Holiday rentals with a fire pit near Anna Maria Island Beach

4.98 out of 5 average rating, 118 reviews

A bright and airy living area features large windows allowing natural light to fill the space. Comfortable seating is arranged around a woven coffee table, with art pieces adorning the walls. A door leads to outdoor views, enhancing the inviting atmosphere.

Home in Terra Ceia

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.

A spacious living area features a large sectional sofa, offering ample seating. A contemporary chandelier hangs from the ceiling, while a light-colored coffee table sits at the center. In the background, a modern kitchen is visible, accentuated by sleek cabinetry and bright lighting.

4.97 out of 5 average rating, 115 reviews

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

4.81 out of 5 average rating, 250 reviews

A winding stone path is bordered by lush greenery, leading through the expansive yard surrounded by tall trees. Various native plants are visible, creating a natural and serene environment.

Home in Anna Maria

Charming Beach house amongst huge Banyon Trees

Charming bright beach house on huge secluded tropical yard voted "A Tropical Paradise", on the quiet residential tip of Anna Maria island . Cozy Porchs and tropical fenced yard sits among grand Banyon Trees with native birds. 3 min's stroll over small fishing bridge to historic Pine Ave w/ quaint eateries /shops or Paddle board / kayak delivery to ami historic trail . 7 min’s walk to bay front beach and AMMA MARIA PIER, or to "Bean Point" voted 1 of the most beautiful beaches in the world.

4.86 out of 5 average rating, 139 reviews

Home in Longboat Key

Summer House longboat key

Luxurious waterfront home with bay and and canal view, new custom kitchen with a view to the pool and your own private tiki bar, dock that can accommodate up to 21 ft boat , whole house just received a complete inside and out make over. Tropical coconut palms, outside patio and grill. Fish on the dock and watch dolphins and manatee. Truly a tropical paradise just 7 minute Walk to your own private beach. minutes from St Armand’s circle. feel free to reach out with any questions or requests

Superhost

5 out of 5 average rating, 3 reviews

5BR, Sleeps 16, Htd Pool, Hot Tub, 5 min to IMG

Indulge in an unforgettable experience at Coastal Clubhouse, the perfect destination for your family or large group. Located just 5 minutes from IMG, this spacious 5-bedroom, 4-bath home sleeps 16 and is designed for fun and relaxation. The resort-style backyard boasts a heated pool, pickleball and basketball court, mini golf, fire pit, in ground trampoline, hot tub and pool side bar. Perfect for families with kids and teens, multi-generational groups, this home has something for everyone.

4.93 out of 5 average rating, 105 reviews

The exterior of a charming two-story beach house features a vibrant color scheme with light blue and white accents. Adjoining palm trees provide shade, while a spacious porch with outdoor seating offers a welcoming view of the surrounding yard. A sandy area leads to the driveway.

Home in Anna Maria

2nd House from the Beach with No Roads to Cross

Seaside Sanctuary is the upper level unit of a beachfront duplex. It is the 2nd house from the beach with no roads to cross. The front yard is thirty steps from one of the most pristine beaches on the Gulf of Mexico. The house is located on a quiet residential street near the north tip of the island. The front deck is a great place to watch the sunset. The house is clean, comfortable and well appointed. We welcome well behaved dogs and have a fully fenced yard for your pup to play.

5 out of 5 average rating, 10 reviews

Home in Largo

Lux Spa Retreat•Pool•Hot Tub•Sauna•10 min to Beach

You asked, we delivered. Inspired by our Top 1% listing and consistent 5⭐ stays at “The Tiny Oasis”, Haus De Noir is a moody, boutique 3BR/3BA retreat with Plunge Pool, Hot Tub, Sauna, Outdoor Cinema and More! Slip into the Midnight Kafana, your own after-hours Hideaway Bar with Karaoke, Lights, and Late-Night energy. Fully stocked with everything you need and then some! Family-Owned and Managed! We don’t just host we LOVE what we do! Just 10 mins to Indian Rocks & Madeira Beach🏝️.

4.98 out of 5 average rating, 109 reviews

Home in Sarasota

Pool, Shuffleboard, EV charg, Near beach, UTC mall

Welcome to Vistalodgings Villa Del Sol where families have fun ☀ 3 bedrooms: 1 king, 1 queen, 1 full, 1 twin bed and 2 full bathrooms ☀ Fully equipped kitchen: Keurig dual coffee maker, waffle maker, air fryer, electric kettle, blender, mixer, pots and pans ☀ Dining area for 8 ☀ Fast speed internet Wi-Fi ☀ Heated pool free of charge ☀ EV charger ☀ Shuffleboard, Pac-man arcade ☀ 5 Smart TVs with Disney Plus ☀ Bikes, beach chairs, umbrellas, cooler, beach toys ☀ Iron

The outdoor area features a spacious swimming pool surrounded by lush tropical plants and shaded by a screen enclosure. A hot tub is positioned beside the pool, and the bright blue water reflects the clear sky above.

4.91 out of 5 average rating, 115 reviews

Exquisite modern home with pool - 10 min to beach

A beautiful modern home 10 min to Anna Maria Island and the beach with breathtaking amenities in Bradenton Florida. This 3 bedrooms, 2 bathrooms property is appointed with exquisite finishes and furniture throughout, heating and cooling pool, hot tub, large patio with lounge chair, complimentary bicycles and beach chairs, sonos system, outdoor BBQ and much more. Additional Housekeeping can be provided at an extra cost. Please contact the Property Manager for more information.

4.98 out of 5 average rating, 109 reviews

Cottage in Bradenton

Cortez ~ Grouper Cottage. BRING YOUR BOAT!

This waterfront home with a private dock and boat slip is the perfect place to get away. Grouper Cottage is an ideal cozy place to unwind and enjoy sunsets and dolphins. You will fall in love with this refurbished historic cottage—set in a private, tranquil setting, with picturesque palm trees and mangroves surrounding the property's shoreline. Cortez dockside cottages is nestled on an acre with a compromise of old Florida with the historical background a laid back Island vibe.

4.97 out of 5 average rating, 36 reviews

Pool & Sand Volleyball | 3 Kings | Near AMI & IMG

Escape to Two Palms, a spacious 4-bedroom, 3-bath retreat in Bradenton, Florida. Perfectly located just minutes from the sugar-sand beaches of Anna Maria Island. Designed with comfort and relaxation in mind, this home offers everything you need for a memorable getaway. Step inside to an open-concept living space filled with natural light and plenty of space to unwind. Outside, enjoy a private salt-water pool and a beach sand backyard featuring a sand volleyball court.