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Longboat Key Rentals

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  • Beach place in Longboat Key.
    From $167 per night (USD)

    VRBO

    Beach place in Longboat Key.

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to your dream getaway! Our beautifully appointed 2-bedroom, 2- bath condo offers the perfect balance of comfort, ...

    From $167 per night (USD)

    VRBO

    Details
  • Ground floor 2/2! Glass Lanai! Sleeps 5!
    From $314 per night (USD)

    Expedia

    Ground floor 2/2! Glass Lanai! Sleeps 5!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Enjoy all Longboat Key has to offer from Harbor Villa Club! Beautiful 2/2 directly on the bay! Gorgeous views off the pa ...

    From $314 per night (USD)

    Expedia

    Details
  • Beachplace 9-302 by FGC
    From $312 per night (USD)

    VRBO

    Beachplace 9-302 by FGC

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Beachfront renting at its finest: relax, unwind, and enjoy the magnificent views of the pristine white sandy beach and t ...

    From $312 per night (USD)

    VRBO

    Details
  • Sunset and Beach view unit 402
    From $319 per night (USD)

    Expedia

    Sunset and Beach view unit 402

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    6

    There are no ratings and reviews because this is my new property. However, I am a Premier Host with a 5-star rating and ...

    From $319 per night (USD)

    Expedia

    Details
  • Suzie's Beach House, Longboat Key
    From $264 per night (USD)

    VRBO

    Suzie's Beach House, Longboat Key

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Located in Country Club Shores close to St. Armands Circle and downtown Sarasota, this quiet, three bedroom home offers ...

    From $264 per night (USD)

    VRBO

    Details
  • Beach and Tennis Paradise in Beautiful Longboat Key
    From $267 per night (USD)

    Expedia

    Beach and Tennis Paradise in Beautiful Longboat Key

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Consider this condo directly on the beach your home away from home while you visit beautiful Longboat Key. This property ...

    From $267 per night (USD)

    Expedia

    Details
  • Grand Bay 626 by FVC
    From $216 per night (USD)

    VRBO

    Grand Bay 626 by FVC

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Luxury Waterfront Retreat at Grand Bay – Unit 626, Longboat Key Experience the ultimate in coastal elegance at this s ...

    From $216 per night (USD)

    VRBO

    Details
  • Beachplace 6-205 by FVC
    From $291 per night (USD)

    Expedia

    Beachplace 6-205 by FVC

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Beachplace 3-Bedroom Condo – Longboat Key Welcome to your perfect Florida retreat at Beachplace on Longboat Key! Prof ...

    From $291 per night (USD)

    Expedia

    Details
  • Stunning Beachfront, Gulf-to-Bay Views, 3 Bedroom Corner Condo, 2000 sq ft
    From $419 per night (USD)

    VRBO

    Stunning Beachfront, Gulf-to-Bay Views, 3 Bedroom Corner Condo, 2000 sq ft

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    This fabulous, 2000-square-foot, fourth story, corner, direct beachfront, condominium features spectacular views of the ...

    From $419 per night (USD)

    VRBO

    Details
  • 2-bedroom condo in welcoming Longboat Key with AC, WiFi
    From $318 per night (USD)

    VRBO

    2-bedroom condo in welcoming Longboat Key with AC, WiFi

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    This 2-bedroom condo is perfect for your escape to Longboat Key. The enchanting space features 1 king bed, 1 queen bed, ...

    From $318 per night (USD)

    VRBO

    Details
  • Gorgeous 2 Bedroom 2 Bath Fairway Bay Condo located in Bay Isles on Longboat Key
    From $227 per night (USD)

    VRBO

    Gorgeous 2 Bedroom 2 Bath Fairway Bay Condo located in Bay Isles on Longboat Key

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    A completely renovated newly furnished 2 bedrooms . 2 bath condo located at Fairway Bay in the Bay Isles Community. Thi ...

    From $227 per night (USD)

    VRBO

    Details
  • Breathtaking New 4 Bed/3 Bath Pool Home
    From $769 per night (USD)

    VRBO

    Breathtaking New 4 Bed/3 Bath Pool Home

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Looking for a 3 month renter for January, February, and March or atleast January 2026. Limetree House. This fabulous new ...

    From $769 per night (USD)

    VRBO

    Details
  • A Lush + Tropical Beachside Sanctuary\n2BR/2BA Condo w/ Fully Equipped Kitchen
    From $505 per night (USD)

    VRBO

    A Lush + Tropical Beachside Sanctuary\n2BR/2BA Condo w/ Fully Equipped Kitchen

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Escape to your peaceful beachside + tropical retreat, nestled in desirable South Longboat Key on 31 acres of private bea ...

    From $505 per night (USD)

    VRBO

    Details
  • Gorgeous townhouse in desirable Cedar's East Tennis Resort!
    From $372 per night (USD)

    VRBO

    Gorgeous townhouse in desirable Cedar's East Tennis Resort!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    You will pinch yourself that you are staying on such a gorgeous island in a beautiful townhome! Every morning you will l ...

    From $372 per night (USD)

    VRBO

    Details
  • Bayside condo-250 feet to beach-available summer thru January
    From $254 per night (USD)

    VRBO

    Bayside condo-250 feet to beach-available summer thru January

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Spring, summer, fall through January, here’s an opportunity to get immersed in the island lifestyle. Available starting ...

    From $254 per night (USD)

    VRBO

    Details
  • Beautiful Ground Floor Condo on Award Winning Beach
    From $253 per night (USD)

    VRBO

    Beautiful Ground Floor Condo on Award Winning Beach

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Hi everybody, if our available dates don't work, please let me know, we do have another condo and lots of friends with c ...

    From $253 per night (USD)

    VRBO

    Details
  • Beautiful Longboat Key, Perfect Location,  Sarasota ~FL~
    From $198 per night (USD)

    VRBO

    Beautiful Longboat Key, Perfect Location, Sarasota ~FL~

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    ****BACK ON THE MARKET**** Beautiful Longboat Key, Sarasota, FL! * Newly remodeled, 2 bedroom, 2 bath condo, overlook ...

    From $198 per night (USD)

    VRBO

    Details
  • Beach and Pool View 2 Bedroom Condo
    From $198 per night (USD)

    Expedia

    Beach and Pool View 2 Bedroom Condo

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Escape to Your Beachfront Oasis Awaits! Imagine waking up to the sparkling turquoise waters of the Gulf just steps away ...

    From $198 per night (USD)

    Expedia

    Details
  • Premier Beach View 2 Bedroom Condo
    From $325 per night (USD)

    VRBO

    Premier Beach View 2 Bedroom Condo

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    New Listing! Ultra-Luxury level expertly renovated 2 bedroom condo offers modern elegance. Thoughtful updating inclu ...

    From $325 per night (USD)

    VRBO

    Details
  • Full Beach View 2 Bedroom Penthouse
    From $397 per night (USD)

    Expedia

    Full Beach View 2 Bedroom Penthouse

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Penthouse level fully renovated 2 bedroom condo offers modern luxury. It is paradise within paradise. This is a very ra ...

    From $397 per night (USD)

    Expedia

    Details
  • Home away from home in LBK
    From $177 per night (USD)

    VRBO

    Home away from home in LBK

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Relax with the whole family at this peaceful place to stay. The home offers an ample attached single car garage with sto ...

    From $177 per night (USD)

    VRBO

    Details
  • Bikini Bottom Cottage in the historic village of Longboat Key
    From $172 per night (USD)

    VRBO

    Bikini Bottom Cottage in the historic village of Longboat Key

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    The Bikini bottom Cottage is on an alley way that lead directly to the kayak and boat launch. Walk down to view the sun ...

    From $172 per night (USD)

    VRBO

    Details
  • Beach View Condo-Quiet & Secluded  Private Beach
    From $439 per night (USD)

    VRBO

    Beach View Condo-Quiet & Secluded Private Beach

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Relax with your loved ones at this quiet, beachfront condo at the Beach Castle Resort with views of the Gulf of Mexico f ...

    From $439 per night (USD)

    VRBO

    Details
  • Steps from the beach on Longboat Key
    From $151 per night (USD)

    Expedia

    Steps from the beach on Longboat Key

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Charming, one-of-a-kind property in a boutique-like setting with only 11 other units. There is a beautiful, heated pool ...

    From $151 per night (USD)

    Expedia

    Details
  • Hidden Gem | Longboat Key 2BR w/ Beach Access
    From $268 per night (USD)

    VRBO

    Hidden Gem | Longboat Key 2BR w/ Beach Access

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Longboat Key offers sandy beaches and a relaxed island lifestyle. Whether you're here for a tranquil getaway or seeking ...

    From $268 per night (USD)

    VRBO

    Details
  • Waterfront Getaway Island Villa at Longboat Key
    From $186 per night (USD)

    Expedia

    Waterfront Getaway Island Villa at Longboat Key

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Relax or work remotely at our Waterfront Island Villa on LBK. Nestled 1 block from the beach & on Sarasota Bay, enjoy wa ...

    From $186 per night (USD)

    Expedia

    Details
  • Fairway Bay - Luxury Beachfront Condo with Pool by Gulfcoast Holiday Homes
    From $518 per night (USD)

    VRBO

    Fairway Bay - Luxury Beachfront Condo with Pool by Gulfcoast Holiday Homes

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    4

    Luxury Vacation Rental condo, recently remodeled, with 3 bedrooms, 2 bathrooms, and spectacular water views. Located in ...

    From $518 per night (USD)

    VRBO

    Details
  • Beachplace 8-505 Gulf Front by FVC
    From $286 per night (USD)

    Expedia

    Beachplace 8-505 Gulf Front by FVC

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Beachfront Bliss at Beachplace – Your Longboat Key Retreat Welcome to your dream coastal getaway, professionally manag ...

    From $286 per night (USD)

    Expedia

    Details
  • Stunning 2 BR Condo views of the Gulf and Lake
    From $253 per night (USD)

    VRBO

    Stunning 2 BR Condo views of the Gulf and Lake

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Spacious 2 bedroom condo in Beachplace gated complex. King in Master bedroom. Come enjoy your time at the Beach. This ...

    From $253 per night (USD)

    VRBO

    Details
  • Penthouse level with Beach View 2 Bedroom Condo
    From $280 per night (USD)

    Expedia

    Penthouse level with Beach View 2 Bedroom Condo

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Penthouse unit on the top floor of building 3 at Beachplace. Top floor units enjoy a double balcony with access from t ...

    From $280 per night (USD)

    Expedia

    Details
  • Partial Beach View 3 Bedroom Condo
    From $282 per night (USD)

    VRBO

    Partial Beach View 3 Bedroom Condo

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Beautiful partial beachview unit on the 2nd floor with lake view and Beach View. Hard to find beautifully appointed 3 be ...

    From $282 per night (USD)

    VRBO

    Details
  • The Promenade
    From $582 per night (USD)

    Expedia

    The Promenade

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    2400Sq/Ft area, charming with 3 lovelly beds and 3 full baths..Condo full of ameneties, concierge, heated pool, privite ...

    From $582 per night (USD)

    Expedia

    Details
  • Longboat Key beach house - 5 min walk to the beaches and top local restaurants
    From $375 per night (USD)

    VRBO

    Longboat Key beach house - 5 min walk to the beaches and top local restaurants

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Quiet beach house tucked away in the historic Longboat Village in walking distance to the beach and some of the top rest ...

    From $375 per night (USD)

    VRBO

    Details
  • Completely Refurbished - Gorgeous Beachside Condo/Townhome on Longboat Key Beach
    From $287 per night (USD)

    Expedia

    Completely Refurbished - Gorgeous Beachside Condo/Townhome on Longboat Key Beach

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

    Experience the intimacy and warmth of northern Longboat Key at Club Longboat Beach and Tennis Resort. This 3-bedroom/ 2. ...

    From $287 per night (USD)

    Expedia

    Details
  • Beachfront!  Gorgeous gulf views, stunning sunsets, high end condo!
    From $514 per night (USD)

    VRBO

    Beachfront! Gorgeous gulf views, stunning sunsets, high end condo!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Come spend your winter at our wonderful piece of paradise! Direct beachfront, gorgeous sunsets from the large balcony ...

    From $514 per night (USD)

    VRBO

    Details
  • Beach Bliss Across the Street: Your 2BR Condo Awaits
    From $260 per night (USD)

    Expedia

    Beach Bliss Across the Street: Your 2BR Condo Awaits

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Step into a world where beachy charm and modern convenience come together! This delightful two-bedroom bayside condo, ju ...

    From $260 per night (USD)

    Expedia

    Details
  • Flip-Flops Required: Your Beachside Bliss Awaits on Longboat Key!
    From $221 per night (USD)

    VRBO

    Flip-Flops Required: Your Beachside Bliss Awaits on Longboat Key!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Ready for sun-soaked days and barefoot evenings? Gulf Tides is your summer escape—where the days are long, the pace is s ...

    From $221 per night (USD)

    VRBO

    Details
  • Beautiful Longboat Key Condo Surrounded by Ocean
    From $235 per night (USD)

    VRBO

    Beautiful Longboat Key Condo Surrounded by Ocean

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Immerse yourself in this beautiful 2 bedroom, 2 bathroom condo just steps away from one of the most beautiful beaches in ...

    From $235 per night (USD)

    VRBO

    Details
  • Cozy private beach condo
    From $226 per night (USD)

    VRBO

    Cozy private beach condo

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Relax with the whole family at this peaceful place to stay steps away from the legendary longboat key private beach! Enj ...

    From $226 per night (USD)

    VRBO

    Details
  • Steps from the Water with Spectacular Bay Views
    From $182 per night (USD)

    VRBO

    Steps from the Water with Spectacular Bay Views

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Wake up every morning and have coffee from your front patio, just a few feet away from the water. Play a round of pickle ...

    From $182 per night (USD)

    VRBO

    Details
  • Waterfront condo with Gulf views, pool, tennis, & deeded beach access
    From $163 per night (USD)

    VRBO

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

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Whitney Beach 149 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...

    From $163 per night (USD)

    VRBO

    Details
  • Ground level, Bayview condo with Private beach parking
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    Expedia

    Ground level, Bayview condo with Private beach parking

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Have your morning coffee with the dolphins and manatees in this one bedroom, one bath ,bay view unique unit. Enjoy Priva ...

    Click For Pricing

    Expedia

    Details
  • Island Living on Longboat Key 3 minute walk to the beach!
    From $311 per night (USD)

    VRBO

    Island Living on Longboat Key 3 minute walk to the beach!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Longboat Key Island Fun in a newly updated beautiful property! Newly updated 3 story townhouse on beautiful Longboat Key ...

    From $311 per night (USD)

    VRBO

    Details
  • Beachplace Penthouse Gulf Front Paradise
    From $496 per night (USD)

    Expedia

    Beachplace Penthouse Gulf Front Paradise

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    PENTHOUSE, DOUBLE BALCONIES, breathtaking wide sweeping straight on views of the Gulf and Bay make our Beachplace condo ...

    From $496 per night (USD)

    Expedia

    Details
  • Short walk to beach or take your boat from the canal  / dock in your backyard!
    From $208 per night (USD)

    VRBO

    Short walk to beach or take your boat from the canal / dock in your backyard!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    This house offers the best of island living - a boat dock out back and deeded private access to the white sandy beaches ...

    From $208 per night (USD)

    VRBO

    Details
  • No hurricane damage inside! Gulf front, first floor, two bedroom. A hidden gem!
    From $441 per night (USD)

    Expedia

    No hurricane damage inside! Gulf front, first floor, two bedroom. A hidden gem!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Paradise found! Gorgeous. Two bedroom, two full bathrooms. Open concept. Leather couches, luxurious bathrooms. Master ...

    From $441 per night (USD)

    Expedia

    Details
  • Cute canal front Cottage with dock & boat lift and pool ,short walk to the beach
    From $416 per night (USD)

    VRBO

    Cute canal front Cottage with dock & boat lift and pool ,short walk to the beach

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    What's better than your own private paradise? Come and enjoy this beautiful, recently remodeled, canal front 2 bedroom ...

    From $416 per night (USD)

    VRBO

    Details
  • Contemporary Coastal Retreat w Gourmet Kitchen & Stunning Gulf Views by RVA
    From $1014 per night (USD)

    Expedia

    Contemporary Coastal Retreat w Gourmet Kitchen & Stunning Gulf Views by RVA

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    This exquisite Sea Grape Inn is just steps from the sandy beaches of Longboat Key and features a private infinity pool w ...

    From $1014 per night (USD)

    Expedia

    Details
  • Island property on Longboat Key by the Beach! 3 minute walk to the beach!
    From $311 per night (USD)

    VRBO

    Island property on Longboat Key by the Beach! 3 minute walk to the beach!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Longboat Key Island Fun in a newly updated beautiful property! Newly updated 3 story townhouse on beautiful Longboat Key ...

    From $311 per night (USD)

    VRBO

    Details
  • Starfish Paradise-Beachfront Oasis w Screened Patio & Stunning Sunsets by RVA
    From $379 per night (USD)

    Expedia

    Starfish Paradise-Beachfront Oasis w Screened Patio & Stunning Sunsets by RVA

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Welcoming Starfish Paradise to RVA's collection of vacation rentals, where a well-deserved beach vacation is guaranteed. ...

    From $379 per night (USD)

    Expedia

    Details
  • Longboat Key Vacation Rental: Direct Beach Access!
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    VRBO

    Longboat Key Vacation Rental: Direct Beach Access!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Experience the coastal charm of Longboat Key when you book this fantastic 1-bedroom, 1-bathroom condo! Perfect for coupl ...

    Click For Pricing

    VRBO

    Details
  • SUNSET VISTA ON LONGBOAT KEY
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    Expedia

    SUNSET VISTA ON LONGBOAT KEY

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Gorgeous 1,110 sq.ft., renovated condo on the 3rd floor in Beach Harbor Club. This 2 bedroom/ 2 bath condo has been comp ...

    Click For Pricing

    Expedia

    Details
  • Bay-view condo with boat access, 2 outdoor pools, balcony, BBQ area, W/Ds
    From $308 per night (USD)

    VRBO

    Bay-view condo with boat access, 2 outdoor pools, balcony, BBQ area, W/Ds

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Another Day In Paradise Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...

    From $308 per night (USD)

    VRBO

    Details
  • Whitney Beach 321 2brm beachfront
    From $447 per night (USD)

    Expedia

    Whitney Beach 321 2brm beachfront

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Summary: Immerse yourself in refined luxury with this impeccably designed Whitney Beach #321. This condo offers spacious ...

    From $447 per night (USD)

    Expedia

    Details
  • Whitney Beach 319 2brm beachfront
    From $264 per night (USD)

    VRBO

    Whitney Beach 319 2brm beachfront

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Summary: Experience this ground floor 2 brm/2 bath Unit# 319 at the Whitney Beach III condo complex on Longboat Key. Ent ...

    From $264 per night (USD)

    VRBO

    Details
  • Whitney Beach 320 1brm beachfront condo
    From $302 per night (USD)

    Expedia

    Whitney Beach 320 1brm beachfront condo

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Summary: A completely renovated ground-floor 1 brm/1bath beachfront condo awaits you in Longboat Key's lifestyle of luxu ...

    From $302 per night (USD)

    Expedia

    Details
  • Beach Castle Resort, 1st Floor, Pool, Walk to Beach/Bay
    From $357 per night (USD)

    VRBO

    Beach Castle Resort, 1st Floor, Pool, Walk to Beach/Bay

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Escape to a tranquil paradise on Longboat Key and discover the hidden gem known as Pura Vida, a delightful 2-bedroom, 2- ...

    From $357 per night (USD)

    VRBO

    Details
  • Tropical Escape–Private Pool Home Near the Sand Hy Tee on Longboat Key by RVA
    From $303 per night (USD)

    Expedia

    Tropical Escape–Private Pool Home Near the Sand Hy Tee on Longboat Key by RVA

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to Hy Tee, a charming coastal retreat nestled on Longboat Key, Florida. This beautiful vacation home promises a ...

    From $303 per night (USD)

    Expedia

    Details
  • 2BR Cottage Bay Views Bayside
    From $324 per night (USD)

    VRBO

    2BR Cottage Bay Views Bayside

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    This spacious retreat features a king bed in the main bedroom, ideal for recharging after a day of beach adventures. The ...

    From $324 per night (USD)

    VRBO

    Details
  • Sutton Place with Private Beach, Pavilion with Grills/Showers, 2 Pools
    From $224 per night (USD)

    Expedia

    Sutton Place with Private Beach, Pavilion with Grills/Showers, 2 Pools

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Escape to paradise with this beautifully furnished 2-bedroom, 2-bathroom townhome on Longboat Key, Florida. With a beach ...

    From $224 per night (USD)

    Expedia

    Details
  • 3BR Cottage- Footsteps to the Sand
    From $634 per night (USD)

    VRBO

    3BR Cottage- Footsteps to the Sand

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Step into the charm of Old Florida with this 3-bedroom, 2-bath coastal cottage just steps from the warm waters of the Gu ...

    From $634 per night (USD)

    VRBO

    Details
  • 1BR Gulf Breezes & Old Florida Charm
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    Expedia

    1BR Gulf Breezes & Old Florida Charm

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Kick off your shoes and settle into the easy rhythm of coastal living. Start your mornings with a stroll along the soft ...

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  • 1BR Gulfside Cottage Watch the Sunset from the Sandy Shores
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    1BR Gulfside Cottage Watch the Sunset from the Sandy Shores

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Step onto the porch, take a deep breath, and let the salty sea air remind you—you’re officially on beach time. Whether i ...

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  • Exquisite Views Gulf-Front 2 BR Condo
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    Exquisite Views Gulf-Front 2 BR Condo

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    This two-bedroom, two-bath gulf front retreat is designed for a relaxing and unforgettable stay, complete with all the c ...

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  • Bayside 2BR Villa on Longboat Key
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    Bayside 2BR Villa on Longboat Key

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    This two-bedroom, two-bath, bayside villa offers all the essentials needed for a vacation at the beach. The kitchen is w ...

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  • BOOK NOW - BEAUTIFUL HOME, BEACH ACCESS!!
    From $477 per night (USD)

    Expedia

    BOOK NOW - BEAUTIFUL HOME, BEACH ACCESS!!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    12

    ISLAND PARADISE!!! Enjoy this spectacular home in a beautiful, very quiet, Longboat Key neighbourhood. Take a leisurely ...

    From $477 per night (USD)

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  • Perfect cottage! Million dollar views
    From $194 per night (USD)

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    Perfect cottage! Million dollar views

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Adorable beach cottage with million dollar views of Sarasota Bay out front and a canal out back. Gorgeous seating in bot ...

    From $194 per night (USD)

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  • 1st Floor Beachfront Luxury–Ocean Views Included Club Longboat #516 by RVA
    From $287 per night (USD)

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    1st Floor Beachfront Luxury–Ocean Views Included Club Longboat #516 by RVA

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    RVA invites you to experience the intimacy and warmth of northern Longboat Key at Club Longboat Beach and Tennis Resort. ...

    From $287 per night (USD)

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  • Relax in a Spacious Townhouse on Beautiful Longboat Key!
    From $209 per night (USD)

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    Relax in a Spacious Townhouse on Beautiful Longboat Key!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Enjoy paradise in a spacious 2 bedroom & 2-1/2 bathroom townhome. The property backs up to conservation land which can ...

    From $209 per night (USD)

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  • Cozy condo in Cedars East
    From $221 per night (USD)

    VRBO

    Cozy condo in Cedars East

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Cozy Condo in Cedars East is a place for you to unwind and revive yourself. Only a 5 minute walk to the beach. Close to ...

    From $221 per night (USD)

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  • Beachcomber unit 504
    From $432 per night (USD)

    VRBO

    Beachcomber unit 504

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    The Beachcomber is a jewel on the luxurious island of Longboat Key, located directly on the white sandy beach of the Gul ...

    From $432 per night (USD)

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  • Dolphin’s Den: Seaside Escape w Rooftop Gulf Views & Private Beach by RVA
    From $327 per night (USD)

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    Dolphin’s Den: Seaside Escape w Rooftop Gulf Views & Private Beach by RVA

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Experience this peaceful beach vibe at the Dolphin's Den in Longboat Key located in a clean, quiet private cul-de-sac. J ...

    From $327 per night (USD)

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  • The HEART of Longboat Key
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    The HEART of Longboat Key

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    1

    Welcome to your home away from home! Sit back and relax beachside in the premier location of Longboat Key. The promenade ...

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  • Canal Front Home - 8 min walk to beach.  RRR-00953.2023
    From $448 per night (USD)

    Expedia

    Canal Front Home - 8 min walk to beach. RRR-00953.2023

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Completely remodeled in 2022 this canal front with pool home is located on the beautiful Island of Longboat Key. Pull y ...

    From $448 per night (USD)

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  • Longboat Key Cedars Beach House-Pet Friendly-2 Minute Walk To The Beach
    From $222 per night (USD)

    VRBO

    Longboat Key Cedars Beach House-Pet Friendly-2 Minute Walk To The Beach

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    We understand that plans can change, and we want you to book your stay with peace of mind. That’s why we offer the most ...

    From $222 per night (USD)

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  • Unit #318 Sand Cay Beach Resort Gulf Front
    From $543 per night (USD)

    Expedia

    Unit #318 Sand Cay Beach Resort Gulf Front

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Unwind and make memories in this sun-filled unit with stunning Gulf-front and beach views. Accommodation for up to 6 wit ...

    From $543 per night (USD)

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  • Bay Haven Home on Longboat Key by RVA
    From $327 per night (USD)

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    Bay Haven Home on Longboat Key by RVA

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to Bay Haven Home by RVA in the popular community of Country Club Shores. A large master bedroom suite, two gues ...

    From $327 per night (USD)

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  • Beach front
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    Beach front

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    2

    just walk to the beach out of the building. Watch sunrises and sunsets at the balcony. Common area: gym at the clubhous ...

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  • Cedars East Tennis Escape–Pet-Friendly & Near the Beach Unit #847 by RVA
    From $268 per night (USD)

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    Cedars East Tennis Escape–Pet-Friendly & Near the Beach Unit #847 by RVA

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    RVA features Cedars Tennis Resort, a luxury vacation rental on Longboat Key where world-class facilities, magnificent be ...

    From $268 per night (USD)

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  • Whitney Beach Tropical Getaway–Bayside 2 BR Condo w Private Shoreline by RVA
    From $346 per night (USD)

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    Whitney Beach Tropical Getaway–Bayside 2 BR Condo w Private Shoreline by RVA

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Experience the intimacy and warmth of northern Longboat Key at Whitney Beach. Located on a superb pristine beach with ne ...

    From $346 per night (USD)

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  • Charming Gulfside Getaway: Sea Twig 101-2BR Condo w Easy Beach Access by RVA
    From $239 per night (USD)

    VRBO

    Charming Gulfside Getaway: Sea Twig 101-2BR Condo w Easy Beach Access by RVA

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    RVA features an intimate beachfront condominium property on the Gulf of Mexico. The quiet beach can be reached by charmi ...

    From $239 per night (USD)

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  • Tennis resort Townhome on longboat key by the Sea. Family and pet friendly
    From $158 per night (USD)

    Expedia

    Tennis resort Townhome on longboat key by the Sea. Family and pet friendly

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    This vacation home is a 2-bedroom, 2-bathroom town home with garden views from your private lanai and clubhouse views fr ...

    From $158 per night (USD)

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    Details
  • Beach, Boat & Pool–Coastal Home Has It All! Lyons Lane-Longboat Key by RVA
    From $431 per night (USD)

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    Beach, Boat & Pool–Coastal Home Has It All! Lyons Lane-Longboat Key by RVA

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    RVA presents this spacious vacation home that represents what Island Living is all about! Lyons Lane sits on a quiet st ...

    From $431 per night (USD)

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  • 3 brm pool home on Longboat Key by FVC
    From $290 per night (USD)

    Expedia

    3 brm pool home on Longboat Key by FVC

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Enchantment – Proudly Offered and Professionally Managed by FL Vacation Connection Nestled along a serene canal, this s ...

    From $290 per night (USD)

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  • Beautifully remodeled condo with lots of amenities!
    From $236 per night (USD)

    VRBO

    Beautifully remodeled condo with lots of amenities!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Seasonal Turnkey Furnished Rental at Bayport Beach and Tennis Club. Available now and for 20231 You will fall in love wi ...

    From $236 per night (USD)

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  • Beach Cottage with a Private Hot Tub
    From $143 per night (USD)

    Expedia

    Beach Cottage with a Private Hot Tub

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Welcome to this beach cottage on Longboat Key directly across the street from beautiful white sand beach with private be ...

    From $143 per night (USD)

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  • Steps to the Sand: Gulfside 2BR at Whitney Beach w Pool & Sunset Views by RVA
    From $578 per night (USD)

    VRBO

    Steps to the Sand: Gulfside 2BR at Whitney Beach w Pool & Sunset Views by RVA

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Experience the intimacy and warmth of northern Longboat Key at Whitney Beach. Located on the pristine Longboat Key beach ...

    From $578 per night (USD)

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  • Delightful 2/2 Beach House LBK 5 Min walk to Beach
    From $145 per night (USD)

    Expedia

    Delightful 2/2 Beach House LBK 5 Min walk to Beach

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    OUTSTANDING LOCATION on LONGBOAT KEY, only a 5-minute walk to the gorgeous beach! This delightful beach house is 1,404 ...

    From $145 per night (USD)

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  • Waterfront ❤ Spa/Pool ❤ Private Paradise on LBK !
    From $318 per night (USD)

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    Waterfront ❤ Spa/Pool ❤ Private Paradise on LBK !

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Looking for the ULTIMATE Beach getaway? This is it! Welcome to paradise at the Harbour Villa Club. 2 Bedrooms, 2 Baths w ...

    From $318 per night (USD)

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  • Luxury Condo  located on Beachfront  Property
    From $364 per night (USD)

    VRBO

    Luxury Condo located on Beachfront Property

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    . The condo is situated in one of the most beautiful Beachfront Properties in Longboat Key. The lush landscape along w ...

    From $364 per night (USD)

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  • Amazing Beachfront 2B/2B in Longboat Key
    From $118 per night (USD)

    VRBO

    Amazing Beachfront 2B/2B in Longboat Key

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    October and November 2021 are still available with Deep Discount Prices! Wonderful Beachfront condo in magnificent Lo ...

    From $118 per night (USD)

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  • Welcome to your Beach Front Dream Condo! LBKTP102
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    Welcome to your Beach Front Dream Condo! LBKTP102

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Gulf Front Longboat Key Vacation Rental! 2 bedrooms, 2 baths, over 1300 square feet under air, walk right out to the bea ...

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  • Silver Sands, Oceanfront - Gulf Beach Resort
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    Silver Sands, Oceanfront - Gulf Beach Resort

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    55 steps away from the Gulf of Mexico Beach! Beautiful beach with the most amazing sunsets. Family friendly resort wit ...

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  • Luxury 4 brm home by FVC
    From $866 per night (USD)

    Expedia

    Luxury 4 brm home by FVC

    Bedrooms:
    5
    Bathrooms:
    4
    Sleeps:
    10

    Welcome to one of the most picturesque views on Longboat Key. Elegance, privacy and nature abound in this stunning Long ...

    From $866 per night (USD)

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  • Peaceful Longboat Key Canal Home
    From $315 per night (USD)

    VRBO

    Peaceful Longboat Key Canal Home

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Enjoy the complete island experience in this 2-story two bedroom, one and a half bath, canal front condo, with boat dock ...

    From $315 per night (USD)

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  • Newly Renovated Tree House Condo Across The Street to the Beach!
    From $420 per night (USD)

    VRBO

    Newly Renovated Tree House Condo Across The Street to the Beach!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Enjoy the outdoor heated pool or take a 1 min stroll across the street to the Gulf of Mexico where our pristine beaches ...

    From $420 per night (USD)

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  • Gulf Beach Resort - B
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    Gulf Beach Resort - B

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Unit Features: 1-bedroom, 1-bathroom unit in the Orange Building Layout Note: Please note, the front door to unit 245 op ...

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  • Gulf Beach Resort - A
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    Gulf Beach Resort - A

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    RVA offers Silver Sands Gulf Beach Resort. Located beach front on beautiful Longboat Key, this resort offers all the ame ...

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  • BEAUTIFUL GULF-VIEW CONDO
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    BEAUTIFUL GULF-VIEW CONDO

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    2

    Spectacular balcony and window views sitting on the Gulf. Private beach, swimming pool and tennis court. Spacious unit ...

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  • Gulf Front 3 bedroom Condo in Club Longboat
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    Gulf Front 3 bedroom Condo in Club Longboat

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    This beautiful, ground floor, gulf front, condo in Club Longboat features two full bedrooms, two full baths, a den with ...

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