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Exotic Escape home! w/ Heated Pool & Luxurious Spa

Discover a relaxing tropical escape on Florida’s beautiful Gulf Coast! Perfectly located on the border of North Port and Port Charlotte, you’ll be just minutes from shopping, restaurants, stunning Gulf beaches, fishing, golf, dinner theaters, parks, and countless local attractions. Whether you’re traveling with family, friends, or simply looking for a relaxing getaway, this is the perfect place to create lasting memories. So look no further, we have your perfect Florida getaway waiting for you!

Beautiful lakeview 2 bedroom 2 bathroom condo

Welcome to a private oasis with wi-fi connectivity while embracing nature Relax in the air conditioned Lanai with lake views Only 3 miles to the world-famous Siesta Key Beach & sunset This 2nd fl 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 enjoy the fresh breeze! Check out various birds, turtles in their private sanctuary

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.

10 min to Beach+Free Boat Parking+Kid-Friendly

Gather your favorite people and escape to this unforgettable 4BR 3BA retreat designed for group getaways, bachelorette weekends, weddings, and once-in-a-lifetime celebrations. ✔ House – 4BRs – Sleeps 14 ✔ 2 Living Areas ✔ Massive Kitchen ✔ Backyard (BBQ, Fire Pit, Shower,...) ✔ Games ✔ High-Speed Wi-Fi ✔ Smart TVs ✔ Free Parking (4 cars) ✔ Pets & Events OK (with approval) With space for up to 14 guests across two floors this property offers the perfect mix of comfort, privacy, and wow factor.

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.

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.

Chic Siesta Retreat – Pool, Hot Tub & Water Views

Pink Pineapple Properties Presents – Siesta Key Sanctuary. A chic four-bedroom haven on Siesta Key featuring a private pool, soothing hot tub, and beautiful water views. Guests can enjoy relaxing by the water or fishing from the dock (bring your own poles). Just a short walk to Siesta Key Village and a quick drive to world-famous Siesta Key Beach, this retreat blends comfort and style for an unforgettable stay.

Vacation Paradise Close to Beach! After renovation

Totally remodeled fantastic vacation spot with a luxurious screened in private heated pool - this spacious house has all the amenities of home so you'll never want to leave! Just a quick 7-10 minute drive to the beautiful free public beach, 12 minutes to fun Siesta Village, and 20 minutes to St Armand's Circle with tons of shops and restaurants!