Holiday Rentals in Longboat Key

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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 reviews
"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 reviews
"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 reviews
"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 reviews
"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 review
"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
THE BEACH, condo #107, PRIVATE BEACH
9.8 out of 10, Exceptional, 55 reviews
"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 €371
includes taxes & fees
17 Jun - 18 Jun
THE BEACH, condo #107, PRIVATE BEACH
Silver Sands #237 Resort by RVA
9.0 out of 10, Wonderful, 37 reviews
"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 €292
includes taxes & fees
5 Jun - 6 Jun
Silver Sands #237 Resort by RVA
Spacious 2BR Condo, Longboat Key Cranes Bay
10.0 out of 10, Exceptional, 4 reviews
"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
Updated Beachfront Condo at Prestigious Long Boat Key Resort
8.4 out of 10, Very good, 9 reviews
"Great location!"
The price is €802
includes taxes & fees
8 Jun - 9 Jun
Updated Beachfront Condo at Prestigious Long Boat Key Resort
Longboat Key beach house - 5 min walk to the beaches and top local restaurants
10.0 out of 10, Exceptional, 6 reviews
"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
Exquisite Beachfront Villa with Private Pool & Stunning Gulf Views!
10.0 out of 10, Exceptional, 99 reviews
"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!
Beach Front No Crossing Needed Condo Paradise. Ground Floor. Full kitchen.
9.2 out of 10, Wonderful, 37 reviews
"We enjoyed our stay. The beach is awesome and the room was everything we needed!"
Beach Front No Crossing Needed Condo Paradise. Ground Floor. Full kitchen.
Charming Beach Front Studio Steps to the Sand and Gulf
10.0 out of 10, Exceptional, 2 reviews
"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 on Longboat Key #104 Resort by RVA
9.0 out of 10, Wonderful, 92 reviews
"Very pleasant stay."
The Beach on Longboat Key #104 Resort by RVA
Silver Sands #236 Resort by RVA
9.4 out of 10, Exceptional, 59 reviews
"Fantastic!"
The price is €425
includes taxes & fees
14 Jun - 15 Jun
Silver Sands #236 Resort by RVA
Rare, 5 floor penthouse 60 feet from the sand 170 reviews
9.8 out of 10, Exceptional, 173 reviews
"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
Luxury Beach Condo with Breathtaking Views Upgraded! PROMO 2024 !!,
9.8 out of 10, Exceptional, 216 reviews
"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 !!,
Silver Sands Condo on the Coast - June Dates Open!
10.0 out of 10, Exceptional, 57 reviews
"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 €380
includes taxes & fees
28 Jun - 29 Jun
Silver Sands Condo on the Coast - June Dates Open!
Silver Sands #239 Resort by RVA
9.4 out of 10, Exceptional, 45 reviews
"A friend and I stayed for a very quick weekend getaway. The location is beautiful, the room was well taken care of, clean, and nicely renovated. We were down for an engagement party at another house near there and did not check in until later. The staff was very helpful with this process and called with updates and process before we arrived. I would recommend staying here and will be looking to come back for a longer stay."
Silver Sands #239 Resort by RVA
Beach Castle Resort, Pool, Tennis, Private Beach & Bayfront
9.8 out of 10, Exceptional, 43 reviews
"Great time as always!"
Beach Castle Resort, Pool, Tennis, Private Beach & Bayfront
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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, 1,003 reviews
"In the future Opal shall have a reward system like Marriott "
The price is €298
includes taxes & fees
12 Jun - 13 Jun
Zota Beach Resort
The Resort at Longboat Key Club
4.0 star property
8.8 out of 10, Excellent, 619 reviews
"The attention given to me by the staff was very nice"
The price is €478
includes taxes & fees
10 Jun - 11 Jun
The Resort at Longboat Key Club
Sea Club I Beach Resort
3.0 star property
9.0 out of 10, Wonderful, 282 reviews
"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.

Everything you need to know about Longboat Key holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Longboat Key holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Longboat Key holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Longboat Key holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Longboat Key holiday rentals we have selected for you start as low as €292 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Longboat Key rentals

At Expedia, we put the best Longboat Key holiday 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 holiday.

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 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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