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Condo vacation rentals in Longboat Key

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Top-rated condo rentals in Longboat Key

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

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Top guest favorite
Condo in Holmes Beach
4.96 out of 5 average rating, 104 reviews

Steps to the beach! Condo with pool at The Terrace

Just 200 steps from the white sands of Holmes Beach, this beautifully updated 2BR/2BA condo has everything to offer! Our unit features high-speed internet, Keurig , balconies off of each bedroom, 1-car garage, washer/dryer, heated shared pool, and access to all the beach necessities (toys, umbrellas, chairs, tent, bicycles, SUP, cart). This unit sleeps 6 (1-King, 1-Queen, & Full size sofa bed). LOCATION, LOCATION! You'll be just steps from restaurants, cafés, shops, and the free island trolley!

Top guest favorite
An aerial view captures a multi-story condominium overlooking a beach. Lush palm trees surround a heated pool area, with docks lining the waterfront. The expansive coastline is visible in the background, highlighting the scenic proximity of beach and bay.
Condo in Treasure Island
4.99 out of 5 average rating, 212 reviews

Spectacular beach to bay views from this resort.

Our condo has spectacular water views from the Bay to the Beach. We have a large one of a kind kitchen that is unique to our resort, with granite counter tops, hardwood cabinets, and all stainless steel appliances. Everything you need to prepare a meal is provided along with basic spices and condiments, Coffee, creamer, and sugar. The master bedroom has a new king size bed and walk in closet with all beach gear also available for your use. We have 2 - 50" flat screen TV's with cable as well.

Top guest favorite
Condo in Longboat Key
4.98 out of 5 average rating, 227 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 favorite
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.
Condo in Siesta Key
4.97 out of 5 average rating, 367 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 favorite
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.
Condo in Longboat Key
4.89 out of 5 average rating, 208 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 favorite
Condo in Longboat Key
4.88 out of 5 average rating, 127 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.

Guest favorite
Condo in Lido Key
4.95 out of 5 average rating, 147 reviews

Lido-Key- Tiny Studio Holiday Cottage-A

No Pets Allowed. Lido Key- 7-10 min walk to the beach & St Armands. Quaint main floor tiny (smaller than a hotel room) studio is in a Great location and an affordable way to enjoy this popular area. This cozy cottage features a Queen size bed, refrigerator, stove, microwave, coffee maker, washer & dryer, and fully stocked cooking items & dishes, Beach chairs, umbrella & towels are provided. Located at 170 Roosevelt Dr Drive, Sarasota, Fl 34236.

Guest favorite
A spacious balcony features two chairs and a round table, providing a stunning view of the Gulf. The horizon shows a clear sky above the tranquil water, with sunbathers visible along the beach. Lush greenery and a palm tree are seen framing the scene.
Condo in Indian Shores
4.93 out of 5 average rating, 149 reviews

"Jewel At The Shores" Gulf Front, sleeps 5

"Jewel at the shore"feels like you are in a snug resting place, your own nest, very homey with a breath taking Gulf view from the balcony. The gulf is right outside your door along with a year round heated pool, great on cool winter days. The unit is stocked with things you’ll need; linens, towels, shampoo et., necessities for the beach, keurig and drip coffee, some pods to get you started. New balcony and sliders. Just beautiful and comfy

Top guest favorite
An aerial view shows a two-story beachfront property with direct access to the beach. A shared pool is visible in the center, surrounded by lounge chairs. The studio unit is indicated with a blue circle on the left, featuring a patio area and proximity to the sandy beach.
Condo in Longboat Key
4.87 out of 5 average rating, 196 reviews

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.

Guest favorite
A bright living area features a comfortable light-colored sofa and armchairs, complemented by a decorative round coffee table. Large glass doors provide an unobstructed view of the beach and palm trees outside, allowing natural light to fill the space.
Condo in Indian Rocks Beach
4.97 out of 5 average rating, 154 reviews

Private Ocean View Beach Retreat with Balcony

Only steps from the beach, this newly updated and perfectly located beach condo is your luxury getaway. The large bedroom, lofty living area and modern open kitchen, as well as the generous balcony with direct view of the Gulf will make you never want to leave again. This condo is better equipped than your average vacation rental and comes with your private daily sunset spectacle. Continue to read for more...

Guest favorite
Condo in Longboat Key
4.88 out of 5 average rating, 111 reviews

Beachfront Escape – Private Balcony, Gulf Views

Beachfront Condo – No Street to Cross, Just Steps to the Sand Enjoy panoramic Gulf and sunset views from your private covered balcony in this spacious 1-bedroom, 1-bath condo on the 4th floor of Turtle Crawl Inn. Located directly on the beach in beautiful Longboat Key, FL, this unit offers unobstructed 180° views from every room and the peaceful sound of the waves just outside your door.

Guest favorite
An aerial view captures the two-story complex surrounded by lush greenery, with the intracoastal waterway adjacent to the property. The coastline is visible in the distance, framing the serene waters and community structures that line the shore.
Condo in Indian Shores
4.94 out of 5 average rating, 117 reviews

Indian Shores Beach Getaway

Amazing two bedroom, two bath condo that is steps away (literally a 2 minute walk) from the beach and the intracoastal community fishing pier and heated swimming pool! Open floor plan boasts amazing views from the private , top floor balcony of protected conservation area and intracoastal waterway. Indian Shores is a wonderful coastal community we're happy to call our 2nd home!

Popular amenities for Longboat Key condo rentals

When is the best time to visit Longboat Key?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ867ﺩ.ﺇ1,025ﺩ.ﺇ1,065ﺩ.ﺇ962ﺩ.ﺇ720ﺩ.ﺇ727ﺩ.ﺇ786ﺩ.ﺇ731ﺩ.ﺇ676ﺩ.ﺇ735ﺩ.ﺇ881ﺩ.ﺇ988
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Quick stats about condo rentals in Longboat Key

  • Total vacation rentals

    Explore 500 vacation rentals in Longboat Key

  • Nightly prices starting at

    Longboat Key vacation rentals start at ﺩ.ﺇ220 per night before taxes and fees

  • Verified guest reviews

    Over 4,360 verified reviews to help you choose

  • Family-friendly vacation rentals

    380 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Vacation rentals with a pool

    470 properties feature pools

  • Rentals with dedicated workspaces

    130 properties have a dedicated workspace

  • Wi-Fi availability

    500 of Longboat Key vacation rentals include wi-fi 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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