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Results: 925 Rentals

  • New Listing: Sun, Sea Breeze & Seagulls – The Ultimate Beach Location
    From $269 per night (USD)

    VRBO

    New Listing: Sun, Sea Breeze & Seagulls – The Ultimate Beach Location

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Located in the heart of Longboat Key Gulf Key provides it’ guest with one of the best locations on the key. With two (2) ...

    From $269 per night (USD)

    VRBO

    Details
  • Coquina Moorings 201 - Anna Maria Island - Condo 2 Bedroom\/ 2 Bath with...
    From $411 per night (USD)

    Expedia

    Coquina Moorings 201 - Anna Maria Island - Condo 2 Bedroom\/ 2 Bath with...

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Coquina Moorings, Unit 201 - Anna Maria Island - 2 Bedroom/ 2 Bath with Den, maximum occupancy of 6 people. Bay an ...

    From $411 per night (USD)

    Expedia

    Details
  • Recently Updated!!!  Lovely 2 Bedroom Condo in Bayport Beach and Tennis Club
    From $204 per night (USD)

    VRBO

    Recently Updated!!! Lovely 2 Bedroom Condo in Bayport Beach and Tennis Club

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    This tastefully furnished, second-floor condo in the Bayport Beach and Tennis Club offers a comfortable living space wit ...

    From $204 per night (USD)

    VRBO

    Details
  • Beautiful beachfront condo on Longboat Key, FL!!!
    From $468 per night (USD)

    Expedia

    Beautiful beachfront condo on Longboat Key, FL!!!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Direct Beachfront, Longboat Key remodeled 2/2 Condo in Beachplace. Beautiful Beachplace is a gated community located on ...

    From $468 per night (USD)

    Expedia

    Details
  • The Linley Bungalow - Pool home in the Village of Longboat Key.  Walk to restaurants and beach!
    From $202 per night (USD)

    VRBO

    The Linley Bungalow - Pool home in the Village of Longboat Key. Walk to restaurants and beach!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Linley Bungalow.....Cute 1 bedroom, 1.5 bath, beach bungalow is the perfect compact pool home for those looking for a la ...

    From $202 per night (USD)

    VRBO

    Details
  • 637 Norton - Longboat Key - Private canal home 4 Bedroom\/ 3.5 Bath with...
    From $789 per night (USD)

    Expedia

    637 Norton - Longboat Key - Private canal home 4 Bedroom\/ 3.5 Bath with...

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    637 Norton - Longboat Key - 4 Bedroom/ 3.5 Bath, maximum occupancy of 8 people. Canal Home - Private Pool - Boat D ...

    From $789 per night (USD)

    Expedia

    Details
  • The Beach on Longboat Key #221 Resort by RVA
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    VRBO

    The Beach on Longboat Key #221 Resort by RVA

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    RVA features The Beach on Longboat Key. Savor warm Gulf breezes while resting lavishly in this Gulf-front condominium co ...

    Click For Pricing

    VRBO

    Details
  • Beautiful, Recently Renovated 2br \/ 2b Gulf Front Condo.
    From $339 per night (USD)

    Expedia

    Beautiful, Recently Renovated 2br \/ 2b Gulf Front Condo.

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    6

    This beautiful condo is furnished in island style furniture. It includes an inside entry, washer/dryer, big screen TV, f ...

    From $339 per night (USD)

    Expedia

    Details
  • Walk to Everything, Gulf Views, Waterfront, Heated Resort Style Pool w\/ Slide
    From $1834 per night (USD)

    VRBO

    Walk to Everything, Gulf Views, Waterfront, Heated Resort Style Pool w\/ Slide

    Bedrooms:
    7
    Bathrooms:
    6
    Sleeps:
    16

    Vunique Vacations - Distinct vacation homes for the discerning traveler who is seeking a truly unforgettable vacation ex ...

    From $1834 per night (USD)

    VRBO

    Details
  • Longboat Key Resort Escape - Walk to the Beach!
    From $311 per night (USD)

    Expedia

    Longboat Key Resort Escape - Walk to the Beach!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Prepare yourself for a Gulf Coast getaway at this welcoming 1-bed, 1-bath vacation rental nestled in the tropical Beach ...

    From $311 per night (USD)

    Expedia

    Details
  • Blue Heron House on Longboat Key by RVA
    From $287 per night (USD)

    VRBO

    Blue Heron House on Longboat Key by RVA

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to Blue Heron House by RVA. This three-bedroom plus office, two-bathroom house is located on the Northern end of ...

    From $287 per night (USD)

    VRBO

    Details
  • Ocean view Longboat Key condo
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    Expedia

    Ocean view Longboat Key condo

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    2 BR/2 BA spacious condo timeshare at the Veranda Beach Club in Longboat Key with Gulf of Mexico views from the balcony. ...

    Click For Pricing

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  • Discounted rates for May! Direct bayfront views!
    From $232 per night (USD)

    VRBO

    Discounted rates for May! Direct bayfront views!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

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

    From $232 per night (USD)

    VRBO

    Details
  • LONGBOAT KEY BEAUTY! This 2\/2 unit offers stunning views of the bay! Call today to book your fall vacation!
    From $227 per night (USD)

    Expedia

    LONGBOAT KEY BEAUTY! This 2\/2 unit offers stunning views of the bay! Call today to book your fall vacation!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    • Carefree check-in, go straight to your unit no office visit required. • Fully Equipped Kitchen including microwave, st ...

    From $227 per night (USD)

    Expedia

    Details
  • The Beach on Longboat Key #221S Resort by RVA
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    VRBO

    The Beach on Longboat Key #221S Resort by RVA

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    RVA features The Beach on Longboat Key. Savor warm Gulf breezes while resting lavishly in this Gulf-front condominium co ...

    Click For Pricing

    VRBO

    Details
  • The Beach on Longboat Key #220 Resort by RVA
    Click For Pricing

    Expedia

    The Beach on Longboat Key #220 Resort by RVA

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    RVA features The Beach on Longboat Key. Savor warm Gulf breezes while resting lavishly in this Gulf-front condominium co ...

    Click For Pricing

    Expedia

    Details
  • Little Gull Resort - Longboat Key, Florida
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    VRBO

    Little Gull Resort - Longboat Key, Florida

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    Large 4 bedroom Suite on beautiful Sarasota Bay. 2 bathroom Pull-out sofa bed sleeps 2. Large verandah with a great vie ...

    Click For Pricing

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    Details
  • Right on the beach.Renovated ground Floor unit 63.
    From $331 per night (USD)

    Expedia

    Right on the beach.Renovated ground Floor unit 63.

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Completely renovated. Everything is new. Amazing location. Charming studio right on the beach. Condo management will he ...

    From $331 per night (USD)

    Expedia

    Details
  • Bright Key West style home on the Longboat Key-Walk to the Beach
    From $500 per night (USD)

    VRBO

    Bright Key West style home on the Longboat Key-Walk to the Beach

    Bedrooms:
    4
    Bathrooms:
    3
    Sleeps:
    6

    Enjoy a great vacation home on the north end of Longboat Key near Longboat Pass. This home is set on a lovely bayou and ...

    From $500 per night (USD)

    VRBO

    Details
  • beachfront condo on 6th floor of the   longboat key club resort !
    Click For Pricing

    Expedia

    beachfront condo on 6th floor of the longboat key club resort !

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    6th floor bedroom king suite with 1 bathroom living room area with pull out queen bed and kitchen with washer dryer con ...

    Click For Pricing

    Expedia

    Details
  • Upscale Beachplace Condo...summer 2025 now discounted 15%...please inquire
    From $197 per night (USD)

    VRBO

    Upscale Beachplace Condo...summer 2025 now discounted 15%...please inquire

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    LATEST NEWSFLASH FOR BEACHPLACE UNIT 4-404: * The following months in 2025 are available....May, August, September, Oct ...

    From $197 per night (USD)

    VRBO

    Details
  • LONGBOAT KEY BEACH CONDO
    From $454 per night (USD)

    Expedia

    LONGBOAT KEY BEACH CONDO

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to our Longboat Key (LBK) Family Home. Our condo is a true family home where we gather together to get away fr ...

    From $454 per night (USD)

    Expedia

    Details
  • Longboat Key Cottage: Extended Stays Welcome!
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    VRBO

    Longboat Key Cottage: Extended Stays Welcome!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Head to Florida for a much-needed, month-long getaway when you book and stay at this amenity-packed 2-bedroom, 2-bathroo ...

    Click For Pricing

    VRBO

    Details
  • Beachplace - 6  305, 3 Bedroom Condo with Gulf and Bay views
    From $241 per night (USD)

    Expedia

    Beachplace - 6 305, 3 Bedroom Condo with Gulf and Bay views

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    All the bells and whistles! This is a gorgeous 3 bedroom/2 bath corner unit with wrap around windows! Beautiful open con ...

    From $241 per night (USD)

    Expedia

    Details
  • 2 Bd\/2 Bath Condo on Sarasota Bay Across from Gulf of Mexico 3-6 month rental
    From $171 per night (USD)

    VRBO

    2 Bd\/2 Bath Condo on Sarasota Bay Across from Gulf of Mexico 3-6 month rental

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Available from June 1st - December 15, 2023. Long-term renter desired. Beautiful corner unit condo with an abundance of ...

    From $171 per night (USD)

    VRBO

    Details
  • Beautiful Longboat Key, Florida - Little Gull Resort
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    Expedia

    Beautiful Longboat Key, Florida - Little Gull Resort

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    6

    Large 2 bedroom, 2 bathroom suite (plus pull-out sofa bed) Fully equipped kitchen with dishwasher 3 TVs and WIFI Firepla ...

    Click For Pricing

    Expedia

    Details
  • Gulf Front 3 bedroom Condo in Club Longboat
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    VRBO

    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 ...

    Click For Pricing

    VRBO

    Details
  • Perfect FL Longboat Key Getaway, steps from the Gulf! Sleeps 4
    From $253 per night (USD)

    Expedia

    Perfect FL Longboat Key Getaway, steps from the Gulf! Sleeps 4

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    This 1st floor, 1 bedroom/1 bathroom beautifully and newly decorated condo is located directly across the street (beach ...

    From $253 per night (USD)

    Expedia

    Details
  • Updated Townhome, Secluded Beach + Pool
    From $381 per night (USD)

    VRBO

    Updated Townhome, Secluded Beach + Pool

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Renovation completed in 2025! New master bath, whole house repaint, new furniture, etc. Longboat Key beach is ok post-hu ...

    From $381 per night (USD)

    VRBO

    Details
  • 2Bd+2 Ba beach cottage w\/private front\/back yard, screened porch, firepit, grill
    From $440 per night (USD)

    Expedia

    2Bd+2 Ba beach cottage w\/private front\/back yard, screened porch, firepit, grill

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Perfect, private retreat! Time slips into Beach time, where nature guides your days and evenings. Fully renovated post 2 ...

    From $440 per night (USD)

    Expedia

    Details
  • We Are Open!  No damage to our Beautiful Beachfront Condo on Gulf of Mexico
    From $403 per night (USD)

    VRBO

    We Are Open! No damage to our Beautiful Beachfront Condo on Gulf of Mexico

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Hi everybody, we are happy to report that our unit incurred no damage and our association had only minimal damage due to ...

    From $403 per night (USD)

    VRBO

    Details
  • Lido Key Getaway With Heated Private Pool and Private Beach Access
    From $392 per night (USD)

    Expedia

    Lido Key Getaway With Heated Private Pool and Private Beach Access

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    This amazing mid-century modern home is the perfect Lido Key getaway for relaxation and vacation in Florida. Steps from ...

    From $392 per night (USD)

    Expedia

    Details
  • Sea Grape Inn#8- Beach Front Condo
    From $933 per night (USD)

    VRBO

    Sea Grape Inn#8- Beach Front Condo

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    BEACH FRONT Condo- 2nd Floor of Beach Front Property, 3 Bdrms/2.5 Baths or UPGRADE to 4 Bdrms/ 3.5 Baths Condo! 3 BDRMS ...

    From $933 per night (USD)

    VRBO

    Details
  • Longbeach Lucky #13 Condo by RVA
    From $214 per night (USD)

    Expedia

    Longbeach Lucky #13 Condo by RVA

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    No luck needed here to know you've stumbled upon one of the best spots Longboat Key has to offer. Longbeach Lucky 13 by ...

    From $214 per night (USD)

    Expedia

    Details
  • Stunning Modern Villa with Private Pool&Dock on Longboat Key.Your Dream Getaway!
    From $498 per night (USD)

    VRBO

    Stunning Modern Villa with Private Pool&Dock on Longboat Key.Your Dream Getaway!

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    6

    Experience the Ultimate Getaway at Our Brand New Villa on Longboat Key! NO HURRICANE DAMAGE!!! Escape to paradise in o ...

    From $498 per night (USD)

    VRBO

    Details
  • Spectacular Views of Beach and Bay
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    Expedia

    Spectacular Views of Beach and Bay

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    3 month minimum rental no smoking no pets. We are renting our turnkey condo fully furnished including all utilities. The ...

    Click For Pricing

    Expedia

    Details
  • Exquisite Beachfront Condo with both Sunrise & Sunset Views
    From $370 per night (USD)

    VRBO

    Exquisite Beachfront Condo with both Sunrise & Sunset Views

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    A tropical treasure is waiting for you. Newly renovated beachfront beauty with Tommy Bahama inspired furnishings through ...

    From $370 per night (USD)

    VRBO

    Details
  • Coquina Moorings 103 ~ Beach, Bay, Pool, Docking
    From $418 per night (USD)

    Expedia

    Coquina Moorings 103 ~ Beach, Bay, Pool, Docking

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Coquina Moorings offers the BEST of both worlds... The Beach and The Bay! Spectacular views from the main living area, ...

    From $418 per night (USD)

    Expedia

    Details
  • Big Roomy Beach Cottage: 4 bd\/3 ba -2,000 sq ft; 100 ft to beach path; priv pool
    From $678 per night (USD)

    VRBO

    Big Roomy Beach Cottage: 4 bd\/3 ba -2,000 sq ft; 100 ft to beach path; priv pool

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    10

    One level FL Beach Cottage, 3rd house from Beach Path on N end of Lido Beach. This is a rare find in a nice quiet neighb ...

    From $678 per night (USD)

    VRBO

    Details
  • Direct gulf view!!!!
    From $299 per night (USD)

    Expedia

    Direct gulf view!!!!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    2 bedroom, 2 bath condo located directly on the Gulf of Mexico on beautiful Longboat Key, Florida!! Both condos sleep ...

    From $299 per night (USD)

    Expedia

    Details
  • SPECTACULAR GULF OF MEXICO VIEWS ON LONGBOAT KEY!!
    From $258 per night (USD)

    VRBO

    SPECTACULAR GULF OF MEXICO VIEWS ON LONGBOAT KEY!!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    3 bedroom, 2 full bath 3rd Floor (Top Floor)-Southwest Corner 1500+ sq./ft. of living space Bedrooms (Sleeps 6): Bedroo ...

    From $258 per night (USD)

    VRBO

    Details
  • Stunning Views, Directly on beach, Pool, Private Corner Unit
    From $418 per night (USD)

    Expedia

    Stunning Views, Directly on beach, Pool, Private Corner Unit

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Please Inquire with any questions or possible adjustments to dates. You will love the mesmerizing views of the Gulf of M ...

    From $418 per night (USD)

    Expedia

    Details
  • Waterfront Condo in Longboat Key Florida
    From $192 per night (USD)

    VRBO

    Waterfront Condo in Longboat Key Florida

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Waterfront 1 bedroom, 1 bath ground floor walk out condominium. Water views from ALL rooms. The lanai/sun room is set up ...

    From $192 per night (USD)

    VRBO

    Details
  • Sunlit Longboat Key Escape w\/ Private Resort Beach
    From $308 per night (USD)

    Expedia

    Sunlit Longboat Key Escape w\/ Private Resort Beach

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Whether you're looking to escape the mid-winter blues or satisfy your saltwater craving, this bright and airy 1-bedroom, ...

    From $308 per night (USD)

    Expedia

    Details
  • Magnificent gulf front condo with beautiful white sand beach
    From $123 per night (USD)

    VRBO

    Magnificent gulf front condo with beautiful white sand beach

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Magnificent direct Gulf front property on Longboat Key. The condo has been updated from furniture and furnishings to pai ...

    From $123 per night (USD)

    VRBO

    Details
  • Beachplace 5-301 Condo by RVA
    From $239 per night (USD)

    Expedia

    Beachplace 5-301 Condo by RVA

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    RVA proudly presents an exquisite two-bedroom, two-bathroom residence nestled in building 5, offering unparalleled Gulf ...

    From $239 per night (USD)

    Expedia

    Details
  • Gorgeous Full Gulf Front Condo.
    From $408 per night (USD)

    VRBO

    Gorgeous Full Gulf Front Condo.

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Coastal Contemporary Condo located at the Sea Gate complex on south Longboat Key. Corner unit on the fourth floor. Co ...

    From $408 per night (USD)

    VRBO

    Details
  • Beachy One-Bedroom on the Coast!
    From $478 per night (USD)

    Expedia

    Beachy One-Bedroom on the Coast!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    This charming seaside condo is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in excl ...

    From $478 per night (USD)

    Expedia

    Details
  • Bayport Beach & Tennis Club ~ A Beach to Bay Tropical Oasis!
    From $199 per night (USD)

    VRBO

    Bayport Beach & Tennis Club ~ A Beach to Bay Tropical Oasis!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to Bayport Beach and Tennis Club! Bayport Beach and Tennis Club is a beach to bay tropical oasis situated on 27 ...

    From $199 per night (USD)

    VRBO

    Details
  • Cedars East #804 Townhome by RVA
    From $335 per night (USD)

    Expedia

    Cedars East #804 Townhome by RVA

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    4

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

    From $335 per night (USD)

    Expedia

    Details
  • Private townhome steps from the beach and right next to the pool
    From $207 per night (USD)

    VRBO

    Private townhome steps from the beach and right next to the pool

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    9

    Beautiful 2 story private townhome has been recently updated in a bohemian beach vibe with warm pinks, blues and greens ...

    From $207 per night (USD)

    VRBO

    Details
  • Paradise!  Gulf beach, On bay, bike, fish, kayak, relax, shop, swim, tennis.....
    From $142 per night (USD)

    Expedia

    Paradise! Gulf beach, On bay, bike, fish, kayak, relax, shop, swim, tennis.....

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Beautiful condo located on 2nd floor. End unit overlooking beautiful tropical plants and offering natural light ! Turn ...

    From $142 per night (USD)

    Expedia

    Details
  • Beachplace 11-303 Condo by RVA
    From $222 per night (USD)

    VRBO

    Beachplace 11-303 Condo by RVA

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    RVA offers this comfortably appointed two-bedroom, two-bathroom condominium in the desirable gated community of Beachpla ...

    From $222 per night (USD)

    VRBO

    Details
  • Private home, North End LBK. 2 Bedrooms 1 Bath On 2nd Floor NO HURRICANE DAMAGE
    From $188 per night (USD)

    Expedia

    Private home, North End LBK. 2 Bedrooms 1 Bath On 2nd Floor NO HURRICANE DAMAGE

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Private Beach Cottage with apartment on second floor. Top floor apartment has two bedrooms, one bath, Living Room and Ea ...

    From $188 per night (USD)

    Expedia

    Details
  • Best views of the beach from your balcony Unit 301
    From $399 per night (USD)

    VRBO

    Best views of the beach from your balcony Unit 301

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to Paradise! Unit 301 with unobstructed Mexican Gulf View. This is a corner condo, so you have more space and a ...

    From $399 per night (USD)

    VRBO

    Details
  • ⚓The Tree House! Beautiful townhome in Longboat Key with great amenities surrounded by nature!⚓
    From $306 per night (USD)

    Expedia

    ⚓The Tree House! Beautiful townhome in Longboat Key with great amenities surrounded by nature!⚓

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to The Tree House in Cedars East Longboat Key! ⚓Short bike ride to beaches ⚓Community Pool, Kayak Launch, Natur ...

    From $306 per night (USD)

    Expedia

    Details
  • PENTHOUSE WITH A SPECTACULAR VIEWS OF THE GULF OF MEXICO EQUALY SARASOTA BAY
    Click For Pricing

    VRBO

    PENTHOUSE WITH A SPECTACULAR VIEWS OF THE GULF OF MEXICO EQUALY SARASOTA BAY

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    4

    Penthouse Contemporary design. Spectacular Views of Gulf & Sarasota Bay. Kitchen, Self Clean Oven, Micro, Dishwasher. Sp ...

    Click For Pricing

    VRBO

    Details
  • Cedars East #603 Townhome by RVA
    From $303 per night (USD)

    Expedia

    Cedars East #603 Townhome 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 $303 per night (USD)

    Expedia

    Details
  • Arbomar 302 Gulf Front 2 BR by FVC
    From $307 per night (USD)

    VRBO

    Arbomar 302 Gulf Front 2 BR by FVC

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Beachfront Bliss on Longboat Key – Stunning Views & Modern Comfort Stay directly on the beach in this beautifully upd ...

    From $307 per night (USD)

    VRBO

    Details
  • Newly Renovated - 2BR Beachfront Condo by FVC
    From $214 per night (USD)

    Expedia

    Newly Renovated - 2BR Beachfront Condo by FVC

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    NEWLY RENOVATED!! A beachfront condominium managed by Florida Vacation Connection is located on the world-renowned Long ...

    From $214 per night (USD)

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  • Beachview 2 BR \/ 2 BA Beachplace condo by FVC
    From $221 per night (USD)

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    Beachview 2 BR \/ 2 BA Beachplace condo by FVC

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Offered by FL Vacation Connection, Beachplace is a wonderful community known for its beautifully manicured grounds, outs ...

    From $221 per night (USD)

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  • Experience a resort feel vacation on the beach in Longboat Key
    From $322 per night (USD)

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    Experience a resort feel vacation on the beach in Longboat Key

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Two bedrooms, two baths, (approximately 1500 square feet) with a study, two balconies, an assigned covered parking , loc ...

    From $322 per night (USD)

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  • Adorable condo with a full kitchen & outdoor space - just steps from the beach
    From $313 per night (USD)

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    Adorable condo with a full kitchen & outdoor space - just steps from the beach

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Gulf View Cottage #3 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...

    From $313 per night (USD)

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  • Unit #208 Sand Cay Beach Resort Pool and Garden View
    From $435 per night (USD)

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    Unit #208 Sand Cay Beach Resort Pool and Garden View

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Perfect for families, this vacation rental features flat screen TV's in every room, fine furnishings and everything you ...

    From $435 per night (USD)

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  • Beachplace 7-102 Condo by RVA
    From $352 per night (USD)

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    Beachplace 7-102 Condo by RVA

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to Beachplace 7-102, a nicely decorated two-bedroom, two-bath unit at Beachplace that includes direct, private w ...

    From $352 per night (USD)

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  • REMODELED!!! Enjoy a Taste of Paradise from an Oceanfront Condo on White Sands!
    From $326 per night (USD)

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    REMODELED!!! Enjoy a Taste of Paradise from an Oceanfront Condo on White Sands!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    This Beachplace condo, situated on the sands of Longboat Key, Florida, offers a breathtaking, panoramic view of the Gulf ...

    From $326 per night (USD)

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  • Beautiful, renovated Gulf Front at Sand Cay with private beach on Longboat
    From $612 per night (USD)

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    Beautiful, renovated Gulf Front at Sand Cay with private beach on Longboat

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Your safety is our top priority. This unit is professionally cleaned using EPA registered product to combat Covid-19. In ...

    From $612 per night (USD)

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  • ON the Beach, 2nd Floor - Elevator - Heated swimming pool and Spa
    From $402 per night (USD)

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    ON the Beach, 2nd Floor - Elevator - Heated swimming pool and Spa

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    On the Beach - Full view of the Gulf of Mexico. Fully furnished and equipped. Includes Long Distance phone service wit ...

    From $402 per night (USD)

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  • \Discover Your Coastal Oasis  in Longboat Key, FL\  and St. Armands Area
    From $320 per night (USD)

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    \"Discover Your Coastal Oasis in Longboat Key, FL\" and St. Armands Area

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Stunning one bedroom one bath unit with just a short walk to Longboat Key Beach(Across the Street). Come enjoy beautiful ...

    From $320 per night (USD)

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  • La Playa #203D Luxury Condo by RVA
    From $778 per night (USD)

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    La Playa #203D Luxury Condo by RVA

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to La Playa #203D by RVA. Step out your door to the white sandy beach and emerald waters of the Gulf of Mexico. ...

    From $778 per night (USD)

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  • Beautiful 2\/2 bay veiw unit!! Fall dates are filling up quick, book yours today!
    From $238 per night (USD)

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    Beautiful 2\/2 bay veiw unit!! Fall dates are filling up quick, book yours today!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Come enjoy some peace in quiet in beautiful Longboat Key. This clean and comfortable 2 bedroom 2 bathroom condo on Saras ...

    From $238 per night (USD)

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  • Take a Peek at a fabulous unit.
    From $361 per night (USD)

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    Take a Peek at a fabulous unit.

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    6

    This property is a family-owned 800 square foot tower apartment on the shores of the Gulf of Mexico. There is a full ki ...

    From $361 per night (USD)

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  • Client texted view crazy see for yourself
    From $361 per night (USD)

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    Client texted view crazy see for yourself

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    6

    This property is a family-owned 800 square foot tower apartment on the shores of the Gulf of Mexico. There is a full ki ...

    From $361 per night (USD)

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  • 🏝Tropical, Private, Gated Home w\/ pool Short Walk to St Armands & Lido & LBK🏖
    From $618 per night (USD)

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    🏝Tropical, Private, Gated Home w\/ pool Short Walk to St Armands & Lido & LBK🏖

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Lido Key is located off the coast of downtown Sarasota and directly across the cascading Ringling Causeway. Sarasota's n ...

    From $618 per night (USD)

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  • Gulf Front, luxury condominium in beautiful Long Boat Key, FL
    From $196 per night (USD)

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    Gulf Front, luxury condominium in beautiful Long Boat Key, FL

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Prime location and luxury !!!! Enjoy spectacular sunsets and incredible water views of the Gulf of Mexico in this upscal ...

    From $196 per night (USD)

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  • Lido Beach  Corner of Beach and St. Armand Circle B
    From $131 per night (USD)

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    Lido Beach Corner of Beach and St. Armand Circle B

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Perfect Beach Location. Right across from Lido Beach and immediatly next to St. Armands Circle. Walk to the many resta ...

    From $131 per night (USD)

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  • THE BEACH CONDO #107.  DIRECLY ON GULF FULL VIEW
    From $433 per night (USD)

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    THE BEACH CONDO #107. DIRECLY ON GULF FULL VIEW

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Studio, sleeps 4, full kitchen with ss appliances and granite countertops, 1 ba, private beach front patio, heated beach ...

    From $433 per night (USD)

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  • Stunning sunset views; Beachfront condo on central Longboat Key
    From $405 per night (USD)

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    Stunning sunset views; Beachfront condo on central Longboat Key

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Private Condo located on second floor at Tiffany Plaza on Longboat Key. Second floor accessible only by security code el ...

    From $405 per night (USD)

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  • Ocean View Large Lido Beach  Corner of Beach and St. Armand Circle A
    From $129 per night (USD)

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    Ocean View Large Lido Beach Corner of Beach and St. Armand Circle A

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    2BR, Comfortable King size bed in the master bedroom and Queen size bed in the 2nd bedroom Shower/bath. Stove microwave, ...

    From $129 per night (USD)

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  • Turtle Crawl Inn
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    Turtle Crawl Inn

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    <p>While you're here, you can enjoy all the comforts of home and more, including free WiFi and an LED TV, as well as a c ...

    Click For Pricing

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    Details
  • Your Vacation Oasis Awaits on Beautiful Longboat Key!
    From $372 per night (USD)

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    Your Vacation Oasis Awaits on Beautiful Longboat Key!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    3 Bed, 3 Bath recently renovated Beach house with large sun deck and heated pool surrounded by beautiful landscaping tha ...

    From $372 per night (USD)

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  • Delightful 2\/2 Beach House LBK 5 Min walk to Beach
    From $163 per night (USD)

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

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    5

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

    From $163 per night (USD)

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  • NO REGRETS -Bright beautiful sunny home. Elevator beside driveway to upstairs.
    From $571 per night (USD)

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    NO REGRETS -Bright beautiful sunny home. Elevator beside driveway to upstairs.

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    8

    We have a private laneway to our own piece of beautiful sugar sand, longboat key beach. We adjoin 35 acres of park and ...

    From $571 per night (USD)

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  • Cabana Beach Club #2 Resort by RVA
    From $470 per night (USD)

    Expedia

    Cabana Beach Club #2 Resort by RVA

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    RVA features Cabana Beach Club. With the majority of units located on the beach side of the exclusive Longboat Key islan ...

    From $470 per night (USD)

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  • Casa Del Mar Home on Longboat Key by RVA
    From $466 per night (USD)

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    Casa Del Mar Home on Longboat Key by RVA

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Enjoy island-style vacations at the Casa del Mar Home. Located on the north end of the exclusive island of Longboat Key, ...

    From $466 per night (USD)

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  • Cedars East #528 Townhome by RVA
    From $319 per night (USD)

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    Cedars East #528 Townhome by RVA

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    6

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

    From $319 per night (USD)

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  • Silver Sands #234 Resort by RVA
    From $216 per night (USD)

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    Silver Sands #234 Resort by RVA

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

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

    From $216 per night (USD)

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  • Walk to Beach\/Bay, 1st Floor, Beach Castle #23
    From $378 per night (USD)

    Expedia

    Walk to Beach\/Bay, 1st Floor, Beach Castle #23

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Relax in this privately owned and “coastal themed” ground floor condo that sleeps 4 with bay views from the privacy of y ...

    From $378 per night (USD)

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  • Silver Sands #245 Resort by RVA
    From $308 per night (USD)

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    Silver Sands #245 Resort by RVA

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

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

    From $308 per night (USD)

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  • Silver Sands #241A Resort by RVA
    From $296 per night (USD)

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    Silver Sands #241A Resort by RVA

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

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

    From $296 per night (USD)

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  • Tarawitt Home on Longboat Key by RVA
    From $275 per night (USD)

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    Tarawitt Home on Longboat Key by RVA

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    RVA presents this spacious vacation home. The Tarawitt Home, is located on a secluded road at the northern tip of Longbo ...

    From $275 per night (USD)

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  • Island Paradise: House on Longboat Key by RVA
    From $265 per night (USD)

    Expedia

    Island Paradise: House on Longboat Key by RVA

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    RVA features a relaxing, serene home beautifully furnished and ready for you to enjoy Longboat Key's sunshine. This home ...

    From $265 per night (USD)

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  • Silver Sands #252 Resort by RVA
    From $346 per night (USD)

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    Silver Sands #252 Resort by RVA

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

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

    From $346 per night (USD)

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  • St. Armands oasis with saltwater pool - walk to beach & shops
    From $546 per night (USD)

    Expedia

    St. Armands oasis with saltwater pool - walk to beach & shops

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Anything Is Possible Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...

    From $546 per night (USD)

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    Details
  • Huge Home with Pool, Home Office, & Sunroom | Walk to Lido Beach
    From $755 per night (USD)

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    Huge Home with Pool, Home Office, & Sunroom | Walk to Lido Beach

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    8

    You Only Live Once Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...

    From $755 per night (USD)

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  • Silver Sands #255S Resort by RVA
    From $479 per night (USD)

    Expedia

    Silver Sands #255S Resort by RVA

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

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

    From $479 per night (USD)

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    Details
  • Beach Castle Resort #1 by RVA
    From $496 per night (USD)

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    Beach Castle Resort #1 by RVA

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Compliments of RVA, Beach Castle Resort expands from the bayside of Longboat Key to the Gulf – providing a place to laun ...

    From $496 per night (USD)

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  • Silver Sands #235 Resort by RVA
    From $479 per night (USD)

    Expedia

    Silver Sands #235 Resort by RVA

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

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

    From $479 per night (USD)

    Expedia

    Details
  • Cabana Beach Club #7 Resort by RVA
    From $417 per night (USD)

    VRBO

    Cabana Beach Club #7 Resort by RVA

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    RVA features Cabana Beach Club. With the majority of units located on the beach side of the exclusive Longboat Key islan ...

    From $417 per night (USD)

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    Details
  • Silver Sands #241 Resort by RVA
    From $301 per night (USD)

    Expedia

    Silver Sands #241 Resort by RVA

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

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

    From $301 per night (USD)

    Expedia

    Details