Home Vacation Rentals By Owner In Longboat Key, FL

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$319.64

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Cottage

1BR Gulf Breezes & Old Florida Charm

Longboat Key, Florida, United States

Kick off your shoes and settle into the easy rhythm of coastal living. Start your mornings with a stroll along the soft sands, spend the afternoon exploring the island or lounging in the sun, and wrap it all up with a front-row seat to one of Longboat Key’s legendary Gulf sunsets—drink in hand, sea breeze in your hair, and not a care in the world.brbrThis charming Cape Cod-style cottage blends cozy comfort with classic beach style, making it the perfect retreat for couples, families, or small groups.brbrInside the Cottage:brPrimary Bedroombr• King-size bed for a restful night’s sleepbrbrLiving Roombr• Queen sleeper sofabr• Fireplace for a cozy touch on cooler nightsbr• Plenty of space to relax, read, or playbrbrKitchenbr• Galley-style with full-sized appliancesbr• Stocked with all the basics—just add groceries and good companybrbrWildlife, Waves & That Old-Florida MagicbrLongboat Key is teeming with natural beauty. Don’t be surprised if you spot wild parrots overhead, a tortoise crossing your path, or one of the island’s famous peacocks showing off. The cottage’s relaxed vibe fits right in with the local charm and lush surroundings.brbrGood to Know:br• Stairs required to access this cottagebr• No pets, no smoking or vaping, and no partiesbr• Must be 21+ to rent and check inbr• Refundable security hold required at check-in (see details)br• While we aim to keep all amenities in great shape, maintenance may occur—we resolve issues quickly and professionally.brbrOnsite Office Hours:br• Monday–Friday: 8 AM – 4 PMbr• Saturday: 9 AM – 5 PMbrbrThis is your invitation to slow down, breathe deep, and enjoy the simple pleasures of the Gulf. Your beachside cottage is waiting.
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$629.32

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Cottage

Little Gull 2BR Cottage with Ultimate Views of the Famous Sunsets

Longboat Key, Florida, United States

Step back in time and settle into a slice of Old Florida at Little Gull Cottage, a 2-bedroom, 2-bath coastal retreat that blends beachy charm with modern comfort. Perched above the shoreline (yes, there are stairs—but the view is worth every step), this Gulf-front gem offers a front-row seat to Longboat Key’s natural magic: think wild parrots, graceful egrets, slow-moving tortoises, and if you’re lucky, a peacock strutting by in full fanfare.brbrInside the Cottage:brPrimary Bedroom:br• King bedbr• Private ensuite bathbrbrGuest Bedroom:br• Two Twin BedsbrbrLiving Room:br• Queen sofa bed for extra guestsbr• Fireplace, comfy seating, and the perfect vibe for evening chats or rainy-day card gamesbrbrKitchen:br• Full kitchen with basic essentials for simple meals or your morning brew ritualbr• Enjoy your coffee on the private porch, with one of the best views in the resortbrbrWhat to Know:br• Stairs are required to reach the cottage—pack light and wear comfy shoesbr• No pets, no smoking or vaping, no partiesbr• Must be 21+ to rent and check inbr• Security deposit hold required at check-in (fully refundable after inspection)br• Occasionally, maintenance happens—we strive to handle it quickly and with carebrbrOffice Hours:br• Monday–Friday: 8 AM–4 PMbr• Saturday: 9 AM–5 PMbrbrIf you’re craving that throwback beach vacation—sand between your toes, wildlife out your window, and a cozy cottage to call your own—Little Gull is calling. Come find out why Longboat Key is the Florida you didn’t know you were missing.
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Bath 2

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Sleep 6

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Exceptional(16)

$290.04

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Condo

Luxurious Beachfront Villa with Private Pool

Longboat Key, Florida, United States

This three-bedroom, three-bathroom unit is 2,200 square feet and steps from the Gulf of Mexico. Guests will enjoy a secluded beach, heated community pool, private balconies, community hot tub and secure access. The unit is recently renovated and located across the street from a public park, a convenience store, two restaurants and a bicycle shop. The Villas of Avignon is an eight-unit complex is less than ten miles from shopping, dining, and entertainment of St. Armand's Circle and less than 15 miles from downtown Sarasota.
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Sleep 8

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$143.12

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Condo

BEACHFRONT VACATION RENTAL WITH FULL GULF VIEWS!

Longboat Key, Florida, United States

Spectacular Gulf views of the beach and sunsets from this updated and spacious 5th floor 2-bedroom, 2-bath turnkey furnished condo at The Arbormar, located mid-island on Longboat Key and close to restuarants and shoppiing. Open balcony looks directly onto the beach with water views from living and dining room. Flat screen smart cable TV and FREE WiFi Internet access in living room and bedrooms. Pull-out couch in living room. Fully equipped and spacious kitchen with plenty of cabinet and storage space. Master bedroom has king bed with master bath en-suite and walk-in shower, and built-in closet storage space. Guest bedroom has twin beds and guest bath is tub/shower. Shared coin-operated washer/dryer (only 4 units/floor) immediately outside unit. This unit is fully furnished - - just bring food and clothes!brbrArbormar offers many fine amenities including assigned covered parking, heated swimming pool, golf putting green beach-side and shuffleboard with picnic area, BBQ grill and kayak storage. The 1st floor clubroom offers catering kitchen and spacious seating for parties and groups. There is a fitness center overlooking the Gulf, sauna with shower and restrooms directly off the pool. Enjoy spectacular Gulf views in this tropical paradise setting on Longboat Key.brbrContact Wagner Realty for pricing and availablity *****brbrAmenities Include:brbr- View: Full Gulfbrbr- Application Fee Req.: $100brbr- Waterfront: Yesbrbr- Beach Distance: on the beachbrbr- Pool, Heated: heated poolbrbr- Beach Access: deededbrbr- Pool: communitybrbr- TV Cable/Satellite: cable TVbrbr- Internet Access: WiFi Internet accessbrbr- washer dryer: Sharedbrbr- Bed Size 1st/Master: Kingbrbr- Bed Size 2nd Rm: Twinsbrbr- Beds Pull-out: Pull out couchbrbr- Elevator: Yesbrbr- Balcony: Balconybrbr- TVs/VCR/DVD: Flat screen TVsbrbr- Furnished: Turnkeybrbr- Master Bath Features: En-suitebrbr- Walk-In Shower: Yesbrbr- Garage: Carportbrbr- Activities: Pool-fitness-saunabrbr- Minimum Stay: 30 nightsbrbr- Agent: Gregory Kossbrbr- Office: Longboat Key
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Home Most popular vacation rentals in Longboat Key

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$747.69

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Private vacation home

Longboat Key home on the canal and a 5 minute walk to the beach

Longboat Key, Florida, United States

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Bath 3

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Sleep 8

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$2112.85

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Condo

Luxury Beachfront Living - St Regis Waterfront Residency - Longboat Key - Sunset Reflections

Longboat Key, Florida, United States

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Bath 2

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Sleep 5

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$1196.70

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Condo

Renovated Beachfront 2 Bedroom Condo by FVC

Longboat Key, Florida, United States

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Bath 2

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Sleep 6

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$1148.84

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Condo

Beach Front Condo on Gulf of Mexico

Longboat Key, Florida, United States

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Bath 2

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Sleep 4

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$1024.99

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Private vacation home

Sleepy Lagoon 4+bd/3.5ba canal home, 5 min walk to beach on LBK

Longboat Key, Florida, United States

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Bath 3

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Sleep 11

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$884.08

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Private vacation home

Hidden Bay/Beach Paradise

Longboat Key, Florida, United States

Bed 4

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Bath 3

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Sleep 8

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$861.14

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Condo

3 BEDROOM DIRECT OCEAN VIEW, WALKOUT TO THE BEACH!

Longboat Key, Florida, United States

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Bath 2

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Sleep 6

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$767.89

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Condo

Beachfront 4th floor 4BR Longboat Key Condo With Stunning Gulf Views Paradise Sur Mer

Longboat Key, Florida, United States

Bed 4

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Bath 4

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Sleep 8

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$755.36

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Condo

LaPlaya 204D-Beach-lovers paradise! 200 feet of private beach along the turquoise Gulf of Mexico.

Longboat Key, Florida, United States

Bed 3

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Bath 2

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Sleep 6

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$670.46

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Condo

Longboat Key Luxury Condo - walking to St. Armand's Circle!

Longboat Key, Florida, United States

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Bath 1

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Sleep 4

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