Discover amazing Holmes Beach activities and premium in-home experiences.
Holmes Beach is the heart of Anna Maria Island—a sun-dappled slice of coastal paradise where flip-flops are the daily uniform and the pace is set to island time. With sugar-soft sand, warm Gulf waters, and a friendly, easygoing vibe, this beach town is the perfect blend of relaxation and charm.
Customize a 3-hour beach picnic with setup and cleanup included
Enjoy a full-day beach suite for six with cabanas, chairs, towels, games, and a cooler—set up and cleaned up for you.
Soar up to 800 feet for a thrilling 10-minute parasail flight with an expert crew over the Gulf of Mexico
Soar up to 800 feet over the Gulf on a 10-minute flight during an easy 1.5-hour parasailing outing.
Cruise the Intracoastal with room for up to 12 and flexible 4–8 hour rentals
Discover Jewfish Key and local sandbars on a private excursion with swimming and snorkeling opportunities.
Experience dolphins, sandbars, and a relaxing sunset cruise in the bays of Anna Maria Island.
See non-migratory dolphins and unique wildlife while exploring the bays of Manatee and Sarasota.
Discover Egmont Key’s history and wildlife on a relaxing boat cruise with snorkeling and shelling.
Cruise to local sandbars and spot dolphins while learning about unique island wildlife.
Explore Anna Maria Island with a street-legal 6-seater and included delivery
Ride a gentle horse along the sand, then cool off with a unique swim in Palma Sola Bay.
Enjoy a self-guided paddle adventure with a versatile inflatable board.
Fish inshore waters with a US Coast Guard–licensed captain on a 2019 Sea Pro, tailored for all ages
Explore Longboat Key’s mangrove islands at your own pace with fully equipped half-day rentals
Paddle crystal-clear bays to spot dolphins and manatees with expert naturalist guides
Explore scenic waters with included gear, map, and lesson for a fun half-day adventure
Paddle Sarasota's serene mangrove tunnels with a naturalist guide and spot birds, manatees, and dolphins.
Explore Lido Key’s mangrove tunnels with included gear, map, and a brief lesson
Glide over shallow seagrass beds in a transparent kayak and spot marine life in Shell Key Preserve.
Paddle crystal-clear Tampa Bay waters in see-through kayaks to explore mangroves, beaches, and vibrant marine life.
Customize a private clear-kayak tour at Shell Key Preserve for all ages, up to 3 hours.
Paddle crystal-clear kayaks with LED lights to witness Shell Key’s sunset or glowing nighttime waters.
Enjoy a spacious 24’ deck boat with watersports allowed and seating for up to 12
Experience marine life up close on a comfortable pontoon cruise for all ages.
Pedal effortlessly through Sarasota Bay and encounter vibrant marine life on a small-group guided adventure
Paddle glass-bottom kayaks to a mangrove island and sandbar for swimming, snorkeling, and relaxing in St. Pete Beach
Fish 11–14 miles offshore with gear, bait, and license included
Experience custom deep sea fishing with comfort and flexibility on a private charter.
Savor Sarasota’s flavors and history in one unforgettable afternoon!
Explore Sarasota's historic neighborhoods and cultural landmarks on a 90-minute air-conditioned trolley ride.
Solve a circus-themed murder mystery on a rolling trolley with interactive fun and complimentary drinks.
Paddle through Jim Neville mangroves to a secluded beach accessible only by boat
Explore calm Turtle Beach waterways at your own pace with quality kayaks or paddleboards
Discover pristine beaches and vibrant marine life on a 4-hour cruise with snorkeling, shelling, and dolphin sightings
Cruise to pristine Shell Key, spot wild dolphins, and collect rare shells with an experienced local captain.
Search for shells and spot wild dolphins on a private cruise to Shell Key.
Witness a breathtaking Florida sunset from the water and spot playful dolphins along the way
Learn wing foiling fundamentals in a two-hour small group for all ages
Progress faster with private foil coaching for beginners to advanced riders
A custom chef‑curated feast celebrating bold local flavors and dietary wellness—served right in your home or rental
Stretch, unwind, and rejuvenate—right in the comfort of your vacation rental.
Life in Holmes Beach revolves around the shore. Mornings are best spent with your toes in the sand, watching shorebirds dart along the surf or catching a glimpse of dolphins just offshore. The beach here is wide and welcoming, with calm turquoise waters ideal for swimming, paddleboarding, or floating the day away. Grab a bike or golf cart and explore the quiet residential streets lined with pastel cottages and tropical blooms.
Central Holmes Beach is where the community comes together. Stop by small local boutiques, pick up a scoop of handmade ice cream, or enjoy casual island dining just steps from the sand. In the evenings, the sky turns peach and lavender over the Gulf—perfectly viewed from the public beach access at Manatee Beach, where live music and beachside bites add to the laid-back joy of it all.
Greetwell guests can book curated experiences like beach yoga, sunset cruises, or eco tours that explore the island’s wildlife-rich mangroves and waters.