Search Results - Vacation Rentals

Longboat Key, Florida Vacation Rentals

144 listings found
About Longboat Key, Florida

A Longboat Key vacation may be just what you and your family need to escape the hectic hustle and bustle of everyday life. Does a relaxing stay in a sumptuous Longboat Key resort or a private condo in Longboat Key sound appealing to you?  Read on to discover all the perks and amenities that Longboat Key rentals offer to you!

Rest and Relaxation in Longboat Key Vacation Rentals

Can you picture yourself kicking back and putting up your feet on the shady balcony of a Longboat Key condo rental?  How about lounging on a white sandy beach while the water washes over your toes while the kids look for seashells? All of this is available to you at Longboat Key vacation rentals and condominiums in Longboat Key. At all Longboat Key rentals you will be close to the water and the fabulous views of the beautiful Gulf of Mexico. This picturesque area of southwest Florida is full of comfortable Longboat Key condos, plush Longboat Key resorts and roomy vacation houses in Longboat Key. After a tranquil night’s sleep in your Longboat Key condo, spend a lazy morning with your fishing pole on one of the many boardwalks or piers close to Longboat Key house rentals. If you feel a bit more energetic, rent a bicycle and explore the beautiful southwest Florida landscape close to your condo in Longboat Key.  In the evening, take a short trip from your Longboat Key vacation rental to a nearby restaurant for a gourmet dinner or some entertaining island music. Finish off the evening on the deck of your vacation house in Longboat Key with your favorite tropical drink. What a great place to watch a spectacular Gulf sunset!

Fun in the Sun at Longboat Key Rentals

If you’ve had enough R & R, then it’s time to head out the door of your Longboat Key house rental and investigate what else the area has to offer! From golf tournaments to triathalons to the annual Longboat Key Chalk on the Walk festival, you will never lack for things to do on a Longboat Key vacation!  Near Longboat Key condo rentals is the Ringling Museum of Art, founded by the famous Ringling circus family. The museum features beautiful gardens, art collections and of course, a circus museum!  Just a few miles away from Longboat Key resorts and condos in Longboat Key is the bustling city of Sarasota, home to unique shops, museums and sports teams. There you and your family can hop on a charter boat and tour the beautiful barrier islands of the southwest Florida.  Play a little putt-putt, or if you are a more serious golfer, there are many championship golf courses close to Longboat Key house rentals. Longboat Key condos are also a great place to stay if you want to visit the Sarasota Classic Car Museum.  Whatever your interests, you can find many things to entertain you when you stay at a Longboat Key condo rental!

How could you not find a vacation in Longboat Key appealing? In Longboat Key you will have the best of both worlds, a secluded quiet island where you can relax and, close by, bigger cities and islands that have the best restaurants and sightseeing in southwest Florida. How could you go wrong with a Longboat Key rental? Pack your bags and buy your tickets for a vacation you and your family will remember for a lifetime!

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Rate & Availability Disclaimer
Base rates (EXCLUDING any applicable taxes, fees, and promotions) are displayed as provided by rental managers and are not guaranteed. Rates are based on the start date or arrival date selected in the search and may vary on subsequent days. Properties marked ‘Available’ or ‘Booked’ are done so based on information provided by the rental manager and are not guaranteed. For completed details (including minimum stay length, full availability information, approved arrival days and other booking rules for the property) select ‘Book Now” (on available properties) or ‘Check Availability’ (booked properties) to be directed to the rental manager’s website or click “Contact” to send them a specific request.

Sunset Heaven | St Armands - Lido Key Home w/ Water Views, Dock Access, Private Heated Pool & Spa!

New Listing! Manatee Cove | Waterfront Home on Lido Key, 30 Second Walk to St. Armands Circle!

Coconut Cottage | Home on Lido Key w/ Private Heated Pool/Spa, Walk to Lido Beach & St. Armands!

New Listing! Mermaids Oasis | Private Pool, 5 Minute Walk to St. Armands Circle!

New Listing! | Front Row Seat | Luxury Beachfront Home Located On Anna Maria Island!

New Listing! | Beach a la Mode | Luxury Canal Front Home on Anna Maria Island!

Palm Paradise | Pet Friendly Home on Siesta Key w/ Large Heated Private Pool & Outdoor Area!

Floritas Key | Pet Friendly Home on Siesta Key w/ Large Heated Private Pool & Outdoor Area!

Bay Isle Bliss | Pet Friendly Home w/ Private Pool & Walking Distance to Shell Beach

Hemingway House | Beautiful Traditional Home w/ Spacious Outdoor Dining Area & Lush Landscaping

Casa Leone | Pet Friendly Home on Siesta Key w/ Private Heated Pool & Putting Green!

Baydream Bungalow | Pet Friendly Home w/ Private Heated Screened-In Pool

New Listing! Siesta Dolce | Luxury Siesta Key Home w/ Private Heated Pool, Close To Beach!

The Pearl on the Bay | Luxury Water Front Home Near Siesta Key, Gorgeous Views & Private Pool!

Coral Breeze | Siesta Home, Heated Pool & Spa, Minutes to Village and Beach!

New Listing! Island Sol | Private Pool, Pet Friendly, Minutes from Siesta Beach

New Listing! Sunburst Courtyard | Pet Friendly Waterfront Home, Walk to Siesta Key Beach & Village!

Casamigos | West of the Trail - Private Home with Tiki Bar, Heated Pool, and Spa, Near Siesta Key!

Ventana Rosa | Beautiful Sarasota Home Near Siesta Key w/ Private Pool & Large Outdoor Space

Ocean Sky | Pet Friendly Home in Sarasota w/ Private Heated Pool & Fire Pit!

Villa De Paradisio | Waterfront Home w/ Private Pool, Fishing Dock, Close to Beach & Village!

Hidden Treasure | Located on Siesta Key w/ Private Heated Pool/Hot Tub & Spacious Outdoor Area

Blu Sky Cottage | Pet Friendly, Canal Front Home on Siesta Key w/ Private Heated Pool & Spa, Kayaks!

Sea Foam | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

Sea Angel | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

Sea Breeze | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

Sea Coast | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

The Beachy Keen | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

CJs on Siesta | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

The Coral Reef! | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

Sea Escape | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

Sea Dream | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

Tropical Oasis | Luxury Home on Siesta Key w/ Private Heated Pool/ Spa, Steps to Beach & Village!

Villa Castile | Pet Friendly Home on Siesta Key w/ Private Heated Pool, Walk to Beach & Village!

Bali Hai House | Luxury Waterfront Home on Siesta Key w/ Large Private Heated Pool & Outdoor Patio!

Casa De Siesta | Pet Friendly Home In Siesta Village, Private Pool and Hot Tub, Walk to the Beach!

Villa Margarita | Pet Friendly Home In Siesta Village, Heated Pool and Hot Tub, Walk to the Beach!

Villa Fiesta | Pet Friendly Home In Siesta Village, Heated Pool and Hot Tub, Walk to the Beach!

Siesta Soul | Multilevel Home Located in Siesta Key Village w/ Private Pool, Fire Pit, Walk to Beach

The Big Kahuna | Luxury Pet Friendly Home on Siesta Key, 2 Heated Pools, Steps to Beach & Village!

Casa Mahalo | Pet Friendly Home on Siesta Key w/ Private Heated Pool, Steps to Beach & Village!

Casa Ohana | Pet Friendly Home on Siesta Key w/ Private Heated Pool, Steps to Beach & Village!

Vinca | Pet Friendly Home Located in Siesta Key Village w/ Heated Pool, Walk to Beach!

Honeysuckle | Pet Friendly Home Located in Siesta Key Village w/ Heated Pool, Walk to Beach!

Mandevilla | Pet Friendly Home Located in Siesta Key Village w/ Heated Pool, Walk to Beach!

Plumbago | Pet Friendly Home Located in Siesta Key Village w/ Heated Pool, Walk to Beach!

Lantana | Pet Friendly Home Located in Siesta Key Village w/ Heated Pool, Walk to Beach!

Mimosa | Pet Friendly Home Located in Siesta Key Village w/ Heated Pool, Walk to Beach!

The Hummingbird | Pet Friendly Home Located in Siesta Key Village w/ Private Pool, Walk to Beach!

Siesta Breeze Retreat | Walk to Beach, Siesta Village, Shared Pool!

At Sun Sea Terrace | Luxury Siesta Key Condo w/ Heated Pool, Short Walk to Beach and Village!

Siesta Villa | Luxury Condo in Siesta Village w/ Heated Pool, Walking Distance to Beach & Village!

Luna Nueva | Pet Friendly Home in Sarasota w/ Private Heated Pool & Screened-In Porch

Luna Flores | Pet Friendly Home in Sarasota w/ 2 Private Heated Pools & Screened-In Porches

Villa Las Flores | Pet Friendly Home in Sarasota w/ Private Heated Pool & Screened-In Porch

Caribbean Dream | Luxury Condo on Siesta Key w/ Heated Pool, Walking Distance to Beach & Village!

New Listing! The Birdhouse | Private Siesta Key Home w/ Heated Pool, Minutes Away From Beach!

New Listing | Pet Friendly Home on Siesta Key w/ Outdoor Patio & Private Screened-In Heated Pool!

The Palms Cottage | Pet Friendly Home w/ Private Pool & Spa, Walking Distance to Siesta Key Beach!

Sea la Vie | Walking Distance to Siesta Key Beach & Village w/ Heated Pool & Outdoor Dining

Sea Esta | Walking Distance to Siesta Key Beach & Village w/ Heated Pool & Outdoor Dining

Siesta Salt Life | Walking Distance to Siesta Key Beach & Village w/ Private Heated Pool!

The Key Canal - Spacious Waterfront Home w/ Rooftop Deck, Walk to Siesta Beach & Village

Latitude Adjustment | Waterfront Home w/ Private Heated Pool! Walk to Siesta Village & Beach!

Villa Champagne | Pet Friendly Waterfront Home w/ Private Pool & Spa, Close to Beach & Village!

Sophie's Quartier | Siesta Bundle, 2 Pet Friendly Waterfront Homes w/ 2 Private Pools, Near Village

Sophie's Cottage | Pet Friendly, Waterfront Home w/ Private Pool & Kayaks! Beach & Village Close!

Isla Amor | Waterfront Home on Siesta Key w/ Private Heated Pool, Fire Pit, Walk to Beach!

Beach Walk Cottage | Pet Friendly Home on Palm Island, Private Pool, Ping Pong Table, Walk to Beach!

Seas the Day | Canal Front Home on Siesta Key w/ Private Heated Pool & Kayaks, Walk to Beach!

Endless Views | Walking Distance To Siesta Key Beach + Village, Panoramic Views

New Listing! Avanti Villa | Hot Tub, Walk to Siesta Beach and Village, Beach Views

Siesta Sunset | Luxurious Beach Front Penthouse w/ Views of Gulf, Minutes to Siesta Key Village

Seaside Cottage | Pet Friendly Siesta Key Home w/ Private Pool, Across From Beach Access 9!

New Listing! Don't Be Salty | Gorgeous Modern Home w/ Private Heated Pool & Spa, Near Beach!

The Sun Dial | Waterfront Home on Siesta Key w/ Private Pool & Large Backyard, Close to Beach!

Monarch Villa | Ocean Views, Cabana Room, Heated Pool, & Steps to Siesta Key Beach!

Peacock Villa | Spacious Outdoor Area, Cabana Room, Heated Pool, & Steps to Siesta Key Beach!

Casa De Mariposa | Ocean Views, Spacious Balcony, Private Heated Pool, & Steps to Siesta Key Beach!

Island Escape | Home on Siesta Key w/ Private Heated Pool & Ping Pong Table!

Beach Dream | Home w/ Ocean Views, 2 Private Pools, & Rooftop Lookout! Steps to Siesta Key Beach

Silver Shore | Home w/ Ocean Views, Private Pool, & Rooftop Lookout! Steps to Siesta Key Beach

Crystal Sands | Home w/ Ocean Views, Private Pool, & Rooftop Lookout! Steps to Siesta Key Beach

Beach Palm Villa | Private Heated Pool, Fire Pit, & Spacious Outdoor Lounging Area

Sand Dollar Cottage | Waterfront Home w/ Private Pool & Kayaks! Minutes to Siesta Key Beach!

Admirals Watch | Ocean View w/ Spacious Balcony, Heated Pool, & Walking Distance to Siesta Key Beach

Villa Vista Mare | Gorgeous Home w/ Views of Gulf, Heated Pool, & Across From Siesta Key Beach!

La Contento Casa | Pet Friendly, Waterfront Home on Siesta Key w/ Private Heated Pool & Kayaks!

New Listing | Gulf Birdie | Waterfront Home on Siesta Key, w/ Private Heated Pool & Hot Tub!

Sandpiper Cottage | Pet Friendly Home in Sarasota w/ Private Pool, 2 Story Loft, Close to Siesta Key

The Nautilus | Luxury Pet Friendly Home on Siesta Key, 2 Heated Pools, 2 Elevators, Steps to Beach!

Casa Tegula | Pet Friendly Home on Siesta Key w/ Private Heated Pool & Elevator, Steps to Beach!

Casa Stolida | Pet Friendly Home on Siesta Key w/ Private Heated Pool & Elevator, Steps to Beach!

Casa Junonia | Pet Friendly Home on Siesta Key w/ Private Heated Pool & Elevator, Steps to Beach!

The Abalone | Luxury Pet Friendly Home on Siesta Key, 2 Heated Pools, 2 Elevators, Steps to Beach!

Casa Eulimia | Pet Friendly Home on Siesta Key w/ Private Heated Pool & Elevator, Steps to Beach!

Casa Bella Vita | Luxury Home w/ Heated Pool, Ping Pong Table, & Walking Distance to Crescent Beach!

The Conch | Luxury Pet Friendly Home on Siesta Key, 2 Heated Pools, 2 Elevators, Steps to Beach!

Casa Antilles | Pet Friendly Home on Siesta Key w/ Private Heated Pool & Elevator, Steps to Beach!

Casa Coquina | Pet Friendly Home on Siesta Key w/ Private Heated Pool & Elevator, Steps to Beach!

Topsail Cottage | Luxury Home on Siesta Key w/ Heated Pool & Rooftop View of Gulf, Walk to Beach!

Fiesta Playa | Luxury Home on Siesta Key w/ Private Elevator, 2 Minute Walk to Crescent Beach!

Serenity Cottage | Multilevel Home on Siesta Key w/ Private Pool & Spa, Short Walk to Beach!

Crescent Cottage | Private Pool, Lounging Area, Short Walk to Crescent Beach

Sandy Seahorse Cottage | Pet Friendly Home on Siesta Key w/ Private Pool, Short Walk to Beach

Sandy Rocks | Ultimate Bundle: 2 Private Pet Friendly Homes, 2 Private Heated Pools, Walk to Beach!

Sandy Cabana | Pet Friendly Home on Siesta Key w/ Heated Pool, Short Walk to Beach!

Seahorse Cabana | Pet Friendly Home on Siesta Key w/ Heated Pool, Short Walk to Beach!

Casita Morning Star | Pet Friendly Home on Siesta Key, Heated Pool, Walk to Beach & South Village!

The Solaster | Pet Friendly Home on Siesta Key w/ 2 Heated Pools, Walk to Beach & South Village!

Casita Sun Star | Pet Friendly Home on Siesta Key, Heated Pool, Walk to Beach & South Village!

Turtle Bay Hideaway | Large Pet Friendly Home on Siesta Key w/ Private Pool & Spa, Beach Access

Florida Retreat Nr Lakewood Ranch Sports Campus

Cozy 2BR Florida Home Near the Shore!

King Bed & Patio, Minutes to the Beach

Venice Villas * Villa Paradiso #18

Venice Villas * Villa Paradiso #14

Venice Villas * Villa Laguna #28

Venice Villas * Studio #69

Venice Villas * Poolside #41

Venice Villas * Villa San Marco #33

Venice Villas * Studio #74

Venice Villas * Villa San Marco #31

Venice Villas * Villa Regina #1

Venice Villas * Villa San Marco #34

Venice Villas * Villa San Marco #37

Venice Villas * Villa San Marco #38

Venice Villas * Studio #49

Venice Villas * Villa Paradiso #12

Venice Villas * Unit #45

Venice Villas * Villa Paradiso #13

Venice Villas * Studio #76

Venice Villas * Studio #51

Venice Villas * Villa Regina #6

Venice Villas * Villa San Marco #32

Venice Villas * Villa Laguna #27

Venice Villas * Villa Regina #5

Venice Villas * Studio #78

Venice Villas * Studio #58

Venice Villas * Studio #53

Venice Villas * Studio #61

New centrally located chic family home in Tampa

TampaGolfVillas by AmericanVacationLiving 7 Room

TampaGolfVillas by AmericanVacationLiving 5 Room