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!

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.

Siesta Key Escape: Sleeps 10 - Pool - Gated Beach!

Unwind in this spacious 4BR/2BA Siesta Key getaway, set on a quiet street steps from gated, private beach entry. Enjoy a resort-style shared pool when you're not at the shore, then head out to Siesta Key Village restaurants, shops, and the island's top attractions. ✔ 4 Bedrooms (Sleeps 10) ✔ Private Beach Access ✔ Open Design Living ✔ Renovated Chef's Kitchen ✔ Private Patio & Shared Outdoors (Pool, BBQ, Games, Fire Pit, Lounges) ✔ Smart TVs ✔ Wi-Fi ✔ Laundry ✔ Parking Learn more below!

Sarasota Paradise/Stunning Home/Heated Pool

Bring the whole family. This home has lots of things for a fun vacation. Make great memories as you entertain in the lg kitchen, grab some coffee at the bar, sit on the patio and enjoy the beautiful view. Enjoy a walk or bike ride on the nearby Legacy Trail. Let this be a place where you experience the Blessings of God and be refreshed by His Grace as you spend time in our home away from your home. No pets! Beaches: - Siesta Key Beach, 7.7 mi. - Lido Key/St Armand’s Circle, 7.5 mi.

Modern, Bright Downtown SRQ A-Frame West of Trail

Enjoy this bright, newly renovated unique pool home on a street with mostly waterfront homes featuring 4 beds & 3 baths, office area options, loft reading nook, Bosch appliances, bedroom skylights, artful light fixtures and fully fenced with heated pool. Central to & minutes from Siesta Key, St. Armand's Circle/Lido Key, downtown. Walk to the Sarasota Arts Museum, grocery, Southside and downtown Restaurants & shops, Selby Botanical Gardens, Bayfront Park, & Marina Jack. VR24-00157

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. VR24-00265

Pool & Sand Volleyball | 3 Kings | 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.

Lux Pelican's Perch | Heated Pool + Hot Tub + Gym

BNB Breeze Presents: Pelican's Perch Welcome to Pelican's Perch, stunning Lux home. Located just a short drive from beautiful beaches and local attractions. Check out this fully loaded home. - Private Heated Pool - heated at NO extra cost from Nov 21 - April 1st - Built-in Hot Tub ​​​​​​​- Water filtration system - Beach Supplies - Luxe Modern New Construction - Garage Gym - Connected directly to the Legacy Trail with Bikes - Breville Espresso Machine w/ syrups

Minutes to Siesta! 4BR 2BT Heated Pool Fenced Yard

Spacious 4-bedroom, 2-bath home with a heated private pool, just minutes from the #1 Siesta Key Beach! Located in the Gulf Gate area, you’re only a short drive to the beach, grocery stores, and dining. Enjoy a fully fenced backyard, plenty of parking, and outdoor grill. Inside, you’ll find beach supplies, a fully equipped kitchen, Keurig & drip coffee makers, and TVs in every bedroom—everything you need for a comfortable and convenient stay 🌴☀️

Heated pool & Infrared Sauna, 2 min to beach

Our 3-story home offers privacy for multiple families and is just 1 mile from Siesta Key Beach. Call the free shuttle for a quick ride to the Village for shopping and dining. Enjoy TVs in every bedroom, a full kitchen, laundry room, infrared sauna, and beach chairs. Two bedrooms have private baths. Relax in the heated pool and covered outdoor dining area while watching the game, surrounded by palm trees and salty air. SunfishBeachSiesta awaits!

Beach Escape+Downtown | large yard/Heated pool

Welcome to our Tulum-inspired retreat, thoughtfully curated with every detail is crafted to bring you a true sense of escape. The laid-back luxury of natural textures & breezy open spaces designed for unwinding after a day of sun. Whether you’re sipping coffee on the patio or relaxing under the Gulf sunset, this retreat offers the perfect blend of comfort and serenity. Don't see your dates available? Message us! STR CERT #VR25-00124

Waterfront Home by Ralph Twitchell

Beautiful midcentury waterfront home on Phillipi Creek close to all that Sarasota has to offer. 5 miles to America's number 1 beach Siesta Key, and only a few short blocks from stores, nightlife, & other beaches. This quaint ​​getaway includes a kayak to enjoy the pure bliss of the calm ​​​​​waters of ​​Phillipi Creek as well as a game room including a pool table, foosball table, and a fireplace to lounge around and chat.​