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Lil John Coastal Cottage near Siesta Key Beach

Book your Summer 2026 Sarasota getaway-30% off stays of 28+ nights. Welcome to Robinhood's, pet-friendly Lil John Coastal Cottage is a cozy private guesthouse, located on a quiet cul-de-sac street near #1 ranked Siesta Key Beach, downtown, Trader Joe’s, restaurants & SRQ. Enjoy smart-lock self check-in, T-Mobile 5G Wi-Fi, coffee essentials, a comfortable bedroom, sleeper sofa, a screened in porch area, outdoor dining table & umbrella for 4, & shared outdoor spaces, a fire pit, in a fenced yard.

Palm Set– Sun Outdoors Resort~Pet Free Home

Palm Set - Resort Home | 2BR, 1.5BA, Sleeps 6 Golf Cart included - Pet Free Home Enjoy Florida resort living at Sun Outdoors Sarasota, one of the area’s most popular resort communities. This clean, well-kept home sleeps up to 6 guests with two private bedrooms and a sofa bed—perfect for families, couples, snowbirds, or longer stays. Designed for comfort and convenience, it’s an ideal home base for relaxing or entertaining , weekly activities for all age , $0 cleaning fee, golf cart included

Tropical Escape, Sarasota!

Discover Real Florida, UP CLOSE! Unique and tranquil. Enjoy nature & everything Sarasota! • Refreshing breezes: private wrap-around deck • Pets welcome* • Comfortable beds, Towels, Bedding • Fully equipped kitchen • Beach gear, Crib, Bikes • 1st day cont. breakfast • Boat/truck/RV* • Air conditioned, hot water • Special occasions* • EV Charging Station* • Secluded, yet close to Beaches, Parks, Shopping, Dining • Pool & fitness • Sleeps 1-12 (rates incl 2 guests*) • 1400 ft.² * Fees apply

65 ft Yacht Sarasota

Includes a 3-hour sunset cruise! Yacht has full kitchen, adjacent dinette, bar, living room, 4 TVs, wifi, A/C, massage table, guitars, bluetooth, and more. Vessel only needs 3ft of draft, which is great for traveling the Islands. Upper deck features 5 Captain swivel chairs, dinner seating for 6. Swim off the stern lower deck and climb back aboard from local beaches with an onboard ladder. Runs on Twin 670hp Cummins, and only burns 2 gallons per mile at 10 knots and will cruise at 25 knots.

Beautiful Home in Gulf Gate 4 Miles to Siesta Key!

Beautiful, totally remodeled Gulf Gate Home 4 Miles To Siesta Key Beach. This home has beautiful natural light in every room and has been fully updated with a modern touch. Includes so many wonderful sitting areas: modern living room, screened lanai with dining table, Florida sunroom with amazing farm table and lounge sofa, outside patio with grill and chaise lounges. Walking distance to Gulf Gate Library, Gulf Gate Restaurants and Nightlife. No RVs, Boat, or Jet Skis are permitted.

SIP & RELAX SPECTACULAR SUNSETS CLOSE TO SIESTA

Walk the No 1 beach in America, watch dolphins, wake up to sunny blue skies and the breeze from the bay. Watch spectacular sunsets daily whilst sipping your cocktail. Host your destination wedding - additional arrangements & cost. Located on the inter coastal waterway, a peaceful cul da sac & neighborhood close to Siesta Key. Gaze at the water & garden, spot the dolphins & birdlife. Close proximity to fabulous restaurants, boat/kayak rentals, Siesta Key, Downtown, & St Armands Circle.

Beautiful lakeview 2 bedroom 2 bathroom condo

Welcome to a private oasis with wi-fi connectivity Relax in the air conditioned Lanai with lake views Just 3 miles from the world-famous Siesta Key Beach & sunset This clean 2nd floor condo has ceramic tile floors throughout, open floor plan with large tv, master bedroom with king size bed and enclosed lanai with full view of the lake When the weather permits just open sliding doors on the lanai to enjoy the fresh breeze! Check out various birds, turtles in their private sanctuary

HOME HOME ON THE RANCH. SARASOTA FL.

My place is great for couples, solo adventurers, and business travelers. Who love the great outdoors and love nature at its best! Lots of wild life to enjoy including our horses, piggy Miss Daisy Mae, Chickens, and they will even share their organic eggs with you every morning 🐣All on our property. You are welcome to take photos to also share your awesome memories. Enjoy our fabulous sunsets!🌞walk our Canopy Roads, Myakka State Park, and The Crawling Museum. Entire home, Camper/RV

LJ's Cottage 2

STEPS TO THE SAND - Welcome to your tranquil oasis on Siesta Key at our first floor 2 bedroom, 2 bathroom beach bungalow style cottage unit with plenty of room for family and friends. Enjoy the Siesta Key sands and famous Point of Rocks beach access just steps away. Relax in our expansive living/dinning room while watching large 60in TV's, perfect after a long day at the beach. The properties amenities boast private balconies, tiki hut, pool, hot tub, grill, and parking.

Cozy Cottage, FirePit, BBQ, 5 Min Downtown

Savor the nostalgia at Yesterday’s Sunshine, a 2-bedroom escape blending vintage Florida charm with modern comfort. Spin classic vinyl on the record player or unwind in the spacious outdoor lounge, complete with a BBQ, fire pit, and games. It’s the perfect spot to slow down and embrace sunny, coastal living. For your peace of mind, exterior security cameras monitor the driveway and entry 24/7. We respect your privacy; no recording devices are located inside the home.

House With A Boat–Your Private Waterfront Resort

Imagine this: your own private house, your own private dock, and your own private boat — no marinas, no lines, no sharing. If you love boating, fishing, and floating in the pool while the kids chase lizards and cannonball into the water, House With A Boat is your dream escape. Perfect for the Captain and crew — yes, kids included.

Daze Inn Between: Resort 10 mins to Manasota Beach

Escape to a pet-friendly, 2-bedroom coastal home in South Venice! This peaceful sanctuary fits 4-5 guests. All pets are welcome! Please inquire for pet fee pricing. Perfect for a family vacation, remote work retreat, or romantic getaway just minutes from the beach. Enjoy the spectacular lagoon style pool, hot tub, and tiki bar.