Holiday rentals in Longboat Key

Longboat Key-OCEAN FRONT- on the beach

My place is located in a small boutique complex located on Longboat Key. Walk to shops, restaurants and park. You’ll love my place because of Gulf front location with full gulf view from living room, kitchen, master bedroom, and screened lanai. Completely updated in 2015 with full kitchen, two full baths and two bedrooms. A perfect place to relax, listen to the surf and watch amazing sunsets over the Gulf of Mexico. My place is good for couples, solo adventurers, and families (with kids).

Beachfront Escape – Private Balcony, Gulf 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.

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

Cozy private beach condo

Relax with the whole family at this peaceful place to stay steps away from the legendary longboat key private beach! Enjoy breakfast, lunch or dinner with the beautiful view of the Golf of Mexico right from your lanai. This lovely condo has 2 bedrooms 2 bath with small office and full equipped kitchen. The condo is located in a second floor accessible by stair and just a short walk to the complex 600 feet of white sand beach front, heated pool and bbq area. Minimum of 2 week rental available

Cedars Tennis -Gorgeous 2 bed, 3 level Townhouse

Kick back and relax in this calm, stylish space. In Cedars East, across from beach AND on the bay. Sleeps 6 - california king master & double bed upstairs. All new carpets upstairs and full laundry in the unit too! Lovely enclosed balcony overlooking trees and boardwalk. Couple of trek bikes available - 10 min walk/ 3 min cycle to beach. Large shared swimming pool, tiki bar, fitness center, tennis on site. Jetty, boardwalk & walk paths. Excellent location, pets allowed. RRR-00819. 2023

Sun-Kissed Memories!

This sublime oceanfront studio is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in Longboat Key, Florida! On the second floor, overlooking the heated pool and ocean, this dreamy studio condo is optimal for sunset viewing from a private lanai. Take a 30-second walk to the pool and secluded beach. Enjoy a relaxing vacation at our peaceful condo at The Beach at Longboat Key Resort! To see all four of our listings, click on my Host photo and scroll down...!

Turtle walk - Next to 5 top eats & Beach

Private BEACH Access! (Map in the photos)*Designer Renovation* Single level, 4 min walk to Bright White Quartz Sand, Welcome to UPGRADED BEACH PARADISE Featuring - NEW Full Kitchen, NEW Cabinets and Granite Countertops. LUXURY Bathroom with New Vanity, Oversized Shower Tile and Moen wand sprayer showerhead. 65 inch 4k Roku Smart TVs with Super Fast 1000 MbPs internet. Very Posh Bedroom, KING SIZE Memory Foam Hybrid Bed Complete with office Desk. FULL-Size pull-out bed in the living room.

New Modern Longboat Key*5 Steps to Sand*Heatd Pool

Newly renovated (November 2025) modern first floor condo literally five steps away from the sand walking outside from the lanai. One bedroom /One bath King bed in Primary Queen sleeper sofa in living room Key code entrance Free parking Heated Swimming pool on site Free Beach loungers on the beach Paid laundry machines on site Mid Island next to everything WiFi, cable, free parking Usually 7 night minimum Bring your toothbrush and bathing suite and prepare to unwind and relax!!!!

Beachfront Resort, Ocean View, Pool, Tennis, Gym

Beachfront on beautiful Longboat Key, this condominium offers all the amenities of a resort with the privacy and seclusion that has Silver Sands Beach Resort guests returning each year. Enjoy a coffee on your private patio looking at the Gulf and the beach. Relax on our private beach, walk on our soft white sand, take a dip in our heated beachside pool, or enjoy complimentary chaise lounges and beach umbrellas while breathing in the fresh air. You can't get closer to the beach.

Sunset and beach view from your balcony Unit 403

A luxurious experience on the beautiful beaches and emerald waters of the Gulf of Mexico awaits you when you check into this fabulous, fully renovated unit. It is one of the best one-bedroom, one-bath condos on Longboat Key, offering exceptional value. While the breathtaking views from the balcony capture the beauty of the Gulf, the interior has been thoughtfully redesigned to bring the outdoors in, creating a seamless blend of comfort and coastal elegance.

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.