Holiday rentals in Bird Key

Coolest Downtown Neighborhood - Ebikes, Beach Gear

Are you coming to Sarasota on vacation or perhaps considering moving here? If yes, then the Carriage House is the perfect place to use as a base camp while you explore the area and experience the best Sarasota has to offer. Quick and easy walk to dozens of casual restaurants, cool bars and unique shops. 5 minutes to Selby Gardens. 10 minutes to the Sarasota Bayfront. Main street is half a mile away. We provide tons of amenities including bikes, kayaks, beach chairs and umbrella.

Peaceful waterfront home

Take it easy at this unique and tranquil getaway. Nestled alongside a serene canal, our home is a sanctuary of tranquility and natural beauty. From the moment you step onto the property, you are met with charm and allure that only canal front residence can offer. For those who enjoy outdoor activities, the canal provides a perfect venue for kayaking, fishing and lounging in our cocktail pool and hot tub. Surrounding sliding glass doors opens up to 3 separate patios.

Beach, Village, Dock & Private Pool! One-of-a-kind

Fully Restored Post-Hurricane and Ready to Welcome You!! RCC in Siesta Key is a one-of-a-kind coastal cottage perfectly located between the beach, canal, and village. Enjoy a private heated pool, private dock, and one of the best locations on the island. This 1,500 square foot standalone bungalow has been fully restored with fresh post-hurricane updates. If you want a charming, private beach home with no shared walls and no condo feel, you have found the right place!

Family Getaway | 3BR Home Near Siesta Key Beach

Welcome to Banyan Tree Cottage! This 3BR/3BA retreat blends Old Florida charm with modern updates. Enjoy spacious living areas, a screened cabana-style lanai, and new appliances for comfort. Just over the North Siesta Key Bridge, you’re minutes from quartz-sand beaches, Southside Village, Downtown, and St. Armands Circle. Perfect for work, rest, or play—experience the best of Sarasota living. Book your stay today! City of Sarasota Registration Number: VR22-00013

Downtown Sarasota Canal-Front Luxury Home!

🦩 Exclusive Amenities Include • 3 Bedrooms, 2 Full Baths • 1 King Bed, 1 Queen Bed, and 2 Twin Beds (Sleeps 6) with Linens Provided • Free WiFi & HDTV’s • Private Screened Pool • Bayou Front with Dock • Regular Coffee Maker, Dishwasher, Washer & Dryer, and Kitchen Essentials Provided • Island Shuttle Transportation Available • Pet Friendly (Up to 25 lbs with an Additional Fee) • Free Driveway Parking for 3 cars • 10 Minute Walk (½ Mile) to Downtown Sarasota

Modern Escape with Pools Near Sarasota’s Best!

Furnished modern townhome with 2 bedrooms, each with private bath, full kitchen, Smart TV, washer/dryer, and screened lanai. Enjoy a peaceful, family-friendly community with 2 pools, sports courts, trails, lake, and dog park. Pet-friendly (maximum 1 pet up to 55 lbs or 2 small pets up to 20 lbs each). Minutes from Siesta Key, Lido Beach, The Ringling, and more. Safe, quiet, and highly rated,5-star guest reviews highlight comfort, location, and lifestyle.

Private Heated Pool Casita Near Downtown & Beaches

Built in 1925, Casita Verde blends classic vintage charm with modern comforts. This 2-bedroom, 1-bath home features a 55" flat-screen TV with HD cable and fast Wi-Fi. Relax by the private pool or enjoy peaceful evenings on the deck with your favorite drink. Pet-friendly and conveniently located near Downtown Sarasota on Bahia Vista, with an easy drive to Lido Key, world-famous Siesta Key, and I-75 for day trips and longer adventures. 🌴 Cert# VR24-00152

Beach N Bay 206 by Duncan Real Estate

Welcome to Beach N Bay 206! A honeymooners delight or a couple's retreat! Enjoy a romantic getaway! Don't miss your chance to stay at the North end of Anna Maria Island in the highly desirable village of Anna Maria, one of Coastal Living Magazine's Top 10 Happiest Seaside Towns! Located right in the middle of all that happiness, Beach N Bay is the island vacation cottage duplex that's so tropical and fun, you'll swear you can hear steel drums!

Clematis casita

Luxury awaits at this well appointed centrally-located property. Enjoy the screened in porch and the lush garden. Full kitchen including ice maker. The king sized bed is very comfortable with all cotton sheets and extra pillows. Walk to Southside Village for coffee, groceries or dining. Siesta key beach is just 3 and a half miles away. 5.3 miles to Sarasota international airport.

Tropical and Tranquil Bradenton Hideaway

This beautiful 2BR apartment affords a prime central location to both the Sarasota and Bradenton beaches. Spend a sun-soaked day by the Gulf, or simply unwind in your spacious backyard with an outdoor hammock, al fresco dining, and a grill for cookouts. EXTRA AMENITIES This pet-friendly home ($150 pet fee) includes complimentary Wi-Fi, beach chairs, and parking.

Rhodes Retreat - Beautiful Pool and Backyard Space

Bright and newly renovated home for a delightful family escape in Sarasota. Central location near beaches, shopping, and downtown, yet nestled in a serene neighborhood. Short walk to charming Amish Village of Pinecraft. Ample parking, garage, and spacious front yard. Option to book separate secondary unit. Siesta Beach 8.7mi, Lido 5.8mi. VR24-00264

2BR Penthouse - Stunning Beach Views on Siesta Key

The stunning vistas of The Jamaica Royale Penthouse welcome you to your dream condo located on the 8th floor, overlooking the magnificent Siesta Key Beach. This fully remodeled and elegantly furnished 2-bedroom, 2-bathroom condo is the perfect getaway for anyone looking to enjoy the beauty of the Gulf Coast.