Vacation rentals with breakfast in Sarasota County

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!

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.

Nottingham Beach Bungalow Near Siesta Key Beach

Book your Summer 2026 getaway - 30% off stays of 28+ nights. Pet-friendly Nottingham Beach Bungalow near the #1 rated - Siesta Key Beach, downtown, Trader Joe’s, restaurants & SRQ. Enjoy a remodeled bath, stocked kitchen, T-Mobile 5G Wi-Fi, smart-lock self check-in, beach gear, assigned parking for 2 cars, private front-yard dining table & umbrella w/ seating for 4, & a charcoal grill. The shared fenced backyard w/ fire pit & propane grill. Best for 2; sleeps up to 4 to 6 with sleeper sofas.

Tropical Paradise, close to beaches/shops

Very clean, light and bright, open concept, nice and comfortable, great for relaxing or entertaining. Located on a beautiful tranquil lot, private, with a park like setting on a water front. Close to everything! Siesta Key Beach, Crescent Beach, Turtle Beach, Point of Rocks, mineral springs. Shopping, restaurants, tiki bars, boating, fishing, kayaking, trail riding and much more all nearby. Walk, bike-ride, rent the garage kept golf cart or jump in the car and be everywhere in minutes.

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

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.

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!

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.