Holiday rentals with a kayak near Anna Maria Island Beach

Private Island Old FL Waterfront Heaven on Earth

Discover the hidden secret of "Terra Ceia Island" (Heaven on Earth.) This 3 bed / 2 bath completely remodeled and charming A frame home offers breath taking sunrises from the bayfront private dock. Imagine enjoying your coffee in adirondack chairs while the sun rises over the Tilette Bayou. Enjoy bike rides through the old Florida country side (Bikes included). And rent a boat and cruise the pristine waterways around the keys. This home has everything you need for relaxation, peace, and fun.

AMI/IMG/Boat/Bikes/Golf/Hottub/Kayak/Beach/pool

Welcome to the Paradise Fun House, the ultimate spot for your dream bash! Our Airbnb oasis is packed with tons of fun and activities for an epic stay. Cruise around on free bikes or kayaks, fish with top-notch gear, challenge friends to mini-golf, chill in the hot tub, or enjoy our game collection. Golf clubs and beach gear are ready to roll. Our spacious layout is perfect for partying all night long. Book now for the ultimate fun or relaxing experience! Boat/Dog-sitting/cleaning are available

Near Anna Maria Island Beach-Studio on Wares Creek

This place delivers ample living space,latest amenities, and quick,easy access to Coastal Water,Anna Maria Island Beaches,and city Down Town. Spacious,bright,and tastefully furnished,with great screened porch,cozy gazebo,sparkling heated swimming pool . We supply 2 kayaks and everything that you might need to spend a day at the beach or on the water.We also supply fishing rods(adults and kids) and bait bucket. We can take you on a coastal trip in our boat if you wish (extra charges will apply )

1918 Historic Cottage • Walk/Bike to AMI Beaches

Wake up in a piece of Florida history — this cozy 1918 cottage is listed on the National Register of Historic Places. Stroll to nearby dockside seafood restaurants on Sarasota Bay, bike to AMI's sugar-sand beaches, or kayak through the mangroves in the peaceful nature preserve right across the street - kayaks, beach gear and bikes included. Authentic "Old Florida" charm — your one-of-a-kind Gulf Coast escape awaits. One of Florida's last working fishing villages — a truly rare find.

1/2 Block from Beach- Private Boat Dock & 30' Pool

o A beautifully renovated 3-bed 2-bath oasis designed for unforgettable family getaways, boating adventures, and pure relaxation. o While many rentals claim to be in Anna Maria, they are actually situated in the heavily congested Holmes Beach or Bradenton Beach areas. Nestled on the quiet, historic North End of Anna Maria City. Completely bypass the tourist traffic and long car lines, enjoying a peaceful, authentic neighborhood where everything you want is within a short stroll.

Pergola Oasis | Walk to Beach + Outdoor Living

Welcome to Salty Palm, a newly remodeled coastal retreat in the heart of Holmes Beach. Just a short walk to the white sandy beaches of Anna Maria Island, this home features a private covered pergola with outdoor lounge seating and dining, creating the perfect space to relax day or night. Steps from shops and eateries, with nearby bike and golf cart rentals, plus access to community amenities including a boat ramp, kayak launch, fishing dock, and tennis & pickleball courts.

Dolphin Cove Waterfront St. Pete Beach w/ Pool

THIS is the Florida life! A private oasis with a stunning tropical backyard and an oversized SALTWATER pool. Enjoy 140+ ft of waterfront on Bear Creek canal, where manatees and dolphins visit daily! Kayak just 15 minutes to nearby islands. Beaches are a quick 7-minute drive, downtown is 15 minutes away, and shops/restaurants are right across the street. The home is simple and unupdated, but the backyard is a true paradise you won’t forget!

Lux Mid-Century Downtown Courtyard+Parking

Private Mid-Century Palm Springs-inspired duplex in downtown St. Petersburg, just a short walk to everything! Featuring one-of-a-kind mid-century modern architecture, a spacious family room, luxurious king bedroom, full kitchen, laundry, and stylish bathroom. Private, fully fenced courtyard with secure parking. Relax in this safe, modern getaway with mid-century vibes and all the comforts of home!

AMI Sunset Beach - Gulf View Retreat w/ Pool+Decks

AMI's Sunset Beach part of 7 miles of white sand beaches! • 200+ five-star ratings over all sites! • Gulf-views inside home. • Decks with views of Beach + Gulf + Pool. • Heated Pool with sun shelf. • Paddleboard + Kayak + Firepit + Patio + Grill. • High-speed WiFi. • Top floor of duplex. • Central location next to Sunset Beach.

Tortuga Bay~Canal & Waterslide Putt Putt! TIKI HUT

Tortuga Bay is a canalfront 5BR/3BA escape just a 2-minute walk to the beach 🏖️! Enjoy a private pool with spa & waterslide 💦, tiki hut, BBQ, new putting green ⛳, private dock for a 30ft boat ⚓, and 2 kayaks 🛶. Walk to Pine Ave dining and shops, relax in stylish coastal interiors, and experience nonstop island fun! 🌞

Backyard Bliss Anna Maria Island

Welcome to Backyard Bliss, where resort-style living meets premier location! With the powdered sands of the Gulf of Mexico only 500 steps away and a retreat that offers endless amenities, a stay at Backyard Bliss will guarantee a smile on your face when you’re here, and a frown when you have to leave.

Boat Dock + Kayaks + Dolphins + Beaches + Hot tub!

✨Welcome to Retro Tides! 🌊 ✨A newly renovated waterfront retreat near Anna Maria Island Gulf Beaches! Observe Dolphins from your Private Dock! Relax in the Tiki Hut + Hot Tub! Take the Kayaks for a spin! This getaway is made for boating, fishing, beaching, and relaxing in true Florida style! 🌴