Holiday rentals in Longboat Key

Beautiful Panoramic Gulf and Sunset Views.

Beachfront Bliss — No Streets to Cross, Just Steps from the Sand! Enjoy breathtaking Gulf and sunset views from your private balcony in this spacious, newly updated condo. Featuring a brand-new bathroom and new flooring throughout, this 4th-floor unit (with elevator access) is the perfect retreat for your Longboat Key escape. The condo comfortably sleeps up to 6 guests. Sip your morning coffee or catch dolphin sightings and stunning sunsets from the balcony with 180° view of the Gulf. Elevator.

NO Stairs, Siesta beachfront. Walk to the village!

Welcome to your own private getaway directly on Siesta Beach! This ground floor unit is just steps from the powdery sands of Siesta Key. NO STAIRS Enjoy the updated bathroom with quartz countertops, new fixtures, paint, new furnishings, and décor. You literally walk out your door and directly onto the beautiful, fine, powdery white sand of Siesta Key Beach. Private Paradise directly on the white powdery sand of Siesta Key! 2 bedrooms 1.5 bathroom beachfront home with Gulf views that sleeps 6.

Beautiful Beach House

Beautiful, updated 1937 beach house. Original LongBeach cottage. Gated entrance to property. Three bedroom, two bath. Master bathroom has bathroom en suite. Hardwood floors throughout. Kitchen updated. Beautiful front and back porches to enjoy the sunshine. Private access to beach and Gulf of Mexico. Walking distance to shops and Tennis. Bedrooms include master with King, second bedroom with queen, third bedroom with two twins. Come join us in longboat key for sunshine, beaches,culture,tennis

Mid-Century Modern Beach Getaway

Heart of Southside Village 10 minutes from #1 beach in the USA, Siesta Key. Five-minute drive to downtown Sarasota, 10 minutes to St. Armand Circle, Lido & Longboat Key. Enjoy this peaceful space within walking distance to shopping, restaurants & groceries. Charming private guest house offers a queen bed, sitting chairs, table, dresser, large ensuite bathroom with a walk-in shower & private outdoor sunny space and patio. Use the grill to cook your next meal. It's the perfect couple's getaway!

Longboat Key Beach House

This quaint beach house with a private backyard and outdoor shower is everything you need to enjoy your relaxing Florida getaway and includes your beach supplies. A 3 minute walk to the beach and to the bay, this house is within a block of restaurants and a deli. Also Included is the use of a membership to Cedars East Tennis Club (5 minute walk), which has 10 HarTru Tennis Courts, a junior Olympic POOL, gym, bicycle rental and tiki bar. Only Minutes to Holmes, Bradenton and Coquina Beaches.

Gulfront Views! BEACHFRONT BARGAIN HUNT NOMINATED

THIS UNIT WAS NOMINATED TO BE FEATURED ON BEACHFRONT BARGAIN HUNT! Unit #102 Features: Full-size kitchen and Gulf-front views Bedding: 1 Queen Murphy Bed and a Sleeper Sofa Savor warm Gulf breezes while resting lavishly in this Gulf-front condo complex. Located directly on the beach, this resort features beautiful Gulf-front views. You are only steps from the white-sand beaches, placid turquoise waters and beautiful sunsets that will have you daydreaming about your next beach vacation.

Beautiful Beachfront Cottage on the Water

Renovated, romantic 1937 beach front cottage. Last of its kind in the quiet family setting of Indian Shores Florida, halfway between Clearwater Beach and Treasure Island/John's Pass. Truly an "Old Florida" experience with original pine floors, Florida room and covered porches, as well as updated kitchen and bathroom. This house, uniquely built near ground level, allows it to be waterfront on the beach while shaded by huge pine trees. You won't find a more tranquil setting on the beach.

Short walk to beach + Boat dock

The best of island living: a boat dock in back & deeded private access to the white sandy beaches of LBK, just steps down the street. Minutes from Coquina Beach, historic Bridge St. and Anna Maria Island. Sarasota, Lido Beach & St. Armands Circle are a short drive south. A well-stocked convenience store, deli and 3 restaurants (Continental, Italian and Mexican) are a block away; with Euphemia Hay, Lazy Lobster, Dry Dock, Chart House just a short drive.

Island property on Longboat Key by the Beach

Longboat Key Island Fun in a newly updated beautiful property! Newly updated 3 story townhouse on beautiful Longboat Key with two bedrooms and two and a half bath sleeps 5 guest comfortably on King, Queen and pullout single beds. This well equipped property is ready and stocked with beach chairs, a cooler, a beach umbrella, and pull buggy for your convenience. Two week minimum. and relax in this calm, stylish space.