Holiday rentals with outdoor seating near Caspersen Beach

Waterfront Escape on canal ocean access kayaks

This stylish waterfront home is perfect for group trips. This four bedroom two bath home has room for two families to fit comfortably. It has a variety of seating both indoor and outdoor to accommodate your stay. There is room to spend time together or find your own little quiet area. The home is located only minutes from the beach, pool, boat launch and fishing pier. Close to multiple waterfront restaurants and shopping. Only minutes from Sunseeker Resort, area boat tours and fishing charters

Gertrude's Siesta | Patio & 1-min to Beach/Village

The Village Studio Top location on island! Apartment with full kitchen, private patio, gated courtyard, in world famous Siesta Village! Leave the car behind and walk to white-sand beaches, 20 bars and restaurants, ice-cream, shopping, daiquiris, live music, craft beer, fresh oysters and seafood. Experience a combination of fun ease and relaxation you can't get in other vacations! Book a special getaway now! - Tollbooth by AirbnbCorpMiddlemen, but this property is from GertrudeRentalsSiesta

☀ Villa & Garden in Downtown ~ 5 Min to Beaches

Our coastal chic, contemporary Sun Villa is situated in Sarasota’s charming downtown historic neighborhood of Laurel Park. The villa's garden hideaway is a real Floridian oasis, complete with fire pit and sun loungers. Downtown and all its restaurants, bars and shops is just on your doorstep. Plus 3 sugar white beaches – including Siesta Beach one of the most beautiful beaches in the world – are only a 5-min ride away! We’ve poured our hearts & souls into this villa, it's our family business.

Siesta RV & Tent Resort (2 of 5 sites)

This natural, yet manicured 1/2-acre venue includes all the premium amenities of a 1st class camping/RV resort. As a private enclave, we excel in providing a more intimate, cleaner and exclusive camping experience only minutes from world-famous Siesta Key Beach. Our reviews say it all. Our tropical oasis also offers premium extras not found anywhere else, including: a large pool, portable a/c or heating units, a mini-frig, microwaves, coolers, beach accessories, bike rentals and many more.

The Bradford Cottage/Heated Pool /Mins to Siesta

If you are looking for a cozy retreat in a safe and private neighborhood than look no further! From the minute you step inside this immaculate private residence you will feel right at home. With a beautiful open floor plan with plenty of room to spread out, natural light that pours in every room and a spacious back porch overlooking the heated pool this is the perfect place to unwind and relax. Minutes from the #1 rated Siesta Key beach and downtown Sarasota you are in the middle of it all!

Sunshine Awaits- Heated Pool Home! 6 min to DWTN!

Escape to your own private Sarasota oasis! This 3-bed, 2-bath vacation home boasts a heated pool for sun-soaked days & unforgettable evenings under the stars. Find a fully-equipped kitchen, comfy living space, Smart TVs, & free WiFi. Included are a gas grill & board games for poolside BBQs & family fun. Close to local shops, restaurants, & parks. World-famous Siesta Key Beach & Lido Beach are a short 15 min away, along with a 10 min drive to vibrant downtown Sarasota & its cultural scene.

*Downtown home 10min. drive to beach; walk DT*

In the heart of Gillespie Park, this bright & spacious home is a 10 min. drive to Lido Beaches and within walking distance to downtown shops, grocery, farmer's market, opera house, restaurants, bars, live music, tennis, parks, antique shops and performing arts. Old Florida bungalow on the outside, inside, it's updated with new appliances and bathrooms. A banyan tree offers private, shady repose on the back deck w/grill and dining area. Message me for room availability.

Entire Rv with BBQ and Patio.

Escape to a charming and comfortable RV getaway, perfect for a relaxing retreat! This cozy RV is fully equipped with all the essentials, offering a unique stay with modern comforts. Step outside to enjoy your private patio, complete with a BBQ grill—ideal for outdoor cooking and unwinding under the stars. Located in a peaceful setting, this space is great for solo travelers, couples, or small families looking to experience the outdoors with a touch of home.

Coastal Cottage | Oasis w/ Fire Pit + Grill!

BNB Breeze Presents: Coastal Cottage! Vacation in a slice of paradise, just minutes away from the delightful Amish community of Pinecraft, and 20 minutes away from Siesta Key Beach! This incredible cottage includes: - Backyard Oasis w/ Fire Pit + Magical String Lights ​​​​​​​- Covered Back Porch w/ Egg Chairs! - Private Backyard w/ Grill - Outdoor Seating + Dining - Beautifully-Designed Interior w/ Vaulted Ceilings - Spacious Fully-Equipped Kitchen