Vacation Rentals in Longboat Key, Sarasota

Apartment Rental 5.0 Star Review

Longboat Key, Florida
2 Bedrooms 2 Bath(s) Sleeps 6

Sea Grape Inn #5- BEACHFRONT Property

Apartment Rental 4.7 Star Review

Longboat Key, Florida
2 Bedrooms 2 Bath(s) Sleeps 4

Sea Grape Inn #4- BEACHFRONT Property

Apartment Rental 4.9 Star Review

Longboat Key, Florida
2 Bedrooms 2 Bath(s) Sleeps 6

Sea Grape Inn #7 - BEACHFRONT Property

Private Home Rental 4.5 Star Review

Longboat Key, Florida
2 Bedrooms 2 Bath(s) Sleeps 7

Longboat key paradise townhome with an attached double deep garage.

Condo Rental

Longboat Key, Florida
2 Bedrooms 2 Bath(s) Sleeps 6

Luxury Condo located on Beachfront Property

Condo Rental 5.0 Star Review

Longboat Key, Florida
2 Bedrooms 4 Bath(s) Sleeps 5

LBK Getaway

Condo Rental 4.9 Star Review

Longboat Key, Florida
2 Bedrooms 2 Bath(s) Sleeps 6

May 2023 available. On the beach, Sun set and Sunrise view, Monthly rental

Condo Rental 5.0 Star Review

Longboat Key, Florida
1 Bedrooms 1 Bath(s) Sleeps 2

Whitney Beach Gulfside With Balcony! 30 day lease but real occupancy negotiable.

Condo Rental

Longboat Key, Florida
2 Bedrooms 2 Bath(s) Sleeps 4

Stunning 2 BR Condo views of the Gulf and Lake

Villa Rental 5.0 Star Review

Longboat Key, Florida
2 Bedrooms 1 Bath(s) Sleeps 4

Spectacular 5-star Condo. Walk to beach & restaurants. Just remodeled.

Condo Rental 4.5 Star Review

Longboat Key, Florida
1 Bedrooms 1 Bath(s) Sleeps 4

Gulf Getaway with Porch + Direct Beach Access!

Condo Rental 5.0 Star Review

Longboat Key, Florida
2 Bedrooms 2 Bath(s) Sleeps 6

1st Floor Home Away from Home - Steps to Beach - Pool

Cottage Rental 5.0 Star Review

Longboat key, Florida
1 Bedrooms 1 Bath(s) Sleeps 4

Bikini Bottom Cottage in the historic village of Longboat Key

Cottage Rental 4.6 Star Review

Longboat Key, Florida
2 Bedrooms 1 Bath(s) Sleeps 6

A Beach Front Cottage: Beautiful & Private: Weekly or Monthly.

Condo Rental 4.8 Star Review

Longboat Key, Florida
2 Bedrooms 2 Bath(s) Sleeps 6

Updated Beach Style Condo at Sand Cay with Great Ocean Views.

Condo Rental 5.0 Star Review

Longboat Key, Florida
2 Bedrooms 2 Bath(s) Sleeps 4

Million Dollar View!

Condo Rental 4.8 Star Review

Longboat Key, Florida
2 Bedrooms 2 Bath(s) Sleeps 4

2 bedroom beachfront condo by FVC

Condo Rental

Longboat Key, Florida
2 Bedrooms 2 Bath(s) Sleeps 4

Beautiful Longboat Key Condo Surrounded by Ocean

Hotel resort Rental 5.0 Star Review

Longboat Key, Florida
2 Bedrooms 2 Bath(s) Sleeps 6

Florida's Longboat Key Paradise

Apartment Rental

Longboat Key, Florida
Studio 1 Bath(s) Sleeps 2

Beautiful Studio apartment (426643) by Houzlet

Private Home Rental 5.0 Star Review

Longboat Key, Florida
3 Bedrooms 2 Bath(s) Sleeps 6

PARADISE FOUND#PEACEFUL & ELEGANT UPDATED#CANAL HOME#WALK TO BEACH#NEWER BIKES

Condo Rental 4.9 Star Review

Longboat Key, Florida
2 Bedrooms 1 Bath(s) Sleeps 6

Gorgeous condo on the beautiful Longboat Key beach

Condo Rental 4.8 Star Review

Longboat Key, Florida
2 Bedrooms 2 Bath(s) Sleeps 6

GULF FRONT CONDO / PRIVATE PATIO / STEPS TO THE BEACH

Condo Rental

Longboat Key, Florida
2 Bedrooms 2 Bath(s) Sleeps 4

Welcome to your Beach Front Dream Condo!! LBKTP102

Private Home Rental 4.0 Star Review

Longboat Key, Florida
2 Bedrooms 2 Bath(s) Sleeps 4

Peaceful Longboat Key Canal Home

Condo Rental 4.0 Star Review

Longboat Key, Florida
2 Bedrooms 2 Bath(s) Sleeps 4

Fall dates available! Call for your getaway.

Private Home Rental

Longboat Key, Florida
6 Bedrooms 6 Bath(s) Sleeps 10

LUXURY VACATION HOME--6 BDRM w 8 BEDS--Steps Away to Private Beach--PET FRIENDLY

Condo Rental 5.0 Star Review

Longboat Key, Florida
2 Bedrooms 2 Bath(s) Sleeps 4

BEAUTIFUL VIEWS OF THE BAY! THIS IS AN AMAZING 2/2! December dates still available!

Condo Rental

Longboat Key, Florida
2 Bedrooms 2 Bath(s) Sleeps 6

Silver Sands, Oceanfront - Gulf Beach Resort

Condo Rental

Longboat Key, Florida
2 Bedrooms 2 Bath(s) Sleeps 4

Gorgeous Beachside Condo in superior Longboat Location

Private Home Rental

Longboat Key, Florida
4 Bedrooms 5 Bath(s) Sleeps 10

Luxury 4 brm home by FVC

Private Home Rental

Longboat Key, Florida
1 Bedrooms 1 Bath(s) Sleeps 3

Gulf Beach Resort - A

Private Home Rental

Longboat Key, Florida
1 Bedrooms 1 Bath(s) Sleeps 3

Gulf Beach Resort - B

Condo Rental 4.7 Star Review

Longboat Key, Florida
1 Bedrooms 1 Bath(s) Sleeps 4

Longboat Key Club!! Direct Beachfront!!

Private Home Rental

Longboat Key, Florida
2 Bedrooms 1 Bath(s) Sleeps 6

Starfish Bungalow A. Steps to the beach 2/1 Coastal paradise ! Large airy open layout, grill, wifi !

Private Home Rental 5.0 Star Review

Longboat Key, Florida
2 Bedrooms 1 Bath(s) Sleeps 6

Canal front cottage, walking distance to sandy Gulf

Condo Rental 4.4 Star Review

Longboat Key, Florida
2 Bedrooms 2 Bath(s) Sleeps 6

Unit #207 Sand Cay Beach Resort Pool and Garden View

Cottage Rental 5.0 Star Review

LongBoat Key, Florida
3 Bedrooms 2 Bath(s) Sleeps 8

FANTASTIC COTTAGE ON LONG BOAT KEY FLORIDA...WEEK OF March 30- April 6 2024

Private Home Rental 4.9 Star Review

Longboat Key, Florida
4 Bedrooms 4 Bath(s) Sleeps 8

Hidden Bay/Beach Paradise

Condo Rental

Longboat Key, Florida
1 Bedrooms 1 Bath(s) Sleeps 4

Waterfront condo with Gulf views, pool, tennis, & deeded beach access

Condo Rental 4.8 Star Review

Longboat Key, Florida
2 Bedrooms 2 Bath(s) Sleeps 6

Tasteful 2brm Beachfront luxury

Condo Rental 4.9 Star Review

Longboat Key, Florida
2 Bedrooms 2 Bath(s) Sleeps 4

Bird's eye beach view by FVC

Condo Rental 4.7 Star Review

Longboat Key, Florida
2 Bedrooms 2 Bath(s) Sleeps 6

Unit #212 Sand Cay Beach Resort Pool and Garden View

Condo Rental 4.9 Star Review

Longboat Key, Florida
2 Bedrooms 2 Bath(s) Sleeps 6

Unit #211 Sand Cay Beach Resort Pool and Garden View

Condo Rental 4.8 Star Review

Longboat Key, Florida
2 Bedrooms 2 Bath(s) Sleeps 4

Amazing 2/2 Condo LBK w/ Spectacular Bay Views!

Condo Rental 5.0 Star Review

Longboat Key, Florida
2 Bedrooms 2 Bath(s) Sleeps 4

PENTHOUSE w/full ocean & bay views from every room

Condo Rental 4.8 Star Review

Longboat Key, Florida
Studio 1 Bath(s) Sleeps 3

*** OCEAN FRONT STUDIO SPECIAL *** FROM $99/NIGHT

Condo Rental 5.0 Star Review

Longboat Key, Florida
1 Bedrooms 1 Bath(s) Sleeps 4

Beachcomber unit 205

Private Home Rental 5.0 Star Review

Longboat Key, Florida
3 Bedrooms 3 Bath(s) Sleeps 6

Modern Bayfront Retreat with boat dock and short walk to Beach

Apartment Rental 4.9 Star Review

Longboat Key, Florida
2 Bedrooms 2 Bath(s) Sleeps 6

Sea Grape Inn #1- BEACHFRONT Property

Condo Rental 4.7 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 4.8 Star Review

Longboat Key, Florida
1 Bedrooms 1 Bath(s) Sleeps 6

Gulf Front 1 BR with Great Room Awesome View End Unit 227 with 42' TV

Condo Rental 4.9 Star Review

Longboat Key, Florida
2 Bedrooms 2 Bath(s) Sleeps 6

On the beach! Contemporary condo, 2 BR/BA, heated pool, tennis

Apartment Rental

Longboat Key, Florida
1 Bedrooms 1 Bath(s) Sleeps 2

1 Bedroom Single_family (94553) by Houzlet

Apartment Rental 4.7 Star Review

Longboat Key, Florida
Studio 1 Bath(s) Sleeps 2

Luxurious Beachfront Suite by FVC

Private Home Rental

Longboat Key, Florida
3 Bedrooms 2 Bath(s) Sleeps 6

Boaters dream! Deep water canal on Buttonwood Harbour LBK

Condo Rental

Longboat Key, Florida
2 Bedrooms 2 Bath(s) Sleeps 4

2 Bedroom Condo (20868) by Houzlet

Private Home Rental 4.9 Star Review

Longboat Key, Florida
4 Bedrooms 4 Bath(s) Sleeps 10

Private Island Retreat with Private Beach, Dock, Palm Trees & Glorious Sunsets

Hotel resort Rental

Longboat Key, Florida
1 Bedrooms 1 Bath(s) Sleeps 4

Not Currently Available

Condo Rental 5.0 Star Review

Longboat Key, Florida
Studio 1 Bath(s) Sleeps 3

*** OCEAN FRONT STUDIO SPECIAL *** FROM $99/NIGHT