Holiday rentals in Sarasota

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.

FlipFlopsOn III • ½ Mile Siesta Key • Walk to Bay

Experience life 4 blocks from the Gulf, ½ mile to Siesta Key — America’s #1 Beach. With effortless access to Sarasota’s dining & arts scene, Siesta’s white sand beaches, St. Armand’s, & Gulf Coast adventure! 2BR boutique bungalow • Sleeps 6 • 4 beds Situated in the coveted Coastal District (‘West of Trail’) — chef kitchen, beach gear, Smart TVs, marble spa bath, laundry, fast Wi-Fi. Grill lobster under stars, unwind in your tropical garden, & walk palm lanes to cafes, and waterfront sunsets.

Waterfront Siesta Key / Kayak to the Bay & Beaches

North end of Siesta Key. Entire place entry level . Waterfront king suite on Bayou Louise with private entrance & direct water access. One large parking spaces out front. An old town Malibu tandem Kayak is complementary for our guests ride to Sarasota Bay in minutes and reach Lido key, Bird Key, and Roberts Bay . Just 2 miles to North village, 2.6 miles to Siesta Beach. Freshly Remodeled ! Self check in keyless . remote work escapes, great relaxing for couple get away in the best of Sarasota!

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.

Sunny Palm Villa

Welcome to Sunny Palm Villa! This family friendly 3 bedroom 2 bathroom home with a heated pool is just the place you have been looking for. A wonderful place to unwind and relax by the pool or one of the nearby beaches. Conveniently located 20 minutes from Siesta Key Beach or Lido Key Beach. Only 15 minutes from University Town Center shopping, Mote Aquarium and Nathan Bendersen Rowing Park. The Legacy Bike Trail and famous Dutch, Amish restaurants in Pinecraft only 5 minutes away.

The Cottage (In the Country) Cozy, Quiet Retreat

Relax, unwind and unplug at this cozy Old Florida-style country cottage! Here you are away from it all in peaceful bliss... but if you want to go out for dinner, it's an easy drive into town! Located on a beautiful 5 acre plot, this guest home is the perfect spot for your Florida getaway! Just 30 minutes from Siesta Key and 6 minutes from the entrance to Myakka State Park, you can see the best of Florida, both the swamps and the beaches, all in one day!

Sarasota Bliss 2/2 Near Lido, Downtown, SRQ

Welcome to We Are Blissful Spacious 2/2 apartment just 3 blocks from the Ringling Museum, near Sarasota Airport, and minutes to Lido Beach, Siesta Key, and downtown Sarasota. Eclectically styled for comfort, it offers a full kitchen, open living area, and smart TVs for easy streaming. Rest well on memory-foam beds with organic linens, then enjoy the peaceful forest backdrop. Perfect for families, couples, or professionals visiting Sarasota.

Downtown Sarasota | Casa de Zara

Welcome to Casa de Zara! Immerse yourself in Sarasota history by staying in our quaint Adobe style home built in 1925 with a serene garden filled with plants and trees native to Florida. You will be 1 mile from Main St. and 4 miles to Lido Key. One block over you will find a fun filled park with tennis and pickle ball courts, a walking path and basketball courts. Less than a mile away is Bayfront Park which is perfect for watching sunsets!

Luxury 3/3 with Heated Pool, Spa, & Putting Green!

Experience luxury at this newly remodeled home with a brand-new pool, spa, and putting green. Centrally-located near downtown Sarasota, Siesta Key, Lido Key beaches, and St. Armand’s Circle, it features a full kitchen, 3 king bedrooms, 3 full bathrooms, outdoor dining, high speed internet, a 75” outdoor TV, fire pit, and EV charger. Pet-friendly with a fenced yard, pet crate, bowls & treats. License # VR24-00208

Heated saltwater pool near Siesta and Downtown

Escape to our brand-new, modern Sarasota home, perfect for families! Enjoy a private heated saltwater pool just steps from the master suite. Located minutes from the world-famous Siesta Key Beach and vibrant downtown Sarasota. This stylish oasis comfortably accommodates up to 10 guests, offering the ultimate Florida retreat with all-new furnishings and a fully equipped kitchen. Your private getaway awaits!

Magical Secluded Retreat

Light-filled mid-century gem, newly renovated with cathedral ceilings. A lush canopy of tropical plants and trees offers privacy and calm unusual for its central location in Sarasota's historic neighborhood on the Bay. Relax inside and out, and lose yourself in birdsong, gently swaying bamboo and beautiful nature. Just 10 minutes to world-renowned beaches and even closer to dining, shopping and museums.

Sarasota's Luxury Oasis

Stay in comfort and style at this centrally located home just minutes from Siesta Key, downtown, and Sarasota’s best restaurants. Enjoy your own private pool, spa, and thoughtfully designed interiors. Whether you're traveling as a couple, family, or group of friends, this is the perfect spot to relax, reconnect, and explore everything Sarasota has to offer. Walk to parks, local cafes, and more!