Waterfront holiday rentals in Longboat Key

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in Longboat Key

Guests agree: these waterfront rentals are highly rated for location, cleanliness and more.

0 of 0 items showing

1 of 3 pages

Top guest favourite

Flat in Longboat Key

4.95 out of 5 average rating, 103 reviews

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).

Guest favourite

Apartment in Siesta Key

4.93 out of 5 average rating, 111 reviews

NO Stairs, beachfront & short 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.

Top guest favourite

Bungalow in Oldsmar

4.98 out of 5 average rating, 116 reviews

salt living at its best

- Resort Style Water front - Stand alone - Hot tub - Sunrise / sunset views on dock - free Kayaks - Internet / YouTube cable - 65” smart TV - Spacious Bedroom with king size bed, walk in closet and flat TV - Washer and Dryer in unit - Designated work space -Pet friendly - Fenced private patio - Free 2 cars / Boat Parking. - Central location ( beaches, restaurants, Tampa, St Pete’s, safety Harbor, Dunedin - 11 minutes from Ruth Eckerd event Hall - Pristine clean - Coffee station - Dining area

Guest favourite

Tiny home in Sarasota

4.89 out of 5 average rating, 221 reviews

@Tiffanythetinyhome| island | netflix|bike|hammock

You are about to book a famous HGTV 270ft² / 25m² tiny home on a private 1.5-acre island! ☆ Walk to dining, nightlife, and shopping ☆ Fully equipped kitchen (K-cup) ☆ Backyard fire pit + BBQ ☆ Screened-in outdoor lounge w/ hammocks ☆ 415Mbps ☆ Smart TV w/ Netflix ☆ Memory foam bed ☆ FREE Bikes + kayaks + beach gear 3 min → Siesta Key Beach 7 min → Downtown SRQ 12 min → Myakka River State Park (river kayaking + wildlife viewing) We use a compost toilet. Please read house rules for info.

Guest favourite

Apartment in Longboat Key

4.91 out of 5 average rating, 175 reviews

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 of Mexico 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.

Top guest favourite

Apartment in Longboat Key

4.99 out of 5 average rating, 137 reviews

Condo with a View 2!

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!

Top guest favourite

Apartment in Bradenton

4.98 out of 5 average rating, 121 reviews

KING Bed + AMI Beaches!

🎙️🦩Welcome to the Retro Flamingo! Your tropical getaway that combines style, fun, and the serene beauty of the Gulf Coast. This cozy, vibrant themed condo is the perfect destination for your next Beach vacation. Walking distance to Palma Sola Beach Causeway, where you can enjoy sun-bathing, horseback riding, jet skiing, and fishing! 5 mins or less from the Gulf of Mexico and powdery white sand beaches of Anna Maria Island! Kick back and relax in this retro “Old Florida” themed condo!

Guest favourite

Bungalow in Indian Shores

4.92 out of 5 average rating, 251 reviews

Beach Bungalow -Step in to the Sand! Indian Shores

If you are looking for a 5 star vacation this is your place! Floor to celing everything is brand new! Step on to the white sandy beach from our front porch. We have totally refreshed our private 2 Bed, 1 Bath, slice of paradise and it will melt your stress away. This Charming Bungalow is perfect for any vacation. Indian Shores is centrally located between St. Pete Beach and Clearwater Beach. Pinellas County is full of shops, restaurants, and activities. Book with us now!

Top guest favourite

Guest house in Bradenton Beach

5 out of 5 average rating, 168 reviews

Bradenton Beach Sunsets 1, 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.

Top guest favourite

Flat in Indian Shores

4.95 out of 5 average rating, 150 reviews

Beach Front Condo!

Escape to paradise in this stunning condo, situated right on the sand, you'll wake up each morning to the soothing sounds of the ocean waves and enjoy breathtaking views of the sparkling turquoise waters from your own private balcony. The condo is tastefully decorated in a modern coastal style, that will make you feel right at home. The spacious living area boasts plenty of natural light and comfortable seating for relaxing after a day at the beach.

Guest favourite

Apartment in Indian Rocks Beach

4.83 out of 5 average rating, 106 reviews

Ocean Front Beach Condo Gap Day Special 6/12-6/20!

Escape to paradise at this beachfront condo in Indian Rocks Beach! Enjoy breathtaking Gulf of Mexico views and stunning sunsets from your doorstep. Steps away from the beach, this condo offers unparalleled access to sun, sand, and sea. Explore nearby restaurants and bars, or simply relax and soak in the natural beauty. Perfect for a romantic getaway or a family vacation. Beach gear including towels, chairs and umbrellas is included!

Top guest favourite

Apartment in Indian Shores

4.99 out of 5 average rating, 111 reviews

Oceanfront living on Indian Shores Beach

Oceanfront condo right on the beach! Newly renovated with designer appointed accommodations. This beach front property makes you feel like you are staying in a 5 star hotel. PLEASE READ BEFORE BOOKING: This property will accomodate 4 adults. However, there is a blow up mattress for an additional two guests that can be used in the bedroom with the two twin beds. YOU MUST REQUEST 1 OR 2 MORE PEOPLE TO STAY BEFORE BOOKING!