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Longboat Key Holiday Rentals

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Our top choices for Longboat Key holiday rentals

Sunset and beach view from your balcony Unit 403

Sunset and beach view from your balcony Unit 403
Longboat Key
9.8 out of 10, Exceptional, (115 reviews)
"We arrived late in the day and found the check in process well thought out and easy. The unit was very clean, the office staff very friendly and helpful. The whole facility was very quiet. Finally, the location was great, right on the beach. "
United States
Hal S.
The price is NZ$725
includes taxes & fees
18 June - 19 June
Sunset and beach view from your balcony Unit 403

Best views of the beach from your balcony Unit 301

Best views of the beach from your balcony Unit 301
Longboat Key
9.8 out of 10, Exceptional, (91 reviews)
"Everything was great "
United States
kirt v.
The price is NZ$714
includes taxes & fees
12 June - 13 June
Best views of the beach from your balcony Unit 301

Beachfront- Longboat Key efficiency condo w/ king size bed, steps to sand.

Beachfront- Longboat Key efficiency condo w/ king size bed, steps to sand.
Longboat Key
8.4 out of 10, Very good, (20 reviews)
"The room was clean and the pool area was right on the beach. The beach itself is gorgeous, perfect for long walks, swimming and sunsets! "
United States
Lynne S.
The price is NZ$603
includes taxes & fees
14 June - 15 June
Beachfront- Longboat Key efficiency condo w/ king size bed, steps to sand.

1BR Beach Getaway – Silver Sands #254 by RVA

1BR Beach Getaway – Silver Sands #254 by RVA
Longboat Key
9.2 out of 10, Wonderful, (95 reviews)
"Great view, clean, beautiful!"
United States
Bethany
The price is NZ$842
includes taxes & fees
12 June - 13 June
1BR Beach Getaway – Silver Sands #254 by RVA

THE BEACH CONDO #107 BEACHFRONT FULL VIEW

THE BEACH CONDO #107 BEACHFRONT FULL VIEW
Longboat Key
9.8 out of 10, Exceptional, (94 reviews)
"Host was wondeful!Location and condo fabulous!"
United States
Linda D.
The price is NZ$783
includes taxes & fees
5 July - 6 July
THE BEACH CONDO #107 BEACHFRONT FULL VIEW

Relax at Gulf – Silver Sands Resort #232, Longboat

Relax at Gulf – Silver Sands Resort #232, Longboat
Longboat Key
9.2 out of 10, Wonderful, (80 reviews)
"Very happy with my stay. Room was very clean, beautifully decorated and very comfortable. Perfect efficiency! Highly recommend"
United States
Gloria
The price is NZ$802
includes taxes & fees
12 June - 13 June
Relax at Gulf – Silver Sands Resort #232, Longboat

Gulf Views – Silver Sands #250, Longboat Key by RVA

Gulf Views – Silver Sands #250, Longboat Key by RVA
Longboat Key
9.0 out of 10, Wonderful, (78 reviews)
"The host staff were very helpful."
United States
Ann S.
The price is NZ$1,133
includes taxes & fees
7 July - 8 July
Gulf Views – Silver Sands #250, Longboat Key by RVA

Luxurious Beachfront Jr. Suite by FVC

Luxurious Beachfront Jr. Suite by FVC
Longboat Key
9.4 out of 10, Exceptional, (80 reviews)
"The space was exactly as described, beautiful, comfortable, right on the beach with excellent balcony space. The kitchen has everything you need and the area is really amazing!"
United States
Debra J.
Luxurious Beachfront Jr. Suite by FVC

Are you ready for a luxury 5-floor penthouse 60 ft from water, 207 reviews

Are you ready for a luxury 5-floor penthouse 60 ft from water, 207 reviews
Longboat Key
10.0 out of 10, Exceptional, (208 reviews)
"Great location."
United States
Janet B.
The price is NZ$1,035
includes taxes & fees
13 June - 14 June
Are you ready for a luxury 5-floor penthouse 60 ft from water, 207 reviews

Updated Beachfront Condo at Prestigious Long Boat Key Resort

Updated Beachfront Condo at Prestigious Long Boat Key Resort
Longboat Key
8.4 out of 10, Very good, (19 reviews)
"Great location, and it was a clean, updated, and comfortable stay!!"
United States
Brian B.
The price is NZ$1,503
includes taxes & fees
15 June - 16 June
Updated Beachfront Condo at Prestigious Long Boat Key Resort

Roomy 2BR Retreat – Silver Sands #239 by RVA

Roomy 2BR Retreat – Silver Sands #239 by RVA
Longboat Key
9.6 out of 10, Exceptional, (48 reviews)
"Condo was great! Lots of space, clean, and great location"
United States
Sherry R.
The price is NZ$785
includes taxes & fees
19 June - 20 June
Roomy 2BR Retreat – Silver Sands #239 by RVA

Island Time on LBK!

Island Time on LBK!
Longboat Key
10.0 out of 10, Exceptional, (127 reviews)
"Great host! Amazing location. Loved the beach access and views! Highly recommended "
United States
Bonnie N.
The price is NZ$729
includes taxes & fees
26 June - 27 June
Island Time on LBK!

Bright Beach Studio – Silver Sands #255A by RVA

Bright Beach Studio – Silver Sands #255A by RVA
Longboat Key
8.8 out of 10, Excellent, (69 reviews)
"The communication was excellent and the staff very friendly. I would recommend this stay for anyone requiring a small room with easy beach access. My only negative was that the bathroomneeds updating. Overall this is a great location for beach lovers! "
United States
rebecca g.
The price is NZ$763
includes taxes & fees
15 June - 16 June
Bright Beach Studio – Silver Sands #255A by RVA

Cabana Beach Club - Beachfront Stunning Ocean View *Snow Bird Promo* Winter 2027

Cabana Beach Club - Beachfront Stunning Ocean View *Snow Bird Promo* Winter 2027
Longboat Key
9.8 out of 10, Exceptional, (268 reviews)
"The unit has a perfect balcony view of the beach. The space was very clean and comfortable with many amenities including coolers and beach umbrellas. The property provides nice lounge chairs for the beach. The host Anna was quickly responsive to our questions and needs during our visit. Highly recommend this property !"
United States
Tracey s.
The price is NZ$1,139
includes taxes & fees
20 June - 21 June
Cabana Beach Club - Beachfront Stunning Ocean View *Snow Bird Promo* Winter 2027

Drift & Dune – Longboat Beachfront #101 RVA

Drift & Dune – Longboat Beachfront #101 RVA
Longboat Key
8.6 out of 10, Excellent, (81 reviews)
"Check in and out was easy, the pool and condo were great, and the location was awesome!"
United States
Bailey B.
The price is NZ$712
includes taxes & fees
11 June - 12 June
Drift & Dune – Longboat Beachfront #101 RVA

Ocean Breeze: Open Friday, $150/nt + Fees!

Ocean Breeze: Open Friday, $150/nt + Fees!
Longboat Key
10.0 out of 10, Exceptional, (93 reviews)
"Great accommodations, excellent location, amazing host!"
United States
Ella F.
The price is NZ$604
includes taxes & fees
12 June - 13 June
Ocean Breeze: Open Friday, $150/nt + Fees!

Affordable Beach Studio – Silver Sands #257A by RVA

Affordable Beach Studio – Silver Sands #257A by RVA
Longboat Key
9.6 out of 10, Exceptional, (79 reviews)
"Right on beach-perfect for a short stay"
United States
Sean P.
The price is NZ$564
includes taxes & fees
23 June - 24 June
Affordable Beach Studio – Silver Sands #257A by RVA

Gulf-View Beachfront Condo – Unit 203 – Longboat Key

Gulf-View Beachfront Condo – Unit 203 – Longboat Key
Longboat Key
The price is NZ$638
includes taxes & fees
14 June - 15 June
Gulf-View Beachfront Condo – Unit 203 – Longboat Key

50 ft from sand, Private Island 125 +review

50 ft from sand, Private Island 125 +review
Longboat Key
10.0 out of 10, Exceptional, (134 reviews)
"Jim is a great host - he is great at communicating before, during, and at the end of the stay. The condo we stayed in was exactly as described and was wonderful!!"
United States
Robin G.
The price is NZ$1,023
includes taxes & fees
21 June - 22 June
50 ft from sand, Private Island 125 +review

Sun, Sand & Silver Sands – Gulfside Resort #237 by RVA

Sun, Sand & Silver Sands – Gulfside Resort #237 by RVA
Longboat Key
8.8 out of 10, Excellent, (43 reviews)
"Enjoyed our stay"
United States
Susan C.
The price is NZ$832
includes taxes & fees
13 June - 14 June
Sun, Sand & Silver Sands – Gulfside Resort #237 by RVA
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.
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Top Longboat Key Hotel Reviews

Find out more about Longboat Key

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, 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 NZ$603 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?

Siesta Key Island Rentals: This holiday home rental outside of Longboat Key comes with free WiFi so that you can feel at home during your trip. This holiday rental also comes with free parking to give you added peace of mind.

How many holiday rentals are there in Longboat Key?

Choose from 24 Expedia holiday rentals in Longboat Key for a memorable holiday.

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. Lido Beach and Siesta Key Beach 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.