Holiday 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

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 Piece Of Sunshine to Enjoy!

Beautiful two bedroom, two bathroom home on a dead end road completely fenced and gated it has a pull out couch, full kitchen, dining room, laundry room, and plenty of space to spread out. Located just 10 miles from Bradenton beach and minutes to Anna Marie island from there. 15 miles to Siesta Key Beach. Sarasota airport is 5 miles away, and Tampa Airport is 47 miles away. There are plenty of places to dine out and plenty of places to visit locally. Ideal space for enjoying time with family.

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.

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

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

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.

83rd St Villas West by Duncan Real Estate

Welcome to 83rd St Villas West! A stunning ground-level vacation villa just a 6-minute walk from the beach! With two bedrooms and two bathrooms, this rental sleeps up to six guests. You and your guests can sit back, relax, watch movies, and connect over effortless conversations in the living area. Top of the range, fully equipped kitchen with Cafe appliances, ample counter space, cook top and oven, extra-large fridge/freezer making meal prep a breeze.

Nottingham Beach Bungalow Near Siesta Key Beach!

Book your stay for Spring 2026 now! 28+ day stays get 30% discount! This cozy Nottingham Beach Bungalow is in a central location with a large fenced-in yard, new 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.

Historic Beasley House with Heated Pool

Welcome to the historic Beasley House, a charming 1926 Mediterranean Revival estate. - 4 bedrooms with 1 king bed and 3 queen beds - Heated courtyard pool and multiple terraces - Fully equipped kitchen and cozy living area - Wi-Fi throughout the property - Antique fixtures and original plank wood floors - Free parking, beach chairs, and cooler included - Located near Siesta Key Beach and top attractions

Perfect Location! Steps to Beach~Heated Pool!

Experience coastal luxury at Villa #2 Shrimp 🌴✨, a stylish studio just a 2-minute walk to Manatee Beach 🌊. Enjoy a king bed 👑, spa-like bath 🚿, kitchenette 🍽️, and a private tropical patio 🌿. Relax by the shared resort-style pool 💦, grill out 🍔, or explore nearby shops and dining 🚎🛍️. Dog friendly 🐾 with approval and includes 1 parking space 🚗—your perfect Anna Maria Island escape awaits!

[Kids Favourite] Epic Family Getaway Games Room |

🏖️ Your Dream Family Oasis — Minutes from Anna Maria Island! 🌴 Welcome to Epic Family Getaway, a West Bradenton retreat designed specifically for families who want to relax without the stress. Located less than 15 minutes from the world-famous white sands of Anna Maria Island, our home is more than just a place to stay—it’s where your family memories begin.