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.
Practice yoga on a paddleboard and connect with nature in a tranquil setting.
Explore mangrove tunnels by kayak or paddleboard with experienced guides in Neal Preserve.
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.
See non-migratory dolphins and unique wildlife while exploring the bays of Manatee and Sarasota.
Experience a private dolphin tour and enjoy scenic views while learning about local wildlife.
Cruise to local sandbars and spot dolphins while learning about unique island wildlife.
Discover Jewfish Key and local sandbars on a private excursion with swimming and snorkeling opportunities.
Cruise Sarasota Bay with friends or family and enjoy flexible rental durations.
Experience dolphins, sandbars, and a relaxing sunset cruise in the bays of Anna Maria Island.
Discover Egmont Key’s history and wildlife on a relaxing boat cruise with snorkeling and shelling.
Relax in comfort with a private beach suite cabana for your group of six.
Relax with a customizable beach picnic suite, perfect for groups or couples seeking a unique outdoor meal.
Watch vibrant skies while riding gentle horses through shallow coastal waters at dusk.
Ride a gentle horse along the sand, then cool off with a unique swim in Palma Sola Bay.
Ride the latest 3-seater jet skis and enjoy hassle-free fun on the water.
Enjoy a self-guided paddle adventure with a versatile inflatable board.
Experience inshore sport fishing with an expert captain and a fully equipped boat.
Explore Lido Key’s mangrove tunnels with included gear and a map for a self-guided adventure.
Explore scenic waters with included gear, map, and lesson for a fun half-day adventure
Explore Longboat Key’s mangrove islands at your own pace with fully equipped half-day rentals
Paddle Sarasota's serene mangrove tunnels with a naturalist guide and spot birds, manatees, and dolphins.
Paddle crystal-clear bays to spot dolphins and manatees with expert naturalist guides
Paddle clear waters between Anna Maria Island and Longboat Key with a dedicated guide and flexible itinerary.
Cruise with up to 13 friends on a spacious pontoon equipped for sandbar hopping
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.
Paddle crystal-clear kayaks with LED lights to witness Shell Key’s sunset or glowing nighttime waters.
Experience marine life up close on a comfortable pontoon cruise for all ages.
Rent a pedal kayak and explore Sarasota Bay with all gear and safety equipment included.
Pedal effortlessly through Sarasota Bay and encounter vibrant marine life on a small-group guided adventure
Paddle a clear kayak to secluded mangrove islands and a sandbar for snorkeling, wildlife spotting, and relaxation
Enjoy a fun-filled fishing trip with all gear included and expert crew guidance.
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.
Discover Sarasota’s unique architectural styles on a guided 90-minute air-conditioned tour.
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
Explore Anna Maria Island with a street-legal golf cart rental for easy island travel.
Customize your paddle through mangroves, beaches, and birdlife with expert guides on a private 3-hour adventure.
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.