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Longboat Key Vacation Rentals

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Vacation Rentals in Longboat Key

Sea Club I Beach Resort

Sea Club I Beach Resort

3 out of 5
4141 Gulf of Mexico Drive, Longboat Key, FL

This Longboat Key apartment building is on the beach, 2.8 mi (4.4 km) from Cannons Marina, and within 6 mi (10 km) of Coquina Beach and Beer Can Island. Cortez ...

4.5/5Wonderful! (123 reviews)
Hidden Gem

"Great throw back, we loved staying here and look foward to coming back."…"

Reviewed on Aug 11, 2020

Sea Club I Beach Resort
Beach Castle Resort by RVA

Beach Castle Resort by RVA

3 out of 5
5310 Gulf of Mexico Dr, Longboat Key, FL

Nestled on the beach, this Longboat Key condo resort is within 3 mi (5 km) of Cannons Marina, Beer Can Island, and Jewfish Key. Coquina Beach and Cortez Beach ...

4.4/5Excellent! (196 reviews)
Quiet Retreat

"Much needed short stay vacation on beautiful LBK. Beach Castle is located on N end of island with great restaurants nearby, I chose to go with take out. Having chairs available on the beach was key - no lugging. Kitchen had the basics though I didn’t need much. My only recommendation is that owner ..."…"

Reviewed on Jun 29, 2020

Beach Castle Resort by RVA
Silver Sands Gulf Beach Resort by RVA

Silver Sands Gulf Beach Resort by RVA

3 out of 5
5841 Gulf of Mexico Drive, Longboat Key, FL

Offering direct access to the beach, this Longboat Key condo building is 0.3 mi (0.5 km) from Cannons Marina and 3 mi (4.7 km) from Coquina Beach. Beer Can Island ...

4.2/5Excellent! (323 reviews)

"My husband and I stayed at the Silver Sands back in 2007 when we got married, as did our wedding guests. Fast forward all these years later, and we went back for another stay at this lovely resort. First of all, Clint provided us with exceptional service, which is part of why we're continually loyal ..."…"

Reviewed on May 23, 2020

Silver Sands Gulf Beach Resort by RVA

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Casa Del Mar Longboat Key

Casa Del Mar Longboat Key

4 out of 5
4621 Gulf of Mexico Dr, Longboat Key, FL

This Longboat Key condo resort is on the beach, 6.4 mi (10.4 km) from Mote Marine Laboratory & Aquarium, and within 16 mi (25 km) of St. Armands Circle and John ...

4.7/5Exceptional! (82 reviews)

"Beautiful and peaceful vacation with family, we loved it so much, will definitely come back soon! Nice beach, beautiful Resort to stay and to in joy beautiful Florida 👍"…"

Reviewed on Aug 25, 2020

Casa Del Mar Longboat Key
Cedars East Unit #521 2br/2.5ba Condo Longboat Key- Updated- 1440 Sqft

Cedars East Unit #521 2br/2.5ba Condo Longboat Key- Updated- 1440 Sqft

Longboat Key, FL

Situated by the ocean, this condo building is 0.7 mi (1.2 km) from Cannons Marina and within 3 mi (5 km) of Beer Can Island and Jewfish Key. Coquina Beach and ...

4.7/5Exceptional! (27 reviews)
Spacious property and convenient to the beach and pool

"This was a beautiful property and very convenient to the beach and pool. Great amenities, comfortable beds and good location. A small little hiccup but nothing to sweat over. David was very easy to get in touch with and overall I had a great time and would definitely stay again."…"

Reviewed on Jul 28, 2020

Cedars East Unit #521 2br/2.5ba Condo Longboat Key- Updated- 1440 Sqft
Updated Villa Condo -steps to Beautiful White-sand Beach

Updated Villa Condo -steps to Beautiful White-sand Beach

Longboat Key, FL

Situated by the ocean, this romantic villa is 0.7 mi (1.1 km) from Beer Can Island and 1.6 mi (2.6 km) from Coquina Beach. Jewfish Key and Cannons Marina are ...

5/5Exceptional! (1 review)
Paradise

"The beach, pool, and bay were simply wonderful. We loved everything! Best vacation, especially during a pandemic, due to the private beach and pool. We didn't want to leave! We will return next year."…"

Reviewed on Jun 30, 2020

Updated Villa Condo -steps to Beautiful White-sand Beach
The Beach on Longboat Key by RVA

The Beach on Longboat Key by RVA

3 out of 5
3465 Gulf of Mexico Drive, Longboat Key, FL

Nestled on the beach, this Longboat Key condo building is within 6 mi (10 km) of Cannons Marina, Lido Beach, and Beer Can Island. Quick Point Nature Reserve ...

4.1/5Very Good! (186 reviews)

"Excelente , I will coming back with my family again"…"

Reviewed on Aug 14, 2020

The Beach on Longboat Key by RVA
Sandpiper Inn

Sandpiper Inn

2.5 out of 5
5451 Gulf of Mexico Dr, Longboat Key, FL

Situated in Longboat Key, this aparthotel is 1 mi (1.7 km) from Cannons Marina and within 3 mi (5 km) of Beer Can Island and Jewfish Key. Coquina Beach and Coquina ...

5/5Exceptional! (4 reviews)

"Perfect location, clean and beautiful"…"

Reviewed on Jul 26, 2020

Sandpiper Inn
Turtle Crawl Inn

Turtle Crawl Inn

3 out of 5
4235 Gulf Of Mexico Drive, Longboat Key, FL

This Longboat Key condo building is on the beach, 2.7 mi (4.3 km) from Cannons Marina, and within 6 mi (10 km) of Coquina Beach and Beer Can Island. Cortez Beach ...

4.1/5Very Good! (61 reviews)

"We had a great time! Loved the access to the beach and the umbrella and lounges available at no extra charge. Cozy, quiet and comfortable. Will come back again, hoping the weather is just as nice too..."…"

Reviewed on Jun 20, 2020

Turtle Crawl Inn
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Choosing the perfect Longboat Key rental

You don't have to give up the privacy of your own residence. Book a vacation rental instead of a hotel and avoid the crowds. Reserve one of Longboat Key's 10 vacation rentals now on Expedia.com.

Foodies, animal lovers, and shoppers are in for a treat, while all visitors will find something at this relaxing beach destination to delight in. Families will find plenty of fun activities in the area, including boating. Grown-ups might be interested in watching a romantic sunrise.

Dining in Longboat Key

Longboat Key is recognized for its cafés. If you'd rather eat in, that's simple too, since most vacation rentals come with full-size kitchens.

Sightseeing around Longboat Key

Some top sights around Longboat Key include University of South Florida Sarasota, Mote Marine Aquarium, and John and Mable Ringling Museum of Art. You can easily spend a leisurely day (or days) in the sunshine at Beer Can Island, Siesta Key Public Beach, or Cortez Beach. Enjoy a leisurely day of shopping at St. Armands Circle or Bay Isles Shopping Center. Unwind in the green spaces with stops at Sarasota Jungle Gardens and Marie Selby Botanical Gardens. For more things to do, spend the day at Cannons Marina or Marina Jack.

Packing for your Longboat Key trip

Whether your trip is short or long, you can use the following seasonal average temperatures to decide what to bring.

  • January–March: 64°F
  • April–June: 77°F
  • July–September: 82°F
  • October–December: 70°F

Booking your rental on Expedia

Book your vacation rental in Longboat Key easily and safely on Expedia. We can help you get in touch with the property owner to make special arrangements. With the convenience of a short-term rental, you're sure to have a memorable trip.

Other types of properties in Longboat Key you may be interested in

Zota Beach Resort

Zota Beach Resort

4 out of 5
4711 Gulf of Mexico Dr, Longboat Key, FL
Free CancellationReserve now, pay when you stay
The price is $161 per night from Sep 27 to Sep 28
Zota Beach Resort
The Resort at Longboat Key Club

The Resort at Longboat Key Club

4 out of 5
220 Sands Point Road, Longboat Key, FL
The price is $297 per night from Oct 1 to Oct 2
The Resort at Longboat Key Club
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.