Holiday rentals in Sarasota County

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.

Village Des Pins - 2 bedroom 2 bath villa

Village des Pins is a community of tranquil villas with lush greenery, ponds, wildlife, oversized heated pool, hot tub, tennis courts, clubhouse w/ pool table, & outdoor grilling area. This resort-like villa is located minutes away from Siesta Key beach, Lido beach, Venice beach, MOTE Marine Laboratory & Aquarium, Ringling museum, garden and theater, Big Cat Habitat, golf courses, fine dining & shopping. Nearby: Publix, Costco, Target, Sprouts, Detwiler farm market, Starbucks, Chick-fil-A, Pizza

Sarasota Tropical Place in the Heart of the Gulf!

Forget your worries in this spacious and serene space and enjoy all the magic Sarasota has to offer. This charming home is a 3 bedroom 2 bathroom with an open light living room. Kitchen fully stocked will meet all your cooking needs. Other amenities include TV, WIFI, and gas BBQ grill with patio Chaise Lounge Chairs. A fenced in patio with lush palms.This beautiful home is the perfect getaway for friends and families that is conveniently located in the heart of the Gulfs most beautiful beaches.

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!

Sarasota Florida -Wild Orchid Creek Cottage Home

Come enjoy old Florida living at this completely renovated cottage style home on nearly seven acres. Relax and unwind in this 1000 square foot private home with king bed and queen sleeper to accommodate up to four people. Open concept living, dining room and full kitchen. Laundry facilities available. Equipped with WiFi and direct tv. While enjoying the private backyard space, it is common to spot abundant wildlife and wildflowers. Wild orchids in many of the oak trees bloom in early summer.

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.

@Shellmateisland |tiny home| island| bikes| kayaks

⭑Octagonal 320ft² tiny home sitting on a private 1.5-acre island!⭑ ✯ Lake access ✯ Walk to dining, nightlife, and shopping ✯ Fully equipped + stocked kitchen ✯ Free bikes + kayaks +beach gear ✯ Backyard fire pit + BBQ ✯ Screened-in outdoor lounge w/ hammocks ✯ Smart TV w/ Netflix ✯ Memory foam bed ✯ 426Mbps wifi Ask which fruit trees are in season for a homegrown treat! 3 min → Siesta Key Beach 7 min → Downtown SRQ 12 min → Myakka River State Park (river kayaking + wildlife viewing)

Sandhill Sarasota

Welcome to your cozy Sarasota escape—designed for quiet moments, shared memories, and effortless comfort. This light-filled home features a warm, open layout with soft tones, inviting furnishings, and a calm, relaxed atmosphere perfect for couples or small families. Thoughtfully designed, family-friendly, and just minutes from beaches, dining, and local favorites—this is a place to slow down, reconnect, and feel at home. Find your quiet at Sandhill Sarasota 😊

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!

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!

Private Pool +Game Room Near Siesta Key | Sleeps 9

Experience your own private family resort near Siesta Key Beach. This spacious Sarasota vacation home sleeps 9 and features a private pool, game room, soccer field, playground, and outdoor BBQ lounge in a fully fenced backyard. Bright coastal interiors, a fully equipped kitchen, fast Wi-Fi, Smart TVs, free parking, and easy self check-in provide effortless comfort. Minutes from beaches, dining, shopping, and top Sarasota attractions.

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!