Vacation rentals with breakfast in Siesta Key

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

Blue Tide Bungalow

Relax & Play in Paradise – Family Retreat with Pool & Hot Tub and firepit in Bradenton, FL Welcome to your Bradenton getaway! Whether you’re here for the beaches, the ballfields, or simply a warm-weather escape, you’ll feel right at home the moment you arrive. This stylishly furnished 4-bedroom, 3-bath home comfortably sleeps 8–10 guests and offers everything you need for a relaxing and memorable stay. From coffee by the pool to sunset cocktails around the fire pit, no detail is overlooked.

BeachHouse:Sleeps 13:Ocean View:Spa:Rooftop Deck

☀️ This 4bdrm/4bath house is perfect for large groups or entertaining. Sleeps 14!!! 3 King beds and 2 bunkbeds (3 Twin, 1 Full), Trundle, & Pullout Sofa. Each room has its own private marble tile bathroom. Go upstairs to the Pool table room with built in bar. Then to the 3rd story Rooftop deck for sunbathing and sunsets. Backyard includes a firepit, 12 person swimspa, putting green, outdoor shower, grill, bikes, & beach amenity shed! Mere steps to the beach itself. Spacious & newly renovated!

Nottingham Beach Bungalow Near Siesta Key Beach

Book your Summer 2026 getaway - 30% off stays of 28+ nights. Pet-friendly Nottingham Beach Bungalow near the #1 rated - Siesta Key Beach, downtown, Trader Joe’s, restaurants & SRQ. Enjoy a remodeled bath, stocked kitchen, T-Mobile 5G Wi-Fi, smart-lock self check-in, beach gear, assigned parking for 2 cars, private front-yard dining table & umbrella w/ seating for 4, & a charcoal grill. The shared fenced backyard w/ fire pit & propane grill. Best for 2; sleeps up to 4 to 6 with sleeper sofas.

Beautiful Home in Gulf Gate 4 Miles to Siesta Key!

Beautiful, totally remodeled Gulf Gate Home 4 Miles To Siesta Key Beach. This home has beautiful natural light in every room and has been fully updated with a modern touch. Includes so many wonderful sitting areas: modern living room, screened lanai with dining table, Florida sunroom with amazing farm table and lounge sofa, outside patio with grill and chaise lounges. Walking distance to Gulf Gate Library, Gulf Gate Restaurants and Nightlife. No RVs, Boat, or Jet Skis are permitted.

SIP & RELAX SPECTACULAR SUNSETS CLOSE TO SIESTA

Walk the No 1 beach in America, watch dolphins, wake up to sunny blue skies and the breeze from the bay. Watch spectacular sunsets daily whilst sipping your cocktail. Host your destination wedding - additional arrangements & cost. Located on the inter coastal waterway, a peaceful cul da sac & neighborhood close to Siesta Key. Gaze at the water & garden, spot the dolphins & birdlife. Close proximity to fabulous restaurants, boat/kayak rentals, Siesta Key, Downtown, & St Armands Circle.

Beautiful lakeview 2 bedroom 2 bathroom condo

Welcome to a private oasis with wi-fi connectivity Relax in the air conditioned Lanai with lake views Just 3 miles from the world-famous Siesta Key Beach & sunset This clean 2nd floor condo has ceramic tile floors throughout, open floor plan with large tv, master bedroom with king size bed and enclosed lanai with full view of the lake When the weather permits just open sliding doors on the lanai to enjoy the fresh breeze! Check out various birds, turtles in their private sanctuary

LJ's Cottage 2

STEPS TO THE SAND - Welcome to your tranquil oasis on Siesta Key at our first floor 2 bedroom, 2 bathroom beach bungalow style cottage unit with plenty of room for family and friends. Enjoy the Siesta Key sands and famous Point of Rocks beach access just steps away. Relax in our expansive living/dinning room while watching large 60in TV's, perfect after a long day at the beach. The properties amenities boast private balconies, tiki hut, pool, hot tub, grill, and parking.

5BR, HtdPool, Pickleball, FootPool, 8 min to Beach

Golden days. Neon nights. Welcome to Electric Palms Bradenton. Just 10 minutes from Anna Maria Island's white sand beaches, this 5BR, 3BA private resort sleeps 19 and was built for unforgettable multi-generation getaways. Heated pool. Pickleball court. BattlePutt. Foot Pool. Glow gameroom. Giant Lite Brite. Lego Wall. Fire pit nights. Not just a stay, a backyard resort where kids light up, parents unwind, and every sunset turns electric.

Trophy Fish at the Oasis

Trophy Fish at the Oasis is where your group actually lives outside. Heated saltwater pool and spa, full outdoor kitchen, putting green, fire pit, cornhole, and a 75" smart TV under a covered pavilion. Sonos sets the soundtrack inside and out. The yard is professionally misted for mosquitos — you're genuinely comfortable in Florida. Four bedrooms sleep 10. 45 minutes to Anna Maria Island and Siesta Key and 25 min to St. Pete!

Sea La Vie by Duncan Real Estate

Welcome to Sea La Vie!This is the relaxing Island getaway that you have been looking for. You and the family will love staying in this beautiful three-bedroom, two-bath elevated home nestled in secluded surroundings, just one block north of Pine Avenue in the village of Anna Maria. Stroll to the Pier for tranquil bay views or have coffee at the Cafés and grab a bite at one of the eateries lining the historic shopping area.

Chic Siesta Retreat – Pool, Hot Tub & Water Views

Pink Pineapple Properties Presents – Siesta Key Sanctuary. A chic four-bedroom haven on Siesta Key featuring a private pool, soothing hot tub, and beautiful water views. Guests can enjoy relaxing by the water or fishing from the dock (bring your own poles). Just a short walk to Siesta Key Village and a quick drive to world-famous Siesta Key Beach, this retreat blends comfort and style for an unforgettable stay.