Vacation rentals with a kayak near Bean Point 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

Hibernate in our Bear Creek Home

This 3 bedroom 2 bath home is located in beautiful Bear Creek. Don't worry, no bears! Great place to relax and enjoy the pool, in a quiet, safe neighborhood. Next to Pinellas Trail, a 40 mile paved trail. Great for walking, running and biking. You can bike downtown 6 mi or 4.6 miles to beaches. We have bikes and for those more adventuresome we have kayaks you may use. House features stable, high speed internet. Close to great restaurants, drugstores, supermarkets and coffee shops.

Sunshine Cottage: 30’ Pool & Dock, Steps to Beach

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.

Bay Breeze Cottages #3

Bay Breeze Cottages is an Old Florida Charm Boutique Resort located on historic Anna Maria Island. Bask in the endless sun all year long, take a swim in our private heated pool with your favorite beverage, or head out anywhere on the island in our street legal gas powered golf carts to any of the local restaurants, piers, sand white sand beaches, and all other attractions the island has to offer. Come enjoy your own slice of paradise at Bay Breeze Cottages on Anna Maria Island.

Sea Gem | Waterfront Oasis w/ Pool, Dock + Kayaks

BNB Breeze Presents: Sea Gem → Welcome to your private slice of paradise—a stunning waterfront retreat. Designed for unforgettable days under the Florida sun, this home blends comfort, style, and nature. - Private dock with string lights - Heated Saltwater Pool - heated at NO extra cost from Nov 21 - April 1st - Rooftop deck with sweeping views - Kayaks and paddleboards for adventures - Outdoor kitchen with grill and wine cooler - Peaceful dolphin sightings from your backyard

River House with Kayaks. Relax on the River.

Grab a kayak, and hop on the river for a chance to see some of Florida's wildlife. Birds, otters, and alligators! The Riverhouse is a one of a kind vacation home. A fully equipped kitchen, living Rm with leather couches and a dining area. 3 bdrms- a King in the Master, 2 twins in 2nd and a bunk rm, 2 full baths, a balcony, and 2 patios. Situated on a quiet cul-de-sac, only 5 mins from I-75 and 10 mins from UTC Mall, Benderson race park, and exceptional dining experiences.

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.

Waterfront Pool Home Steps to Beach

Escape to our waterfront oasis on Anna Maria Island! This bright, updated home features a private heated pool, hot tub, and dock. Perfect for families, it's just a 5-minute walk to the world-renowned Gulf beaches. Enjoy stunning sunrises, a dedicated workspace, and modern coastal decor. Explore the island with ease via the free trolley. Your perfect getaway awaits!

Casa Coquina: waterfront, pool, hot tub, boat lift

Beautiful Vibrant Community within driving distance to downtown St. Petersburg, FL. Enjoy what this oasis has to offer from the pool ( not heated ), hot tub, kayaks, sunrise overlooking the Tampa Bay, and it's quick drive to what St. Petersburg has to offer. This home is minutes away from vibrant downtown, the pier, great restaurants, and coffee.

Las Palmas Beach Rentals unit 2

Ground floor; limited beach view . Steps to the white sandy beach. Free parking to registered guest. Furnished rooms, full size kitchen, linens provided. Free trolley stop on the block. GREAT LOCATION! Shopping and restaurants short walking distance. Check out our guidebook for additional island tips. Once booked it will be in your itinerary.

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.