Holiday rentals in Longboat Key

Turquoise Gem 1st Floor

Private beach access! *Designer Renovation* Single level, 4 min walk to bright white quartz sand. Welcome to UPGRADED beach paradise featuring: NEW full Stainless-Steel kitchen, NEW cabinets and granite countertops. LUXURY bathroom with granite top vanity, oversized shower tile with glass Mosaic Inlay and full glass enclosure. 65 inch 4k Roku Smart TVs with Super Fast 1000 MbPs internet. Very Posh Bedroom, KING SIZE Memory Foam Hybrid Bed. Pull-out QUEEN Size Memory Foam Bed in the living room.

Beautiful Island Beach House

Beautiful Island Beach House with pool/hot tub and private beach access on Longboat Key. The large light-filled spacious home is close to everything that you want for a fun, yet relaxing beach vacation: restaurants, bars, shopping, nature walks, and sandy white private beaches. Due to island restrictions, a 28-day stay is the shortest rental period allowed. Please note that this property is not available for young children given the surrounding water. Ages over 6 are welcome with supervision.

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!

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.

Condo with a View 2: Beachfront!

This charming seaside condo is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in exclusive Longboat Key, Florida! Located on the second floor, overlooking the heated pool and ocean, this dreamy one-bedroom condo is optimal for sunset viewing from a private, screened lanai. Take a 30-second walk to the pool and onward to the secluded beach with loungers and sun umbrellas. Enjoy a relaxing vacation at our peaceful condo at Silver Sands Gulf Beach Resort!

Charming and Updated 1 Bedroom in Runaway Bay

Our charming 1 BR/ 1 Bath condo is a new to the rental market. It was formerly owner occupied. The property is in the Bradenton Beach area of Anna Maria Island. Beach is right across the street with deeded access. The pool is the largest heated pool on the island. Fitness center has newer equipment. There is a fishing pier which also works as a great way to enjoy beautiful views of the Anna Maria sound. Free trolley stop is right in front of the property. Washer/dryer in unit.

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 unit. This unit has been completely renovated. The best 1 bed/1 bath in Longboat Key for a great price. While the views from the balcony are breathtaking, the interior has been redone to bring the outdoors in. While the views from the balcony are breathtaking, the interior has been redone to bring the outdoors in.

Florida West Coast Get-Away

Enjoy Florida's beautiful West Coast in your own cozy, private apartment . One bedroom, living room, kitchenette with breakfast bar, attached bath with shower. Central air and heat. Free wi-fi. Private drive and gated entrance. Everything you will need is here just waiting for your arrival. You'll find this a beautiful place near everything you will need to enjoy your Florida vacation. Not available for guests with infants.

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.