Longboat Key Vacation Rentals

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Vacation Rentals in Longboat Key

Sea Club I Beach Resort
On the beach, white sand
Sea Club I Beach Resort
3.0 star property
9.0 out of 10, Wonderful, (284)
"Nice place for a quiet, short getaway "
Sea Club I Beach Resort
Gorgeous condo on the beautiful Longboat Key beach.Next door #9 also available.
On the beach, sun loungers, beach towels
Gorgeous condo on the beautiful Longboat Key beach.Next door #9 also available.
9.8 out of 10, Exceptional, (129)
"Really cute fun place to stay enjoyed the beach the pool and the amazing sunsets My husband and I had such a good time"
Gorgeous condo on the beautiful Longboat Key beach.Next door #9 also available.
Breathtaking Beach Front Property Ground Floor Condo
On the beach, beach umbrellas
Breathtaking Beach Front Property Ground Floor Condo
9.6 out of 10, Exceptional, (120)
"This was a perfect location.Beautiful location would like to reserve for next year.At the same time if stay there many more times, Everyone was very Nice and helpful"
Breathtaking Beach Front Property Ground Floor Condo
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Direct Beachfront Gulf with Amazing Views
Property grounds
Direct Beachfront Gulf with Amazing Views
9.8 out of 10, Exceptional, (84)
"we had a great stay , the view was fantastic from the unit and the sunsets was amazing. It was just as it was listed. The amenities was great in the unit. and very comfortable. Had an issue with ac but it was addressed and fixed right away"
The price is $475
$954 total
includes taxes & fees
Jun 15 - Jun 16
Direct Beachfront Gulf with Amazing Views
THE BEACH, condo #107, PRIVATE BEACH
Sun loungers, beach towels
THE BEACH, condo #107, PRIVATE BEACH
9.8 out of 10, Exceptional, (55)
"Gorgeous beach and the room is right on the beach. Great patio area with grill.. And there are rabbits that hop around outside your back. Door it was the cutest thing ever! Love this place we'll be back!"
The price is $199
$393 total
includes taxes & fees
Jun 17 - Jun 18
THE BEACH, condo #107, PRIVATE BEACH
Waterfront home with private beach, a private pool, and water activities! Moku
On the beach
Waterfront home with private beach, a private pool, and water activities! Moku
10.0 out of 10, Exceptional, (1)
"We were searching for a unique vacation experience when we came across this listing on Vrbo, which definitely did not disappoint. It’s on an island with a very secluded beach surrounding it! You literally have to take a boat there, how cool is that and the wooden walkways all over really had a vibe! Our group really enjoyed our trip to the Anna Maria Island area, great food and shops, nice people, fanastic beaches. It was so nice to have our own private retreat and pool to relax in, we felt very...
Waterfront home with private beach, a private pool, and water activities! Moku
Luxury Beach Condo with Breathtaking PROMO175-MAY24-26-2024
Exterior
Luxury Beach Condo with Breathtaking PROMO175-MAY24-26-2024
9.8 out of 10, Exceptional, (216)
"We practically lived on the beautiful Gulf-view lanai, the view is outstanding! And there's nothing better that starting the day with coffee and ending it with wine on the porch while listening to the waves. A wonderful place to unwind for a long weekend - very clean, has all the necessities, great location. It was a total delight!"
Luxury Beach Condo with Breathtaking PROMO175-MAY24-26-2024
Spacious 2BR Condo, Longboat Key Cranes Bay
Beach
Spacious 2BR Condo, Longboat Key Cranes Bay
10.0 out of 10, Exceptional, (4)
"Spacious condo and appreciated the layout for privacy between the MBR and the twin bedroom. Enjoyed the porch access off the MBR and the FR. Spacious/ updated kitchen also with another separate balcony and breakfast table. Incredibly private and quiet. Perfect walk across the street to the beach ( no life guard beach but you have several public beaches within 15 mins either in Anna Marie island or at Lido beach). The pool is clean and warm. So loved the evening entertainment with the pod of...
Spacious 2BR Condo, Longboat Key Cranes Bay
Exquisite Beachfront Villa with Private Pool & Stunning Gulf Views!
Aerial view
Exquisite Beachfront Villa with Private Pool & Stunning Gulf Views!
10.0 out of 10, Exceptional, (99)
"10/10 home for our family to all get together in our favorite place on earth. Perfect for the grandkids and adults alike. Beautiful beach, lovely salt water pool, clean and beautiful home. Great setup and will definitely be coming back year after year!"
Exquisite Beachfront Villa with Private Pool & Stunning Gulf Views!
Turtle Crawl Inn
Condo #501 Beach View | Terrace/patio
Turtle Crawl Inn
3.0 star property
8.6 out of 10, Excellent, (88)
"Staff was very friendly and helpful. Everything was clean and in proper working order. A little dated but very well kept."
Turtle Crawl Inn
Silver Sands #237 Resort by RVA
On the beach
Silver Sands #237 Resort by RVA
9.0 out of 10, Wonderful, (37)
"Silver Sands is a classic Florida beachside condo complex. The property was clean and well run, with excellent proximity to the beach. It is a great option for family vacations."
Silver Sands #237 Resort by RVA
Charming Beach Front Studio Steps to the Sand and Gulf
Property grounds
Charming Beach Front Studio Steps to the Sand and Gulf
10.0 out of 10, Exceptional, (2)
"Close to beach"
Charming Beach Front Studio Steps to the Sand and Gulf
Longboat Key beach house - 5 min walk to the beaches and top local restaurants
Sun loungers, beach towels
Longboat Key beach house - 5 min walk to the beaches and top local restaurants
10.0 out of 10, Exceptional, (6)
"My husband and I enjoyed a two-week stay at this home in Longbeach Village. The home was as pictured with everything needed to make our stay hassle free. The neighborhood is lovely and quiet and close to the beach and a small shopping center with several great places to eat. It would have been helpful to have an information sheet with instructions on how to use the TV, days of trash pick up, and local suggestions. Otherwise, we had a wonderful time and would come back again."
Longboat Key beach house - 5 min walk to the beaches and top local restaurants
Beach view. Year-round Balcony Sunsets. Just renovated.
Property grounds
Beach view. Year-round Balcony Sunsets. Just renovated.
9.8 out of 10, Exceptional, (69)
"Amazing location close the beach.Quiet place to relax!!"
The price is $245
$499 total
includes taxes & fees
Jun 16 - Jun 17
Beach view. Year-round Balcony Sunsets. Just renovated.
Sunny Gulf Coast Villa: Direct Beach & Pool Access
On the beach
Sunny Gulf Coast Villa: Direct Beach & Pool Access
9.2 out of 10, Wonderful, (22)
"We had a wonderful time relaxing and playing on Longboat Key and the location and amenities at this villa were key to an exciting trip for our young family."
Sunny Gulf Coast Villa: Direct Beach & Pool Access
Beach Front No Crossing Needed Condo Paradise. Ground Floor. Full kitchen.
Beach | On the beach, sun loungers, beach towels
Beach Front No Crossing Needed Condo Paradise. Ground Floor. Full kitchen.
9.4 out of 10, Exceptional, (38)
"The condo was awesome, clean , location was perfect!!!! Does need a new mattress though We will definitely be returning again!!"
The price is $128
$319 total
includes taxes & fees
Jun 11 - Jun 12
Beach Front No Crossing Needed Condo Paradise. Ground Floor. Full kitchen.
Updated Beachfront Condo at Prestigious Long Boat Key Resort
A heated pool
Updated Beachfront Condo at Prestigious Long Boat Key Resort
8.4 out of 10, Very Good, (9)
"Great location!"
The price is $399
$858 total
includes taxes & fees
Jun 10 - Jun 11
Updated Beachfront Condo at Prestigious Long Boat Key Resort
Open Thursday, June 13th & Friday, June 14th!
On the beach, sun loungers, beach umbrellas, beach towels
Open Thursday, June 13th & Friday, June 14th!
10.0 out of 10, Exceptional, (58)
"Great place, wonderful beach, clean condo. Easy/quick driving access to shopping, fresh fish restaurants and excursions. Many wonderful amenities! Kind owner Recommendation; recycle advertisement outside and inside bin for recycling, more beach towels if longer than 3 day stay, quarter machine for laundry after hours of office, gas station refused to provide. Quite hours encouraged."
The price is $200
$416 total
includes taxes & fees
Jun 28 - Jun 29
Open Thursday, June 13th & Friday, June 14th!
Gulf Getaway with Porch + Direct Beach Access!
Property grounds
Gulf Getaway with Porch + Direct Beach Access!
9.2 out of 10, Wonderful, (31)
"Amazing location with a short walk to the pool and beach."
Gulf Getaway with Porch + Direct Beach Access!
The Beach on Longboat Key #104 Resort by RVA
On the beach
The Beach on Longboat Key #104 Resort by RVA
9.0 out of 10, Wonderful, (92)
"Very pleasant stay."
The Beach on Longboat Key #104 Resort by RVA
Don't see what you're looking for?
See all available properties in Longboat Key
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.

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

Zota Beach Resort
Breakfast, lunch and dinner served
Zota Beach Resort
4.0 star property
8.8 out of 10, Excellent, (1008)
"People and property were fantastic. Only complaint was pool service needed a few additional attendants. Loved our stay."
The price is $234
$307 total
includes taxes & fees
Jul 9 - Jul 10
Zota Beach Resort
The Resort at Longboat Key Club
Exterior
The Resort at Longboat Key Club
4.0 star property
8.8 out of 10, Excellent, (620)
"It was amazing the view is beautiful and will definitely come again "
The price is $419
$519 total
includes taxes & fees
Jun 18 - Jun 19
The Resort at Longboat Key Club
Sea Club I Beach Resort
On the beach, white sand
Sea Club I Beach Resort
3.0 star property
9.0 out of 10, Wonderful, (284)
"Nice place for a quiet, short getaway "
Sea Club I Beach Resort
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.

Everything you need to know about Longboat Key vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Longboat Key vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Longboat Key vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Longboat Key vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Longboat Key. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Longboat Key in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $128 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Longboat Key rentals

At Expedia, we put the best Longboat Key vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Longboat Key rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Longboat Key vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Longboat Key. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find a vacation rental in Longboat Key?

Yes, we have vacation rentals near popular local attractions in Longboat Key, or you can go with a secluded option if you're looking for relaxation. Nature enthusiasts will enjoy the popular beaches in Longboat Key. Make sure you have time to check out the monuments while you're in the area.

What are some of the best vacation rentals that Longboat Key has to offer?

Charming 3 Bedroom 2 Bath Home with Pool Just 2 Minutes from Anna Maria Island: This vacation home rental near Longboat Key is located near the beach and has an outdoor pool, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a garden.

How many vacation rentals are there in Longboat Key?

Choose from 183 Expedia vacation rentals in Longboat Key for a memorable vacation.

What can I see and do in Longboat Key?

Jewfish Key and Longboat Key Beaches are a couple of lovely local spots to get outside and enjoy nature. Siesta Key Beach and St. Armands Circle are other popular places to visit in the area.

What are vacation rentals like in Longboat Key?

Vacation rentals are privately owned accommodations you can stay in for several days or more in Longboat Key. Vacation rentals offer amenities like kitchens and laundry facilities so you'll have everything you need. If you're concerned about a clean environment, vacation rentals can provide a sense of seclusion away from public hotel elevators and busy reception areas while still allowing you to travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive choice for a family getaway.

Recent reviews of Longboat Key properties
Expedia verified reviews

Silver Sands Condo on the Coast - Open Sun & Mon, $165/nt!

Silver Sands Condo on the Coast - Open Sun & Mon, $165/nt!

5/5 Excellent
Silver Sands Condo
"Great place, wonderful beach, clean condo. Easy/quick driving access to shopping, fresh fish restaurants and excursions. Many wonderful amenities! Kind owner Recommendation; recycle advertisement outside and inside bin for recycling, more beach towels if longer than 3 day stay, quarter machine for laundry after hours of office, gas station refused to provide. Quite hours encouraged."
A verified traveler stayed at Silver Sands Condo on the Coast - Open Sun & Mon, $165/nt!
Posted 5 days ago
Silver Sands Condo on the Coast - Open Sun & Mon, $165/nt!