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Holiday rentals in Longboat Key

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Top-rated holiday rentals in Longboat Key

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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).

Guest favourite
A stylish living room is presented, featuring a comfortable gray sofa paired with a decorative round coffee table. Brightly colored wallpaper adorned with shell patterns enhances the space, while large windows allow natural light to filter in, complemented by light-colored flooring.
Apartment in Bradenton
4.92 out of 5 average rating, 130 reviews

Beach & Bay Walk | 5 Minutes to AMI

Experience the ultimate beachside retreat in this newly renovated 1/1 condo, located within walking distance to the serene beauty of Palma Sola Causeway Parks Bayfront beach, jet-ski rentals, and horseback riding and also a quick drive/bike from the beaches of Anna Maria Island. This well-positioned condo offers the perfect balance of convenience and tranquility, providing easy access to the natural wonders of the island and the vibrant attractions nearby, including canal fishing, jet skis, etc.

Top guest favourite
Apartment in Bradenton Beach
4.92 out of 5 average rating, 204 reviews

Beachfront condo in paradise with hot tub AMI

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

Top guest favourite
Flat in Sarasota
5 out of 5 average rating, 237 reviews

Luxurious Private Apartment in a House Near Siesta

Large modern construction 950 sq ft 1 bedroom apartment. Beautifully furnished apartment attached to the side of the main house. This upstairs unit has a private entrance with a modern interior & high ceilings. The apartment offers 1 King bed, full kitchen, a bathroom w shower, a washer and dryer, 2 tvs. Nestled on a quiet street with easy access to Siesta Key. Located 1 mile from the Stickney Point bridge with easy access to Siesta Key on . Guest must be able to climb one flight of stairs

Top guest favourite
A private stock tank pool is surrounded by a wooden deck and lounge chairs. An umbrella provides shade over the pool area. Colorful towels and a stylish table with refreshments are visible, set amidst a landscaped courtyard with lush greenery.
Guest house in Sarasota
4.99 out of 5 average rating, 257 reviews

Magical Guesthouse 1 mi from SRQ airport

@Aloe_Stranger Dreamy + fresh! This 1-bedroom guesthouse has a king bed, full bath, kitchen, washer/dryer, daybed + sleeper sofa. NEW STOCK TANK POOL! Full of style - it feels like you're in your own art installation. 1 mile from SRQ Airport, it boasts a great location as well cushy comforts. 1/2 mile from Sarasota Bay, 15 min from Lido Beach, 15 min from Siesta Key and many beaches around the Sarasota/Bradenton area. 10 min from downtown Sarasota, 1 mile from the historic Ringling Museum

Top guest favourite
Apartment in Longboat Key
4.99 out of 5 average rating, 166 reviews

Oceanside LBK: Sunny Days!

This charming seaside condo is 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 one-bedroom condo is optimal for sunset viewing from a private, screened lanai. Take a 30-second walk to the pool and secluded beach. Enjoy a relaxing vacation at our peaceful condo at Silver Sands Gulf Beach Resort! To see all four of our listings, click on my Host photo and scroll down...!

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, 203 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, 125 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 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.
Apartment in Longboat Key
4.87 out of 5 average rating, 195 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.

Top guest favourite
A studio apartment features a king bed against a light wall, complemented by a cozy seating area with a gray sofa and a chair nearby. Two round coffee tables sit on a neutral rug, with a wall-mounted smart TV and built-in shelves adding practical style.
Flat in Arlington Park
4.97 out of 5 average rating, 194 reviews

Studio Minutes to Siesta key, Lido Key, and SMH!

Enjoy sunny Sarasota, FL in our studio apartment. Located between Siesta Key and Lido Key. You can walk to Southside Village, Sarasota Memorial Hospital (SMH) and Arlington Park. Enjoy the beautiful neighborhood and easy access to Legacy Trail. Approximate driving times to popular local destinations: Siesta Key - 10 minutes Lido Key - 14 minutes SRQ airport - 15 minutes St Armands - 10 minutes Downtown - 7 minutes

Top guest favourite
A bright kitchen is showcased, featuring modern cabinetry and appliances. A small dining area with two wooden stools is positioned next to a white countertop. Natural light fills the space through a nearby door and window, creating an open atmosphere.
Home in Cove
4.99 out of 5 average rating, 121 reviews

Tranquility on the bay.

Tucked away from the hustle and bustle, my mobile home is located in a very unique neighborhood right on the bay with a little beach 2 min. down the road from my house, where you can sit and enjoy the views or fish. The homes are a combination of mobile homes like mine and houses with the most wonderful people of all walks of life. Very quiet, very safe and friendly. 5 min. to Bradenton beach and 10 min. to AMI.

Popular amenities for Longboat Key holiday rentals

When is the best time to visit Longboat Key?

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Avg. price£176£200£200£183£143£146£154£145£134£145£166£185
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Frequently Asked Questions

  • What are the best places to stay in Longboat Key?

    Guests often look for vacation rentals near the Gulf beaches or around the bay side for convenient access to water activities and dining. The north and south ends of the island are frequently suggested for their laid-back atmosphere and scenic views.

  • What are the best things to do in Longboat Key with kids?

    Families frequently explore the beaches for shell collecting and gentle waves, walk the nature trails at Joan M. Durante Park, or try paddleboarding in calm waters. Many local restaurants have kid-focused menus and outdoor seating.

  • What are some of the best things to do in Longboat Key?

    Enjoy white sand beaches, explore the natural habitats at Joan M. Durante Park, or rent a kayak for a peaceful paddle along the shoreline. The island’s local restaurants and small galleries also capture the coastal community’s character.

  • How is the weather in Longboat Key?

    Longboat Key has mild winters around 51–72°F (10–22°C), with spring bringing warmer, pleasant days. Summers become hot and humid, reaching up to 91°F (33°C), and occasional rainfall is common from late spring through early autumn.

  • When is the best time to visit Longboat Key?

    Late winter through spring is often recommended for dry, mild weather with temperatures around 55–83°F (13–28°C). Summer and early autumn bring higher humidity and rainfall, but also lush landscapes and fewer crowds.

  • What are the best places to visit in Longboat Key?

    The island has scenic beaches, the Joan M. Durante Park with its boardwalks and gardens, and a lively waterfront area with local shops and restaurants. Exploring the bay by kayak or paddleboard is also frequently suggested.

  • What are some hiking trails in Longboat Key?

    Explore the Joan M. Durante Park trails, which wind through native gardens and mangrove forests, or wander the pathways at local preserves for birdwatching and views of Sarasota Bay. Trails are generally flat and suitable for all ages.

  • What are some family activities we can do in Longboat Key?

    Families often enjoy shelling on the beach, picnicking at local parks, or spotting wildlife along the trails at Joan M. Durante Park. Guided kayak tours and casual bike rides are also popular with visitors of all ages.

  • What are some of the best day trip ideas from Longboat Key?

    Explore nearby Sarasota's art museums or lively downtown, visit historic fishing villages around the area, or discover the natural beauty of nearby nature preserves. Barrier islands and gardens just outside Longboat Key are also often recommended.

  • Are there any pet friendly accommodations available in Longboat Key?

    Many vacation rentals on Longboat Key welcome pets, particularly in beachside cottages and private homes. Local parks and outdoor dining spaces often include dog-friendly areas, making it easy to explore together.

  • What are some local tips for visiting Longboat Key?

    Consider bringing sun protection and reusable water bottles, as much of life on Longboat Key happens outdoors. Many shops and restaurants have a relaxed dress code, and exploring the island by bike is often recommended for a leisurely pace.

  • What is Longboat Key known for?

    Longboat Key is known for its tranquil Gulf beaches, locally inspired seafood, and serene natural preserves like Joan M. Durante Park. The island has a relaxed atmosphere, often attracting those looking for a coastal retreat.

  • What are the best hidden gems to explore in Longboat Key?

    Seek out quiet beach access points for peaceful shoreline walks, or visit local nature preserves with boardwalks through mangroves. Art galleries and small family-run restaurants around the island often highlight coastal traditions.

  • What are the best foods to try in Longboat Key?

    Longboat Key is known for fresh seafood like grouper sandwiches, stone crab, and shrimp prepared with local flavors. Key lime pie is a frequently suggested dessert, and many spots feature locally sourced produce and citrus.

  • What should I bring for a trip to Longboat Key?

    Pack swimwear, light layers, comfortable sandals, and sun protection such as sunglasses and a hat. A reusable water bottle and beach gear like a towel or snorkel set can help you make the most of the coastal setting.

  • What is the nightlife in Longboat Key like?

    Longboat Key has a relaxed nightlife scene, with waterfront bars, live music at local restaurants, and venues that feature sunset views. Many visitors enjoy low-key evenings and outdoor lounges rather than late-night clubs.

  • What are the most popular events or festivals in Longboat Key?

    Seasonal art fairs, seafood festivals, and holiday boat parades are frequently suggested activities in and around Longboat Key. Community markets and cultural events often take place during the cooler months.

  • Are there family friendly vacation rentals in Longboat Key?

    Longboat Key has a variety of family friendly vacation rentals, including multi-bedroom homes, condos with pools, and properties near beaches or parks. Kid-focused amenities such as full kitchens and outdoor spaces are commonly available.

Quick stats about holiday rentals in Longboat Key

  • Total holiday rentals

    Explore 1,010 holiday rentals in Longboat Key

  • Nightly prices starting at

    Longboat Key holiday rentals start at £22 per night before taxes and fees

  • Verified guest reviews

    Over 11,250 verified reviews to help you choose

  • Family-friendly holiday rentals

    780 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 170 rentals that welcome pets

  • Holiday rentals with a pool

    830 properties feature pools

  • Rentals with dedicated workspaces

    380 properties have a dedicated workspace

  • Wifi availability

    990 of Longboat Key holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Self check-in, Free parking on premises and Beachfront across Longboat Key rentals

  • 4.8 Average rating

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

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Manatee County
  5. Longboat Key