Longboat Key Vacation Home Rentals from CA $258: Search Top Private Vacation Homes for Rent

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Longboat Key vacation homes

Ground Floor, Steps to Sand – Silver Sands #243A by RVA

Longboat Key

Sahra S.

CA $474 total

includes taxes & fees

Jun 16 - Jun 17

Kiwi Cottage~Private Heated Pool!~Shopping close!

Anna Maria

CA $1,447 total

includes taxes & fees

Jun 30 - Jul 1

Siesta Key Island Rentals

Siesta Key

Alessandra

CA $598 total

includes taxes & fees

Jun 16 - Jun 17

ChristianBNB For Teams Groups & Leaders •Sleeps 14

Sarasota Springs

CA $1,102 total

includes taxes & fees

Jun 16 - Jun 17

Casa Esquina – St. Pete | Near Beaches & Downtown

Greater Pinellas Point

CA $479 total

includes taxes & fees

Jun 17 - Jun 18

Siesta Heron Suites & Villas

Siesta Key

Christopher Robert

CA $480 total

includes taxes & fees

Jun 16 - Jun 17

"Manatee" 3 miles to Anna Marie<br>

Bradenton

Jean S.

CA $553 total

includes taxes & fees

Jun 17 - Jun 18

The Hideaways at Point Pleasant (Palm Side)

Bradenton

Diane M.

CA $438 total

includes taxes & fees

Jun 16 - Jun 17

View all properties

Find vacation rentals that suit your style

Private vacation homes

Condos

Save an average of 15% on thousands of hotels when you're signed in

Top Longboat Key Hotel Reviews

Zota Beach Resort

4/10 Poor

"If you are looking for a romantic and/or upscale vibe, this is NOT the place. We were excited to do something special for our one-year anniversary, so I called the hotel prior to our stay and told two separate people that we would be celebrating our anniversary during our stay. It sounded like the person made a note of it, but somehow it was lost. The excuse provided by the front desk was that “it’s hard when you have 300 or 400 guests…” which was probably the worst thing to tell someone who just spent an excessive amount of money to have a less than ideal time. Paying $35 for a beach umbrella (no drink service at the beach) plus a resort fee felt pretty ridiculous. We felt like we were CONSTANTLY waiting for service, which is not what you want to do for an expensive stay. At breakfast, the food was pretty disappointing and our server did not check us at all (otherwise we would have said so) and we had to flag her down for our check. She still didn’t ask how our food was. Usually if you’ve messed up in a pretty big way, the only thing you can do to even try to make it better is offer some discount/money off just as a gesture. Apologies only go so far, and since you can’t go back in time, if the hospitality side of a business has failed, they need to make it right."

Direct Beachfront Gulf with Amazing Views

10/10 Excellent

"We have stayed at Cabana for years, but this was the first time in this condo. I was concerned about the number of stairs but it wasn’t an issue at all. The beds were so comfortable and the kitchen so well stocked! You honestly can’t beat the view from this top floor condo. We love this end of the beach-literally steps away from the ocean."

THE BEACH CONDO #107 BEACHFRONT FULL VIEW

10/10 Excellent

"Beachfront!! View and location is a PERFECT! Love that you have your own patio. Can take the lounge chairs to the beach and bring back. There is an umbrella as well that can be taken to the beach.Saw dolphins in the morning right outside the condo.Lots of wildlife to watch. Ocean is beautiful. Water is clear and beautiful. Non crowded beach. Amazing restaurants nearby.Host very communicative. We will definitely be back!"

Charming 1-bedroom, beachfront condo in marvelous Longboat Key

8/10 Good

"We had just spent 6 days at a hotel in Sarasota and wanted to stay in Longboat for our last night in the area. The proximity to the beach & view from your balcony are obviously what you’re paying for here. But if I’m being honest, the owner desperately needs to update the furnishings. The couch is a very scratchy material. The bed is uncomfortable and the pillows are flat & lifeless. The TV buffered every channel we tried to watch and there are tons of cords and cables coming from behind the tv. I might expect these type of furnishings at a cheap hotel…not a 400/night beautiful beach-view condo in Longboat Key.I hope this review entices the owner to upgrade the furnishings (couch, bed, pillows, and tv in living room) so that future renters will want to stay again and again."

Country Club Long Boat Key Beach Villa 2B 3BA Pool

10/10 Excellent

"Absolutely all that we hoped for and more. I didn’t want to leave! This place will be our family go to for years to come. Elicia and Mike are superior hosts and communicators. If anything was not “to their expectation” or was rusty, broke or missing Elicia asked to let them know and it would be replaced. Nothing was wrong at all! It was clean, beautiful and exceeded expectation in every way. So many options for beaches, gorgeous pool, interesting wild life. We saw manatees two days in the gulf. I thank you for everything Elicia and Mike! Can’t wait to return."

Find out more about Longboat Key

Longboat Key Vacation Homes information

Number of reviews	1,124
Accommodation	157 Vacation Homes
Lowest Price	CA $258
Highest Price	CA $1,447

Explore a world of travel with Expedia

Flights from Toronto (YYZ) to Sarasota (SRQ)

Car rentals near Bayshore Gardens

Cortez Vacation Rentals

Book Vacation Homes in Longboat Key on Expedia.com

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Longboat Key vacation homes

Ground Floor, Steps to Sand – Silver Sands #243A by RVA