Apartment 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).

Family · Value · Parks

"Dream Away" at The Beach Dreams Resort

Dream-away is the top right unit with one bedroom, one bath, full kitchen, washer/dryer, dish washer and a balcony facing Gulf Drive. This unit has a wonderful beach front view. The balcony is not on the Gulf Side. If you are interested in renting beach chairs, umbrella and a golf cart, please let us know. Two chairs and one umbrella are 25/day. We will drop off and pick up. Golf Cart can be rented for the day or the week. One small to mid size car is allowed on premises. Ask about larger cars.

Value · Location · Backyard

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...!

Family · Location · Amenities

One Block to Beach - Ohana Hale Gulf View D 2 BR

Aloha and welcome to our island home. "Ohana" is Hawaiian for family & that is who you are when you stay w/ us. The 2 bedroom 1 bath suite is located on the second floor w/ a peek of views of the Gulf from the living room, 2nd bedroom & your outside deck. We also have a 3rd floor shared deck guests utilize to watch the sun sink into the earth over the Gulf of Mexico or enjoy soaking up the sun. You are 150 feet from stepping into the pristine white sands & turquoise waters of the Gulf.

Family · Location · Shared spaces

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!!!!

Location · Family · Comfort

Waterfront 2BR 2BA | Pool - 10 min walk to Beach

A spacious first-floor 2-bedroom, 2-bathroom condo with direct pool access and stunning bayfront views. Located just a 10-minute walk to the beach, this beautifully appointed retreat offers the perfect blend of comfort, relaxation, and convenience. Enjoy a private patio overlooking the bay, a fully equipped kitchen, and a bright, open living space. With resort-style amenities, including a pool, hot tub, and tennis courts, it’s an ideal escape for couples, families, and remote workers.

Family · Location · Decor

Beach Don't Kill My Vibe by Beach Boutique Rentals

*Features include* * Modern vacation rental directly on Pine Ave! * King bedroom with TV * Queen bedroom with TV * Bathroom with walk in shower * Small kitchenette with full-size refrigerator * Private deck with table and umbrella * Private back yard with putting green and outdoor seating * Off-street parking for one vehicle * Trolley stop across the street * Walkable to all shops and restaurants on Pine Avenue * Beach chairs, umbrella, and cart * Steps to the beach!

Location · Family · Kitchen

Newly Remodeled Beachfront Studio - On the sand!

ONE SHELL COVE on Anna Maria Island has been totally remodeled after Hurricanes Helene and Milton. Wonderful studio floor plan with amazing kitchen. Beautiful view of the waves and the beach right outside your window. Grab your towel, take a few steps and you're on the beach. The sand comes right up to your door in this ground floor unit. Amazing Location Walk to some restaurants Free Trolley goes up and down the Island Rent Kayaks and Paddleboards and enjoy the Beach

Location · Value · Indoor spaces

Just renovated, beach view from balcony Unit 203

Just renovated, a luxurious experience on the beautiful beaches and emerald waters of the Gulf of Mexico awaits you when you check into this fabulous second-floor unit. It is one of the best one-bedroom, one-bath condos on Longboat Key, offering exceptional value. While the great 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.

Family · Location · Sleep quality

On Private Beach! Full Kitchen Ground Level Unit 7

Fully remodeled in 2025! We’re back & better than ever! ON Private Beach 1 bd/1ba with breathtaking Gulf views! This 1 bedroom unit w patio leading to private beach features a full kitchen & 1 king bedroom + pullout sofa sleeping 4 guests. Smart TVs, we furnish linens, towels, toiletries, beach chairs/towels & gas grill. 1 free parking space included. For additional availability see IDENTICAL unit same location Tide Vibes #7 and 2 bedroom unit #5, sleeps 6.

Location · Family · Access

Cabin 2 at Spinnakers Vacation Cottages

My place is close to the beach, family-friendly activities, the free AMI trolley, and nightlife. You’ll love my place because of the location and the ambiance. It is nestled in the lush tropical landscape of Spinnakers Vacation Cottages. You will find Cabin 2 is a perfect spot for an island getaway. My place is good for couples, solo adventurers, families (with kids), and certain size breed and weight dogs. Spa maintains same temperature as pool.

Value · Family · Laundry

Lovely 2 bedrooms, steps away from the beach.

This tropical beach style home will greet you upon arrival, with swaying palms creating instant serenity. The property is in Bradenton Beach on Anna Maria Island. With 2 Bedrooms, 1 Bath, and a beautiful backyard. Located Just few steps away from the beautiful waters of the Gulf. Within short distance from some of the best fresh local restaurants and bars in town you will feel the tropical vibes.

Location · Family · Accuracy