Vacation Rentals in Longboat Key, Sarasota
Large selection of Apartment Rentals in Clearwater, book your Rental here and save!
Many properties to choose from, including private Homes, Cottages or Condos with Wi-Fi, Pool, Oceanview, Beachfront and other amenities that will make your Clearwater Florida visit the perfect getaway.
Start your vacation here!
Start your vacation here!
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Apartment Rental
10.0 Star Review
Longboat Key, Florida
2 Bedrooms
2 Bath(s) Sleeps 6
Sea Grape Inn #5- Beachfront Property
Apartment Rental
9.6 Star Review
Longboat Key, Florida
2 Bedrooms
2 Bath(s) Sleeps 4
Sea Grape Inn #4- Beachfront Property
Apartment Rental
9.8 Star Review
Longboat Key, Florida
2 Bedrooms
2 Bath(s) Sleeps 6
Sea Grape Inn #7 - Beachfront Property
Condo Rental
10.0 Star Review
Longboat Key, Florida
2 Bedrooms
2 Bath(s) Sleeps 6
Luxury Condo located on Beachfront Property
Condo Rental
9.6 Star Review
Longboat Key, Florida
2 Bedrooms
2 Bath(s) Sleeps 6
On the beach, Sunset view, Monthly rental 2B/B2 Pool&Tennis
Condo Rental
Longboat Key, Florida
2 Bedrooms
2 Bath(s) Sleeps 4
Stunning 2 BR Condo views of the Gulf and Lake
Villa Rental
9.8 Star Review
Longboat Key, Florida
2 Bedrooms
1 Bath(s) Sleeps 4
Longboat Key Florida Condo. Walk to beach, bay & rsstaurants.
Condo Rental
10.0 Star Review
Longboat Key, Florida
2 Bedrooms
2 Bath(s) Sleeps 6
1st Floor Home Away from Home - Steps to Beach - Pool
Condo Rental
9.8 Star Review
Longboat Key, Florida
2 Bedrooms
2 Bath(s) Sleeps 6
Exclusive Beach-Style Condo with great Gulf-View ? Sand Cay 206, Longboat Key
Condo Rental
9.6 Star Review
Longboat Key, Florida
2 Bedrooms
2 Bath(s) Sleeps 4
2/2 Beachfront, VIEWS, Pool, Private Beach Access
Condo Rental
Longboat Key, Florida
2 Bedrooms
2 Bath(s) Sleeps 4
Beautiful Longboat Key Condo Surrounded by Ocean
Private Home Rental
10.0 Star Review
Longboat Key, Florida
3 Bedrooms
2 Bath(s) Sleeps 6
UPDATED GORGEOUS CANAL SOUTH END LBK PROPERTY WALK TO BEACH SHOPPING CLOSE BY
Condo Rental
9.8 Star Review
Longboat Key, Florida
2 Bedrooms
1 Bath(s) Sleeps 6
Charming Cabana Beach Club #8 - Your Coastal retreat Awaits!#9 also available.
Condo Rental
9.8 Star Review
Longboat Key, Florida
2 Bedrooms
2 Bath(s) Sleeps 6
GULF FRONT CONDO / PRIVATE PATIO / STEPS TO THE BEACH
Private Home Rental
8.0 Star Review
Longboat Key, Florida
2 Bedrooms
2 Bath(s) Sleeps 4
Peaceful Longboat Key Canal Home
Condo Rental
Longboat Key, Florida
2 Bedrooms
2 Bath(s) Sleeps 4
Gorgeous Beachside Condo in superior Longboat Location
Condo Rental
9.0 Star Review
Longboat Key, Florida
1 Bedrooms
1 Bath(s) Sleeps 4
Longboat Key Club!! Direct Beachfront!!
Condo Rental
9.2 Star Review
Longboat Key, Florida
2 Bedrooms
2 Bath(s) Sleeps 6
Unit #207 Sand Cay Beach Resort Pool View
Cottage Rental
10.0 Star Review
LongBoat Key, Florida
3 Bedrooms
2 Bath(s) Sleeps 8
FANTASTIC COTTAGE- SLEEPS 8! - LONGBOAT KEY FL - ENTIRE WEEK OF 3/29 - 4/5 2025
Private Home Rental
10.0 Star Review
Longboat Key, Florida
4 Bedrooms
4 Bath(s) Sleeps 8
Hidden Bay/Beach Paradise
Condo Rental
9.6 Star Review
Longboat Key, Florida
2 Bedrooms
2 Bath(s) Sleeps 6
2/2 Beachfront, VIEWS, Pool, Private Beach Access
Condo Rental
9.8 Star Review
Longboat Key, Florida
2 Bedrooms
2 Bath(s) Sleeps 4
2/2 Beachfront, VIEWS, Pool, Private Beach Access
Condo Rental
10.0 Star Review
Longboat Key, Florida
2 Bedrooms
2 Bath(s) Sleeps 4
PENTHOUSE DOUBLE BALCONY FULL GULF & BAY VIEWS FROM EVERY ROOM Beachplace 5-602
Apartment Rental
10.0 Star Review
Longboat Key, Florida
2 Bedrooms
2 Bath(s) Sleeps 6
Sea Grape Inn #1- Beachfront Property
Condo Rental
9.4 Star Review
Longboat Key, Florida
2 Bedrooms
2 Bath(s) Sleeps 6
Float Above The Waves In Paradise - Beach Front, 2 Bed, 2 Bath
Condo Rental
9.8 Star Review
Longboat Key, Florida
2 Bedrooms
2 Bath(s) Sleeps 6
Wonderful beach condo, heated pool, peaceful location Longboat Key
Apartment Rental
9.4 Star Review
Longboat Key, Florida
Studio
1 Bath(s) Sleeps 2
1/1 Beachfront, VIEWS, Pool, Private Beach Access
Private Home Rental
Longboat Key, Florida
3 Bedrooms
2 Bath(s) Sleeps 6
Longboat Key Waterfront: Private Heated Pool w/ Soaking End & Luxury Hot Tub!
Private Home Rental
9.8 Star Review
Longboat Key, Florida
4 Bedrooms
4 Bath(s) Sleeps 10
Private Island Retreat with Private Beach, Dock, Palm Trees & Glorious Sunsets
Private Home Rental
9.6 Star Review
Longboat Key, Florida
2 Bedrooms
3 Bath(s) Sleeps 4
Cedars East Townhome on beautiful Longboat Key
Condo Rental
9.8 Star Review
Longboat Key, Florida
1 Bedrooms
1 Bath(s) Sleeps 5
Renovated Beach Paradise. Ground Floor unit 64
Private Home Rental
9.6 Star Review
Longboat Key, Florida
3 Bedrooms
4 Bath(s) Sleeps 6
Steps to Beach-Full gulf views infinity pool-EXQUISITE! Ask @ seasonal specials!
Condo Rental
10.0 Star Review
Longboat Key, Florida
2 Bedrooms
2 Bath(s) Sleeps 6
Beachfront Condo
Condo Rental
9.0 Star Review
Longboat Key, Florida
2 Bedrooms
2 Bath(s) Sleeps 4
Beautiful Beachplace - 1135 Gulf of Mexico Drive
Private Home Rental
10.0 Star Review
Longboat Key, Florida
4 Bedrooms
4 Bath(s) Sleeps 8
Beach and Boaters Paradise! Heated pool, Fish off the dock, walk to the beach!
Condo Rental
Longboat Key, Florida
3 Bedrooms
2 Bath(s) Sleeps 8
Rare 3 Bedroom Condo/Villa with Beautiful Bay Views
Private Home Rental
9.4 Star Review
Longboat Key, Florida
1 Bedrooms
2 Bath(s) Sleeps 6
Longboat Key’s rare location!Beautiful canal front house with a private dock!
Condo Rental
9.6 Star Review
Longboat Key, Florida
1 Bedrooms
1 Bath(s) Sleeps 4
Wonderful Canal Front Condo on LBK! Bring Your Boat!Cabana Beach Club UNIT 11.
Private Home Rental
2.0 Star Review
Longboat Key, Florida
3 Bedrooms
2 Bath(s) Sleeps 6
Tropical Paradise - boutique house and cottage with outdoor entertainment deck
Condo Rental
10.0 Star Review
Longboat Key, Florida
2 Bedrooms
2 Bath(s) Sleeps 4
Beachplace 4-604 Luxury 2 BR/2 BA Penthouse Condo. AVAIL JAN 2026!
Private Home Rental
9.4 Star Review
Longboat Key, Florida
2 Bedrooms
2 Bath(s) Sleeps 6
2 BR Beach front villa with enclosed lanai overlooking the pool
Cottage Rental
Longboat Key, Florida
1 Bedrooms
1 Bath(s) Sleeps 4
Relax and Recharge in this 1BR Cottage
Cottage Rental
Longboat Key, Florida
3 Bedrooms
2 Bath(s) Sleeps 8
3BR Cottage- Footsteps to the Sand
Condo Rental
9.6 Star Review
Longboat Key, Florida
1 Bedrooms
1 Bath(s) Sleeps 4
Beachfront 1-bedroom condo in Longboat Key, Private beach in your backyard.
Cottage Rental
Longboat Key, Florida
4 Bedrooms
2 Bath(s) Sleeps 10
Your Home Away from Home: Little Gull 4BR Cottage
Cottage Rental
Longboat Key, Florida
2 Bedrooms
2 Bath(s) Sleeps 6
2BR Cottage Gulf Side of Property, Resort Amenities
Cottage Rental
10.0 Star Review
Longboat Key, Florida
2 Bedrooms
2 Bath(s) Sleeps 6
2BR Cottage Bayside Close to the Pool
Cottage Rental
Longboat Key, Florida
1 Bedrooms
1 Bath(s) Sleeps 4
Salt Air, Sunlight, and Old Florida Flair
Cottage Rental
Longboat Key, Florida
1 Bedrooms
1 Bath(s) Sleeps 4
1BR Gulfside Cottage Charming, Quiet, and Warmer Than Your Forecast
Cottage Rental
Longboat Key, Florida
2 Bedrooms
2 Bath(s) Sleeps 6
Longboat Key Cottage Steps to Pool and Bay Dock
Cottage Rental
Longboat Key, Florida
2 Bedrooms
2 Bath(s) Sleeps 6
2BR Cottage Bayside Time for Relaxation
Cottage Rental
Longboat Key, Florida
1 Bedrooms
1 Bath(s) Sleeps 4
Your Winter Reset: Gulf Breezes + Good Vibes
Cottage Rental
Longboat Key, Florida
1 Bedrooms
1 Bath(s) Sleeps 4
Throwback Charm Meets Beach Bliss 1BR Cottage
Cottage Rental
Longboat Key, Florida
1 Bedrooms
1 Bath(s) Sleeps 4
1BR Gulf Breezes & Old Florida Charm
Cottage Rental
Longboat Key, Florida
2 Bedrooms
2 Bath(s) Sleeps 6
2BR Cottage Bayside of Property, Full Resort Amenities
Private Home Rental
9.8 Star Review
Longboat Key, Florida
3 Bedrooms
4 Bath(s) Sleeps 10
Your Paradise Awaits...
Condo Rental
10.0 Star Review
Longboat Key, Florida
2 Bedrooms
2 Bath(s) Sleeps 6
Beach Condo with Quiet, Private Beach
Private Home Rental
10.0 Star Review
Longboat Key, Florida
4 Bedrooms
3 Bath(s) Sleeps 8
Longboat Key , Beach , Pool , Dock , Canal , Boat Access. Kayak rentals, Fishing
Condo Rental
9.6 Star Review
Longboat Key, Florida
2 Bedrooms
2 Bath(s) Sleeps 4
Can't Get Closer to the Beach Without Getting Your Feet Wet!
Condo Rental
9.6 Star Review
Longboat Key, Florida
2 Bedrooms
2 Bath(s) Sleeps 6
Breathtaking Beach Front Property Ground Floor Condo