Longboat Key Holiday Rentals

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Holiday Rentals in Longboat Key

Sea Club I Beach Resort
3.0 star property
9.0 out of 10, Wonderful, (282)
"The unit could use an update"
Sea Club I Beach Resort
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
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
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"
Direct Beachfront Gulf with Amazing Views
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
Charming Beach Front Studio Steps to the Sand and Gulf
10.0 out of 10, Exceptional, (1)
"Quiet beach steps away, short drive ti restaurants and shops… if you’re looking to relax and enjoy the beach this location is wonderful"
Charming Beach Front Studio Steps to the Sand and Gulf
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 NZ$639
per night
17 Jun - 18 Jun
THE BEACH, condo #107, PRIVATE BEACH
Beach Front No Crossing Needed Condo Paradise. Ground Floor. Full kitchen.
9.2 out of 10, Wonderful, (37)
"We enjoyed our stay. The beach is awesome and the room was everything we needed!"
The price is NZ$523
per night
30 May - 31 May
Beach Front No Crossing Needed Condo Paradise. Ground Floor. Full kitchen.
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."
The price is NZ$502
per night
5 Jun - 6 Jun
Silver Sands #237 Resort by RVA
Updated Beachfront Condo at Prestigious Long Boat Key Resort
8.4 out of 10, Very good, (9)
"Great location!"
The price is NZ$1,395
per night
9 Jun - 10 Jun
Updated Beachfront Condo at Prestigious Long Boat Key Resort
Luxury Beach Condo with Breathtaking Views Upgraded! PROMO 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 Views Upgraded! PROMO 2024 !!,
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!
10.0 out of 10, Exceptional, (98)
"The home is well maintained and updated. The location is beyond amazing. The owner was responsive to our email questions and the property manager was excellent. We had a fabulous family vacation."
Exquisite Beachfront Villa with Private Pool & Stunning Gulf Views!
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
Beach Castle Resort, Pool, Tennis, Private Beach & Bayfront
9.8 out of 10, Exceptional, (43)
"Great time as always!"
Beach Castle Resort, Pool, Tennis, Private Beach & Bayfront
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
Silver Sands #236 Resort by RVA
9.4 out of 10, Exceptional, (59)
"Fantastic!"
The price is NZ$788
per night
14 Jun - 15 Jun
Silver Sands #236 Resort by RVA
Beachfront Incredible Panoramic Gulf View and The Most Beautiful Sunset.
9.8 out of 10, Exceptional, (118)
"Amazing views from the balcony and easy access to the beach. Location was great. Condo was very clean and had all the amenities we needed. We would definitely stay here again."
The price is NZ$635
per night
22 Jun - 23 Jun
Beachfront Incredible Panoramic Gulf View and The Most Beautiful Sunset.
Rare, 5 floor penthouse 60 feet from the sand 170 reviews
9.8 out of 10, Exceptional, (173)
"My wife and I just completed a perfect stay at this beach front property. My wife even said when we entered the room “she was never leaving”. The location, view and surrounding area was just as advertised. The communication and follow-up from the property manager was excellent! We look forward to returning soon!!"
Rare, 5 floor penthouse 60 feet from the sand 170 reviews
Silver Sands Condo on the Coast - Open Sun & Mon, $165/nt!
10.0 out of 10, Exceptional, (57)
"Condo was exactly as described, beautifully decorated (very beachy), cozy yet spacious, with a screened-in lanai overlooking a nice pool, right on the beach, and in a small condo complex with nice amenities! We loved the place and Longboat Key! Already planning a return trip! The condo was well-maintained, stocked with everything you need, and immaculately clean! Heidi is a great host, highly recommend!"
The price is NZ$596
per night
2 Jun - 3 Jun
Silver Sands Condo on the Coast - Open Sun & Mon, $165/nt!
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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
4.0 star property
8.8 out of 10, Excellent, (1001)
"Everything about this property was amazing. I just wish there were more shops/restaurants to walk to with little ones and not have to get in a car. "
The price is NZ$454
per night
12 Jun - 13 Jun
Zota Beach Resort
The Resort at Longboat Key Club
4.0 star property
8.8 out of 10, Excellent, (618)
"The attention given to me by the staff was very nice"
The price is NZ$771
per night
12 Jun - 13 Jun
The Resort at Longboat Key Club
Sea Club I Beach Resort
3.0 star property
9.0 out of 10, Wonderful, (282)
"The unit could use an update"
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Longboat Key holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Longboat Key. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Longboat Key. Seeing all the best attractions is bound to make you fall in love with Longboat Key. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Longboat Key short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Longboat Key?

Yes, there are holiday rentals close to the most popular sights in Longboat Key, or you can select a more secluded option if you're looking for a relaxing stay. 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 holiday rentals that Longboat Key has to offer?

Charming 3 Bedroom 2 Bath Home with Pool Just 2 Minutes from Anna Maria Island: This holiday home rental outside of Longboat Key is located near the beach, and has an outdoor pool, a patio and a BBQ 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 that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a garden.

How many holiday rentals are there in Longboat Key?

Choose from 196 Expedia holiday rentals in Longboat Key for a memorable holiday.

What can I see and do in Longboat Key?

Longboat Key Beaches and Jewfish Key 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 holiday rentals like in Longboat Key?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Longboat Key. Holiday rentals offer extras like WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a clean environment, holiday rentals can provide a sense of privacy away from public hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for a family trip.

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