Mansion vacation rentals in Siesta Key

Modern Luxe On Legacy Trail | Pool + Rooftop Deck

✨ Welcome to The Legacy Oasis - where luxury meets adventure! This brand-new 4BR/3BA modern home sits directly on the Legacy Trail (Add On E Bikes Available) Step through the backyard gate and you’re on one of Florida’s most scenic bike paths 5 minutes from Downtown - or 15 minutes to Siesta Key Beach. Spend the day by the pool, rocking on the swing beneath a majestic oak, and end the night on the rooftop deck with unforgettable sunsets. Sleeps 10 comfortably - perfect for families and groups!

The Bahia. Wellness House heated pool, spa, sauna

One-of-a-kind Sarasota wellness house retreat! This 4BR/2.5BA toxin-free home is minutes from Downtown, Lido Beach & Siesta Key, steps from the Legacy Trail, and near Pinecraft. Enjoy organic cotton & bamboo linens, toxin-free kitchen cookware and utensils and complete house RO system. Relax in private wellness garage w/ gym, infrared sauna & cold plunge- unwind by the brand-new pool & spa. Upstairs themed bedrooms and a music lounge with vinyl & karaoke—perfect for a complete family experience.

The Palm Court Villa

Architectural Elegance & Seamless Design From the moment you enter, soaring ceilings and clean architectural lines create an immediate sense of openness and light. The home’s open-concept design flows effortlessly into the chef’s kitchen and grand living space thoughtfully curated for elegant entertaining and relaxed luxury. 26-VR-000049 -Quartz waterfall countertops -Custom designer cabinetry -Premium, top-tier appliances -Expansive island gathering space -Integrated smart TVs & high-speed

Modern 4BR Home *Heated Pool & Spa*

Discover elegance in this centrally located Sarasota gem, featuring four bedrooms and two bathrooms to accommodate up to eight guests. Enjoy a laid-back vibe while lounging at Sarasota's beaches or immersing yourself in local attractions. Siesta Beach and Lido Beach are within easy reach at 7.6 and 6.4 miles respectively. Rest easy knowing commitment to cleanliness aligns with your travel priorities. Your serene vacation awaits in this beautifully adorned home. *Brand new pool* VR24-00265

Private Heated Pool Retreat for Two Families

🌴 Welcome to your private Sarasota escape - designed for easy, extended stays, where two families can relax together around a private heated pool. With generous living spaces and thoughtful touches throughout, the home balances comfort and connection. Located minutes from Siesta Key, Lido Beach, and downtown Sarasota, and within walking distance of a park with playground, public pool, courts, fitness areas, and scenic trails. Relaxed, comfortable, and ideal for memorable family getaways.

Luxury Villa with Pool, Game Room, Near Beach

Welcome to your tropical luxury escape! Spacious living flows to the heated pool, game room and sunny patio—perfect for family fun. • Bedrooms: 4 private suites, plush linens to ensure restful nights. • Location: Quiet neighborhood just minutes from the sandy beach, dining and shopping hotspots. • Heated pool & sun loungers • Arcade-style game room • Fast Wi-Fi & 5-star cleanliness • Pet friendly with fenced yard Have questions? We reply in under an hour—book your stay today! VR24-00060

House of Agape | Modern Luxury Escape w/ Pool

BNB Breeze Presents: House of Agape! A modern Sarasota retreat crafted for Pure Luxury. Designed with love, this golden oasis offers a private pool, sleek contemporary décor, a premium Jura coffee bar, and a fully equipped garage gym. Top amenities elevate this beautiful property even more: • Private Saltwater Heated Pool - heated at NO extra cost from Nov 21 - April 1st. • Modern Luxury Space • Professionally Designed and Furnished • Gym Set Up • Outdoor Dining Space • Beach Supplies

Beautiful Home Steps to Gulf w/ Pool, Spa & Views

Wake up to coastal luxury at Just Lanai-ing Around, a stunning retreat just steps from the Gulf. Start your mornings with ocean breezes, spend afternoons by the heated pool and spa, and end the day on the two-story rooftop deck under glowing skies. Designed for effortless comfort, the home offers spacious living areas, serene king suites, playful spaces for kids, and walkable access to the beach and St. Armands Circle. Your elevated Lido Key escape is ready to be enjoyed.

The Siesta Key Retreat - An Island Garden Oasis!

Your family will be close to everything when you stay at this centrally-located place on Siesta Key while still enjoying the private garden oasis this home has to offer. Just steps from the quaint shell beach or a bike ride to the beautiful sand of Siesta Key beach to spend the day or venture to the cool vibes of Siesta Key Village for dinner and shopping!. Additionally, you're only a few miles from the vibrant downtown Sarasota and St. Armand's Circle (26-VR-000095)

Sweet "Rae" of Sunshine

Welcome to Sweet "Rae" of Sunshine, a newly updated coastal oasis in the heart of Siesta Key! This family-friendly, spacious home is just a few blocks from Siesta Key Village and the #1 rated white sand beaches in the country! A quiet neighborhood providing a serene stay, yet extremely convenient location to all Siesta Key has to offer! 4 bedrooms, 2.5 baths. Sleeps 11 guests. Heated pool/spa with private Lanai. Plus, a 6-seater ELECTRIC GOLF CART INCLUDED IN YOUR STAY!

4 BR Pool Home | Sand Volleyball | 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.

Casa Bella-5BR/Waterfront/Pool/Spa-9 Min AMI

Beautifully renovated 5 bedroom home. Located 3 minutes from beach access and 9 minutes to Anna Maria Island. A massive waterfront patio with string lights and heated pool and spa encompass this house. Master bedroom with walk-out to spa. Custom double walk-in shower in master suite. Family room with 86" television, decorative fireplace, and 15' ceiling. Roku TV’s in every bedroom. Outdoor propane grill. Beach chairs, umbrella, and cart. We welcome you to Casa Bella.