Holiday rentals in Bradenton

Guest House with Hot tub & Heated Pool

Welcome to your serene retreat in sunny Florida! This beautifully finished 1-bedroom, 2-bathroom mother-in-law suite offers luxury, comfort, and privacy. With a heated pool and hot tub, we offer year round outdoor relaxation. Step into your own private oasis with a separate entrance and secluded patio, ideal for morning coffee or evening relaxation. Located in a quiet neighborhood backing up to a protected preserve, offering peace and natural beauty. Beach gear provided for easy beach days.

Vitamin Sea

Welcome to Vitamin Sea- a Luxe 3BR/2BA Escape in Lakewood Ranch! Centrally located and ALL BRAND NEW TOP TO BOTTOM & tucked into one of Lakewood Ranch’s most sought-after communities! From the moment you arrive, elegance surrounds you. Resort-style living! Community pool and cabanas, dog park across the street, as well as high-speed Wi-Fi, smart TVs, full-size washer/dryer, linai and garage for extra storage, Vitamin Sea is perfect for travelers, snowbirds, traveling nurses, & short term renters

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

River Cottage 2/2 - Kayaks & Huge Deck-Old Florida

Old Florida charm meets peaceful riverfront living at the Lazy Gator Lodge. This unique Braden River getaway features two spacious king en suite bedrooms, an open-concept living area, fully stocked kitchen, massive waterfront deck, & fenced yard perfect for pets. Guests can explore the river by kayak and paddle to local waterfront restaurants and live music spots. Centrally located near Lakewood Ranch, UTC, Bradenton and Sarasota — plus the white sand beaches of Siesta Key & Anna Maria Island.

The Florida Rooms

NEW POOL/SPA. Just 10 minutes from the beach, The Florida Rooms is a 3BR, 2BA retreat with NEW RESORT POOL & SPA, outdoor dining and living space, premium beds, rain showers, a full kitchen, and dining for 8. Extra sleeping includes a queen sofa bed and Pack ’n Play. Enjoy a pool table, ping-pong, board games, outdoor string lights, and a fire pit. We include beach gear—chairs, towels, umbrella, and wagon—for easy fun in the sun. Comfort, charm, and convenience await! Pool/spa heating included!

Speakeasy Bungalow: 2/1 Spa home walkable downtown

Welcome to Speakeasy Cottage – a standalone 2BR guesthouse adjacent to our main Green Gatsby property, offering privacy, charm, and relaxation. Enjoy your own private hot tub under a curtained pergola, a string-lit patio amid lush tropical plants, and a chic interior with modern boho decor. Perfect for couples or small families (queen + bunk beds). Walk to downtown Bradenton and the Riverwalk (ferry to Anna Maria Island), with gulf beaches 8 miles away. EV charger on site for your convenience.

West Bradenton Cottage *No Cleaning Fees or Chores

West Bradenton Cottage is clean, affordable, and great for singles or couples. 8 miles from Anna Maria Island, Holmes Beach, with Coquina Beach and Longboat Key just further down, 2-3 miles from downtown, Riverwalk, GT Bray Park, IMG Acadamy, less than a mile from the country club, 2 miles from Village of the Arts, and 9 miles from Sarasota Bradenton National Airport. Close to Manatee Memorial and HCA Hospitals. Cute, quaint, and cozy, with electric grill on porch, laundry, & fire pit.

Tipsy Flamingo | POOL • HOT TUB • FIRE PIT • GAMES

Dive into the curious home of Tipsy Flamingo. The tropical fever dream you didn’t know you needed! Stay in a historic home bursting with fluorescent colors, a pink-tastic Flamingo Suite, a wild Jungle Room, and a chill coastal Surf Den. Outside, swing under the pergola, battle it out in giant chess, soak in the hot tub, lounge by the fire pit, and float in the sparkling pool on your honorary pink flamingo throne. Pure fun, pure vibes, pure madness! 🦩

Casita Lantana, a 1925 cottage in a Tropical Oasis

Welcome to my original 1925 Casita, built in the heyday of the John Ringling era. We are centrally located between Sarasota, Lakewood Ranch, and Bradenton, making it an ideal place to explore all the area has to offer. Getting around is easy since we are located very close to the Ringling Museum of Art. Plus, it is only a short 15-minute drive to downtown Lido Beach and St. Armands Circle.

NEW! Heated Pool, Pickleball, Mini-Golf, Play Room

Welcome to The Current, a bold coastal retreat on a quiet dead end street in West Bradenton, 12 minutes to Anna Maria Island beaches. Sleeps 12 across 4 bedrooms (including a bunk room) with a heated pool and spa (included, no extra fees), private pickleball court, 4 hole putting green, 75" outdoor TV, 4 player arcade, fire pit, and giant lawn games. Just bring your bags and your crew.

10 min AMI | 15 min IMG | Heated Pool

Escape to paradise in this beautifully designed 2-bedroom, 2-bathroom bungalow, located in the heart of sunny Bradenton just 10 min to Anna Maria Island. This chic and tranquil retreat boasts modern comforts and coastal charm, offering the perfect getaway for relaxation and rejuvenation.

Coastal Cottage 1 - Close to the Beach - Updated

Kick back and relax in this peaceful, updated space. This bright and cheery home feels like a perfect retreat cottage! The location is only a 7-mile drive to the local beach! Everything inside the home is newly updated for your perfect Florida vacation!