Vacation rentals with breakfast in Siesta Key

4.96 out of 5 average rating, 113 reviews

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.

Home in Bradenton

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

4.94 out of 5 average rating, 16 reviews

Home in Bradenton

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.

5 out of 5 average rating, 14 reviews

Iconic Retro Glam Stay • Firepit & Near Downtown

Step into Iconic, a glamorous vintage escape inspired by the legends who vacationed in Florida’s golden age. Enjoy bright retro décor, themed bedrooms, a record player, a sunny kitchen, and a lush outdoor lounge with dining, BBQ, and cozy fire pit. It’s a stylish, inviting getaway where Old Hollywood charm meets breezy tropical living. For your peace of mind, exterior security cameras monitor the driveway and entry 24/7. We respect your privacy; no recording devices are located inside the home.

5 out of 5 average rating, 13 reviews

A stunning sunset is captured over the ocean, with warm hues of orange and gold reflected on the water. Silhouetted palm fronds are visible in the foreground, and the roof of a nearby building is partially seen, adding depth to the coastal scene.

Home in Bradenton Beach

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!

A screened lanai features a round glass table surrounded by four black chairs. Lush greenery is visible through the screens, providing a tranquil view of the outdoor area. Soft lighting fixtures hang from the ceiling, enhancing the inviting atmosphere.

4.91 out of 5 average rating, 32 reviews

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.

4.93 out of 5 average rating, 160 reviews

A vibrant sunset is displayed across the sky, with hues of orange, pink, and purple blending seamlessly. Silhouettes of palm trees are seen in the foreground, framing the tranquil water below, which reflects the striking colors of the sky. Nearby structures are softly illuminated in the fading light.

Guest suite in Sarasota

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.

4.84 out of 5 average rating, 55 reviews

Condo in Sarasota

LJ's Cottages 4

BALCONY VIEWS - 2 bedroom, 2 bathroom second floor bungalow style unit with plenty of room for family and friends. Enjoy the Siesta Key sands and famous Point of Rocks beach access just steps away. Enjoy recently updated kitchen and large bathrooms. Our massive living room and dinning perfect for watching large 60in TV's with entertainment packages to relax after a long day at the beach. The properties amenities boast private balconies, tiki hut, pool, hot tub, grill, and parking.

Superhost

The two-story home is framed by lush greenery, showcasing a combination of wooden and stone exterior. A wrap-around deck is visible on the upper level, while the lower level features large windows and a paved pathway leading to the entrance.

4.7 out of 5 average rating, 43 reviews

Tropical Escape, Sarasota!

Discover Real Florida, UP CLOSE! Unique and tranquil. Enjoy nature & everything Sarasota! • Refreshing breezes: private wrap-around deck • Pets welcome* • Comfortable beds, Towels, Bedding • Fully equipped kitchen • Beach gear, Crib, Bikes • 1st day cont. breakfast • Boat/truck/RV* • Air conditioned, hot water • Special occasions* • EV Charging Station* • Secluded, yet close to Beaches, Parks, Shopping, Dining • Pool & fitness • Sleeps 1-12 • 1400 ft.² * Fees apply

A cozy living area features a plush blue sofa and two accent chairs. Light filters through large windows adorned with navy blue curtains. A sleek coffee table is positioned in front of a wall-mounted television displaying a scenic image. A ceiling fan adds to the relaxed atmosphere.

4.85 out of 5 average rating, 33 reviews

Nottingham Beach Bungalow Near Siesta Key Beach!

Book your stay for Summer 2026 now! 28+ day stays get 30% discount! This cozy Nottingham Beach Bungalow is in a central location with a large fenced-in shared yard, new Florida sunroom with vinyl windows & AC/outdoor-style living-room , and a backyard firepit for a relaxing evening, we are here to help you have an amazing experience on & off the beach! Situated in a quiet residential cul-de-sac, you are only a short drive to downtown, 10 min to Siesta Key beach.

4.92 out of 5 average rating, 60 reviews

A well-maintained outdoor area features a heated swimming pool surrounded by lush green grass. Lounge chairs with blue cushions are arranged around the pool, alongside wooden tables. Tropical plants provide natural privacy at the edge of the space.

Home in Anna Maria

Gulf Coast Paradise

Located at the North End of Anna Maria Island 3 blocks from the beach and 1 block from the bay. Brand new heated swimming pool. Three bedrooms, 2 baths with open living & dining floor plan. A large screened porch for ping pong and dining. Perfect for entertaining your friends and family. House is equipped with beach chairs, beach towels, boogie boards and toys for your day at the beach. Children supplies available upon request. Pak n Play, crib etc.

4.95 out of 5 average rating, 22 reviews

An outdoor kitchen area is showcased under a wooden structure with a peaked roof. Two blue lounge chairs are positioned by a sparkling pool, while a grill, bar stools, and a television are visible in the background, surrounded by lush tropical landscaping.

Home in Ellenton

Trophy Fish at the Oasis

Welcome to the "Trophy Fish," a private oasis where resort-style living meets relaxation and fun. Set on a lush half-acre, this retreat offers an in-ground pool and spa, fully equipped outdoor kitchen, putt-putt golf, cornhole, a fire pit, and a 85' TV with extendable arm for movie nights under the stars and views from the pool. Sonos speakers set the perfect soundtrack inside and out. 4 bedrooms, 3 full baths including the outdoor bathroom and shower.