=32073855&PinnedHotelID=32073855&HadPinnedHotel=true®ionId=-1&adults=2) ## Policies ### Check-in Check-in time starts at 4:00 PM Contactless check-in available Minimum check-in age: 25 ### Check-out Check-out before 10:00 AM Contactless check-out available ### Special check-in instructions You will receive an email from the host with check-in and check-out instructions ### Check-out instructions The host requires you complete the following before checking out: Load and start the dishwasher Gather used towels Remove personal items, remove leftover food and drinks, and take out the trash Turn off the lights and lock the doors Failure to complete these may result in a negative review from the host. ### Pets Pets allowed Service animals are welcome, and are exempt from fees Welcoming dogs only 2 total pets Note from host: Pre-Approval, signed waiver and pet fee required ### Children and extra beds Children are welcome ### Events No events allowed ### 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 This property accepts cash Onsite parties or group events are strictly prohibited Host has indicated there is a carbon monoxide detector on the property Host has indicated there is a smoke detector on the property Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation ### We should mention This property does not have elevators A car is recommended for transportation to and from this property ### Property is also known as Vrbo Property Tripletail Anna Maria Tripletail Private vacation home Tripletail Private vacation home Anna Maria 4 bed/4 bath beach front/ golf cart included 138874 ## About the area ![Map](https://maps.googleapis.com/maps/api/staticmap?&size=660x330&map_id=3b266eb50d2997c6&zoom=13&markers=icon:https%3A%2F%2Fa.travel-assets.com%2Ftravel-assets-manager%2Feg-maps%2Fproperty.png%7C27.53165%2C-82.72940&channel=expedia-HotelInformation&maptype=roadmap&scale=1&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=wtW2YFUcYWWAckmpqvY5ZSL6gmI=) Anna Maria, FL #### What's nearby - Anna Maria City Pier - 3 min walk - 0.3 km - Anna Maria Island Museum and Historical Park - 8 min walk - 0.7 km - Bean Point Beach - 20 min walk - 1.7 km - Anna Maria Beach - 20 min walk - 1.7 km - Bradenton Beach - 4 min drive - 2.1 km #### Getting around - Sarasota-Bradenton Intl. Airport (SRQ) - 47 min drive #### Restaurants - ‪The Sandbar Restaurant - ‬14 min walk - ‪The Ugly Grouper - ‬6 min drive - ‪The Waterfront Restaurant - ‬2 min walk - ‪Ginny's & Jane E's - ‬11 min walk - ‪North Shore Cafe - ‬11 min walk ## Frequently asked questions ### Does Beachfront Luxury +Heated Pool + Hot Tub +Golf Cart +Bikes+SUP have a pool? > Yes, this property has an outdoor pool. Pool types include heated pools. ### Is Beachfront Luxury +Heated Pool + Hot Tub +Golf Cart +Bikes+SUP pet-friendly? > Yes, this property allows dogs (limit 2 total). ### What time is check-in at Beachfront Luxury +Heated Pool + Hot Tub +Golf Cart +Bikes+SUP? > Check-in begins at 4:00 PM. ### What time is check-out at Beachfront Luxury +Heated Pool + Hot Tub +Golf Cart +Bikes+SUP? > Check-out is at 10:00 AM. ### Where is Beachfront Luxury +Heated Pool + Hot Tub +Golf Cart +Bikes+SUP located? > Nestled on the beach, this Anna Maria vacation home is within 1 mi (2 km) of Bay Boulevard Beach, Anna Maria Beach, and Bean Point Beach. Anna Maria City Pier and Bayfront Park are also within 10 minutes. ## Have a question? Beta Get instant answers with AI powered search of property information and reviews. 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