Holiday rentals with beach access 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).

Walkability · View · Hospitality

Waterfront Coastal Retreat | Steps from LBK Beach

Welcome to paradise— your tropical escape awaits! Wake up to island serenity in our brand NEW STUDIO SUITE where you'll enjoy peaceful lagoon views from your private balcony. This gem, located in the coveted Longboat Key Resort Club, beautifully blends modern touches with coastal charm. Bask under the sun and enjoy private access to Longboat Key Beach and the heated resort pool which is just steps away. Perfectly positioned for relaxation, adventure, and exploring the best of Downtown Sarasota.

Beach · Walkability · Quiet

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.

Walkability · View · Backyard

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

Beach · Walkability · Wi-Fi

Beach Bliss: Discounted August & September!

This sublime oceanfront studio condo is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in Longboat Key, Florida! On the ground floor, overlooking the heated pool and ocean, this dreamy studio 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...!

View · Walkability · Pool

New Modern on Beach Longboat Key (5 steps to Sand)

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!!!!

View · Beach · Pool

Gulf Front! Sunset Deck! + Walk to Bridge St Pier!

🌊🏄Welcome to The Surof House - where panoramic views of the Gulf of Mexico welcome you from almost every corner! 🏖️Experience the ultimate beachfront retreat at this unique & stunning property nestled across from one of the top beaches in the world. A perfect blend of luxury, comfort, & unparalleled views awaites. With an upstairs loft featuring 3 single beds & 2 downstairs rooms with king beds, it's an ideal getaway for families, friends, or anyone seeking a slice of paradise.

Walkability · Beach · Sleep quality

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.

Beach · View · Parking

Beach Condo with Quiet, Private Beach

Escape to our serene 2-BR beachfront condo on Longboat Key. This corner unit offers stunning Gulf of Mexico views and sleeps 6. Enjoy direct beach access, a heated pool, and a private patio perfect for sunsets. Located in the quiet Beach Castle Resort, it's the ideal beach vacation rental for families or couples seeking a tranquil getaway. Walk to local restaurants and cafes from your peaceful retreat. A guest-loved home, consistently rated top 5% among Airbnb’s homes.

Walkability · Beach · Checkout

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.

Beach · View · Indoor spaces

Bradenton Beach Sunsets 2, Anna Maria Island, FL

Fully furnished water view beach cottage located on beautiful Anna Maria Island directly across the street from white sand beach and Gulf of Mexico. 1 Bedroom 1 bath unit that sleeps 4 with the queen pull out couch. Beach chairs/umbrellas/Boogie boards/laundry room, etc. provided. Three blocks from historic Bridge Street with lively restaurants and bars. Free island trolley and across the bridge from Cortez fishing village. Free off-street parking.

Beach · View · Air conditioning

The Beach Condo #107 Beachfront Full View

Unit #107 has private beach access. Only a few steps to the beach will full gulf view. This end condo unit is quiet, ground floor . It is a small studio: new queen murphy bed and queen sofa bed. No separate bedroom. Limited initial limited supply of products/soaps/towels. Common use W/D across from unit. This is a small studio at 330 sq ft. It has been recently remodeled. Grounds, unit, pool recently renovated due to hurricanes.

Beach · Walkability · Family