Beachfront holiday rentals in Longboat Key

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Top-rated beachfront rentals in Longboat Key

Guests agree: these beachfront homes are highly rated for location, cleanliness and more.

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Top guest favourite
Tall grasses gently sway in the foreground, framing a serene beach scene. Soft waves lap against the shore, reflecting hues of orange, pink, and purple from the sunset sky. Cloud formations add depth to the view, enhancing the tranquility of the coastal landscape.
Flat in Longboat Key
4.96 out of 5 average rating, 114 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).

Top guest favourite
A large window reveals a stunning view of the sunset over the Gulf. Two red adirondack chairs are positioned to face the ocean, inviting relaxation. The soft glow of the setting sun reflects on the water, creating a serene atmosphere in the living space.
Apartment in Bradenton Beach
4.92 out of 5 average rating, 206 reviews

Beachfront Anna Maria Island w hot tub & Gulf view

You only have to go down 14 stairs from your second-floor beachfront condo to have your toes in the powder soft sand. A queen size bed with a soft mattress in the bedroom and a queen size pullout couch in the living room. Full kitchen in the unit and laundry available downstairs. Cable and high-speed internet included. One assigned parking spot. Enjoy the sunset from your balcony as it sinks into the Gulf. Perfect for a romantic couple getaway or bring the kids for a fun stay at the beach

Guest favourite
Apartment in Longboat Key
4.88 out of 5 average rating, 111 reviews

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.

Superhost
Home in Longboat Key
4.86 out of 5 average rating, 137 reviews

Summer House longboat key

Luxurious waterfront home with bay and and canal view, new custom kitchen with a view to the pool and your own private tiki bar, dock that can accommodate up to 21 ft boat , whole house just received a complete inside and out make over. Tropical coconut palms, outside patio and grill. Fish on the dock and watch dolphins and manatee. Truly a tropical paradise just 7 minute Walk to your own private beach. minutes from St Armand’s circle. feel free to reach out with any questions or requests

Top guest favourite
A dining setting on a patio table showcases a plate of breakfast foods, including a toasted bagel, fruit, and a drink. Soft, rolled towels are stacked nearby, with a view of the beach and pool visible in the background.
Apartment in Longboat Key
4.98 out of 5 average rating, 222 reviews

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...!

Top guest favourite
A view from the balcony captures a stunning sunset over the Gulf, where vibrant hues blend in the sky. The sandy beach is visible below, with a winding path leading to the shoreline. Figures can be seen strolling along the beach, adding life to the serene scene.
Flat in Independence Square
4.96 out of 5 average rating, 183 reviews

Direct Ocean View Top Floor Renovated. 2BR, 2 Bath

The Marquise 204 is a Beautiful 1300sq ft DIRECT beachfront unit! Direct Gulf front views! Top floor corner unit. Small and quiet 10-unit building. Tremendous location for getaways with family and friends. After arriving you can literally leave your car behind and walk to over 10 local restaurants, bars and shops! Enjoy some of the best sunsets you will see in all of Florida from your private balcony! NO PETS. Renter MUST be at least 25 years old. NOTE: TWO flights of stairs NO elevator.

Top guest favourite
A sandy path leads through lush greenery towards the beach, framed by overhanging branches. The ocean is visible in the distance, with light reflecting off the water. Shadows create a peaceful atmosphere as the sun casts a warm glow.
Cottage in Indian Shores
4.96 out of 5 average rating, 183 reviews

Beautiful Beachfront Cottage on the Water

Renovated, romantic 1937 beach front cottage. Last of its kind in the quiet family setting of Indian Shores Florida, halfway between Clearwater Beach and Treasure Island/John's Pass. Truly an "Old Florida" experience with original pine floors, Florida room and covered porches, as well as updated kitchen and bathroom. This house, uniquely built near ground level, allows it to be waterfront on the beach while shaded by huge pine trees. You won't find a more tranquil setting on the beach.

Top guest favourite
A private patio with a round wooden table and two chairs overlooks a manicured lawn leading to the beach. Palm trees sway gently beside the outdoor seating area, offering a serene view of the Gulf waters in the background.
Apartment in Siesta Key
4.97 out of 5 average rating, 361 reviews

On the Beach; Siesta Key SunBum Studio

Welcome back to paradise ! STEPS to your private beach without the tricks or gimmicks found elsewhere on the Siesta Key. This is the only studio in the Palm Bay Club tower on ground level with breathtaking views of the white sand and gulf waters. The Palm Bay Club offers 2 pools, hot tub, gym, boat docks, fishing pier, outdoor grills, tennis/pickle ball courts; not to mention FREE parking+ beach lounge chairs. If we are booked check out our additional units under our profile.

Guest favourite
A screened lanai offers poolside views, with vibrant orange and blue chairs positioned to enjoy the scenery. Lush greenery borders the area, while palm trees sway in the gentle breeze. Glimpses of the Gulf of Mexico and a heated pool are visible through the railing.
Apartment in Longboat Key
4.9 out of 5 average rating, 206 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 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.

Guest favourite
Flat in Bradenton Beach
4.91 out of 5 average rating, 137 reviews

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

Guest favourite
Apartment in Longboat Key
4.88 out of 5 average rating, 126 reviews

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.

Top guest favourite
An aerial view showcases a cluster of charming two-story homes nestled near the beach. The golden hues of the sunset reflect off the water, while the sandy shore and gentle waves create a serene coastal atmosphere.
Bungalow in Indian Shores
5 out of 5 average rating, 228 reviews

Quiet Beachfront Bungalow on Florida’s Gulf Coast

Welcome to The Sunset Beach Bungalow! This top-floor luxury water-front home located in Indian Shores, FL has been completely remodeled. Our serene getaway is situated on the Gulfs Coast. The large deck looks out over the water, providing a calming sanctuary to which you can retreat any time of day or night. Our home is over 1000 sq. ft and is newly furnished with plenty of room to relax during your stay. Our beach is private so there aren’t large crowds!

Popular amenities for beachfront rentals in Longboat Key

When is the best time to visit Longboat Key?

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Avg. price$489 SGD$549 SGD$563 SGD$494 SGD$331 SGD$371 SGD$363 SGD$322 SGD$319 SGD$347 SGD$358 SGD$441 SGD
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Quick stats about beachfront rentals in Longboat Key

  • Total holiday rentals

    Explore 130 holiday rentals in Longboat Key

  • Nightly prices starting at

    Longboat Key holiday rentals start at $76 SGD per night before taxes and fees

  • Verified guest reviews

    Over 2,690 verified reviews to help you choose

  • Family-friendly holiday rentals

    100 properties offer extra space & child-friendly amenities

  • Holiday rentals with a pool

    120 properties feature pools

  • Rentals with dedicated workspaces

    70 properties have a dedicated workspace

  • Wifi availability

    130 of Longboat Key holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Longboat Key rentals

  • 4.8 Average rating

    Longboat Key stays are highly rated by guests – averaging 4.8 out of 5!

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