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Results: 648 Rentals

  • Cozy Cedars East Townhome #622 by RVA
    From $295 per night (USD)

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    Cozy Cedars East Townhome #622 by RVA

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Escape to Paradise at Cedars East Tennis Resort by RVA Resort Vacations. Discover the ultimate Longboat Key getaway at ...

    From $295 per night (USD)

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  • Silver Sands 1BR – Gulfside Comfort #255 by RVA
    From $385 per night (USD)

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    Silver Sands 1BR – Gulfside Comfort #255 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 $385 per night (USD)

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  • 2nd Floor Retreat – Silver Sands #251 by RVA
    From $375 per night (USD)

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    2nd Floor Retreat – Silver Sands #251 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 $375 per night (USD)

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  • Cedars East Bayview Tennis & Pool Unit 822 by RVA
    From $316 per night (USD)

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    Cedars East Bayview Tennis & Pool Unit 822 by RVA

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Discover the ultimate Longboat Key getaway at Cedars Tennis Resort, where luxury living meets the beauty of Florida’s Gu ...

    From $316 per night (USD)

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  • Charming Beach Condo – Silver Sands Resort #240 by RVA
    From $430 per night (USD)

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    Charming Beach Condo – Silver Sands Resort #240 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 $430 per night (USD)

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  • Relax & Play – Cedars East 2BR #850 RVA
    From $394 per night (USD)

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    Relax & Play – Cedars East 2BR #850 RVA

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Escape to Paradise at Cedars East Tennis Resort by RVA Resort Vacations. Discover the ultimate Longboat Key getaway at ...

    From $394 per night (USD)

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  • Gulf Coast Getaway–Cedars East Tennis #509/RVA
    From $251 per night (USD)

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    Gulf Coast Getaway–Cedars East Tennis #509/RVA

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Escape to Paradise at Cedars East Tennis Resort by RVA Resort Vacations. Discover the ultimate Longboat Key getaway at ...

    From $251 per night (USD)

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  • Beachfront Longboat Key Outrigger #7 by RVA
    From $399 per night (USD)

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    Beachfront Longboat Key Outrigger #7 by RVA

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    RVA features a narrow footpath through the native scenery leads you to the private Gulf of Mexico beach at the Outrigger ...

    From $399 per night (USD)

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  • Silver Sands #245S Resort by RVA
    From $558 per night (USD)

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    Silver Sands #245S 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 $558 per night (USD)

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  • Cozy Beach Studio – Silver Sands #251A by RVA
    From $329 per night (USD)

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    Cozy Beach Studio – Silver Sands #251A 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 $329 per night (USD)

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  • Beach & Tennis Paradise–Cedars East #806 by RVA
    From $329 per night (USD)

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    Beach & Tennis Paradise–Cedars East #806 by RVA

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Escape to Paradise at Cedars East Tennis Resort by RVA Resort Vacations. Discover the ultimate Longboat Key getaway at ...

    From $329 per night (USD)

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  • Elegance Meets Ocean – Silver Sands #248 by RVA
    From $430 per night (USD)

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    Elegance Meets Ocean – Silver Sands #248 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 $430 per night (USD)

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  • Courtside Getaway – Cedars East #605 by RVA
    From $329 per night (USD)

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    Courtside Getaway – Cedars East #605 by RVA

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Escape to Paradise at Cedars East Tennis Resort by RVA Resort Vacations. Discover the ultimate Longboat Key getaway at ...

    From $329 per night (USD)

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  • Direct Beach Access – Silver Sands #249 by RVA
    From $627 per night (USD)

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    Direct Beach Access – Silver Sands #249 by RVA

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    7

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

    From $627 per night (USD)

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  • 2nd-Floor Gulffront Outrigger #6 Condo by RVA
    From $383 per night (USD)

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    2nd-Floor Gulffront Outrigger #6 Condo by RVA

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    RVA features a narrow footpath through the native scenery leads you to the private Gulf of Mexico beach at the Outrigger ...

    From $383 per night (USD)

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  • Beach Bungalow: Best Canal, Dock, Beach, Pool, Pet Friendly. Renovated in 2025
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    Beach Bungalow: Best Canal, Dock, Beach, Pool, Pet Friendly. Renovated in 2025

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    This beautiful and spacious 3 bedroom house underwent a total renovation in 2025, it's brand new. Located on one of the ...

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  • 1st Floor 2 Bed 1 bath home, short walk to beach, 1 step to door, North end LBK
    From $221 per night (USD)

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    1st Floor 2 Bed 1 bath home, short walk to beach, 1 step to door, North end LBK

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Private Beach Cottage ground floor apartment. This ground floor apartment has two bedrooms, one bath, Living Room and ...

    From $221 per night (USD)

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  • Unit #318 Sand Cay Beach Resort Gulf Front
    From $588 per night (USD)

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    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 $588 per night (USD)

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  • Coastal Elegance 3BR w Private Balcony, Pool & Direct Gulf Access by RVA
    From $368 per night (USD)

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    Coastal Elegance 3BR w Private Balcony, Pool & Direct Gulf Access by RVA

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    5

    RVA welcomes you to Villas of Avignon - where you can enjoy a secluded beach, heated community pool, private balconies a ...

    From $368 per night (USD)

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  • Bayside 2BR on Whitney Beach w Canal Views, Pool, and Private Lanai  by RVA
    From $241 per night (USD)

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    Bayside 2BR on Whitney Beach w Canal Views, Pool, and Private Lanai by RVA

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

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

    From $241 per night (USD)

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  • Sunset and beach view from your balcony Unit 403
    From $507 per night (USD)

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    Sunset and beach view from your balcony Unit 403

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    6

    A luxurious beachfront experience awaits you on the beautiful white sands and emerald waters of the Gulf of Mexico when ...

    From $507 per night (USD)

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  • Beachside at Whitney Beach: 2BR Ground-Floor Condo w Gulf Views & Pool by RVA
    From $249 per night (USD)

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    Beachside at Whitney Beach: 2BR Ground-Floor Condo w Gulf Views & Pool by RVA

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

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

    From $249 per night (USD)

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  • Island Time: Open Sept 13th - 16th!
    From $426 per night (USD)

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    Island Time: Open Sept 13th - 16th!

    Bedrooms:
    1
    Bathrooms:
    0
    Sleeps:
    4

    This sublime oceanfront studio is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in e ...

    From $426 per night (USD)

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  • DOG FRIENDLY and PERFECT LBK LOCATION
    From $424 per night (USD)

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    DOG FRIENDLY and PERFECT LBK LOCATION

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    *Calendar not always updated. Messege me for specific dates. Newly ren ...

    From $424 per night (USD)

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  • 3 BEDROOM DIRECT OCEAN VIEW, WALKOUT TO THE BEACH!
    From $939 per night (USD)

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    3 BEDROOM DIRECT OCEAN VIEW, WALKOUT TO THE BEACH!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Priority for inquiries bundling Jan AND Feb TOGETHER. No half months please. February alone is not available. FULL WA ...

    From $939 per night (USD)

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  • Beachcomber unit 403
    From $320 per night (USD)

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    Beachcomber unit 403

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Our building is located on the beach, this unit has an ISLAND view. Beach front units are available to rese ...

    From $320 per night (USD)

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  • Beachcomber unit 405
    From $321 per night (USD)

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    Beachcomber unit 405

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Our building is located on the beach, this unit has an ISLAND view. Beach front units are available to rese ...

    From $321 per night (USD)

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  • Beachcomber unit 203
    From $320 per night (USD)

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    Beachcomber unit 203

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Newly Refreshed Beach Condo - Unit 203 Welcome to our beautifully redesigned and refreshed condo. In Novemb ...

    From $320 per night (USD)

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  • Beachcomber unit 303
    From $323 per night (USD)

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    Beachcomber unit 303

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Our building is located on the beach, this unit has an ISLAND view. Enjoy upscale Longboat Key in the elega ...

    From $323 per night (USD)

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  • Beachcomber unit 204
    From $496 per night (USD)

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    Beachcomber unit 204

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    This is a great location directly on the beach with a spectacular view of the Gulf of Mexico. This Gulf fro ...

    From $496 per night (USD)

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  • Beachcomber unit 305
    From $323 per night (USD)

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    Beachcomber unit 305

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Our building is located on the beach, this unit has an ISLAND view. Pack your bags, invite your family and ...

    From $323 per night (USD)

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  • Longboat Key Luxury Condo - walking to St. Armand's Circle!
    From $702 per night (USD)

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

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    4

    This luxurious COVID free top floor end unit condo was newly furnished in 2022 and features an elevator. Taking in v ...

    From $702 per night (USD)

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  • Canal Front Home - 8 min walk to beach.  RRR-00953.2023
    From $815 per night (USD)

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    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 $815 per night (USD)

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  • Longboat Key Beachfront Incredible 2/2 Postcard Sunsets
    From $257 per night (USD)

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    Longboat Key Beachfront Incredible 2/2 Postcard Sunsets

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Enjoy beachfront living, captivating ocean views, spectacular sunsets and balcony access from every room. Wake up each m ...

    From $257 per night (USD)

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  • 7th Heaven by Duncan Real Estate
    From $396 per night (USD)

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    7th Heaven by Duncan Real Estate

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Welcome to 7th Heaven on beautiful Longboat Key! A beachfront escape directly on the Gulf of Mexico with views of turquo ...

    From $396 per night (USD)

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  • Country Club Long Boat Key Beach Villa  2B 3BA Pool
    From $273 per night (USD)

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    Country Club Long Boat Key Beach Villa 2B 3BA Pool

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Longboat Key Rental Registry Number: RRR-01566.2026 Villa is 15 steps from your own private sugar sand bay beach. Ced ...

    From $273 per night (USD)

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  • Beachcomber unit 202
    From $496 per night (USD)

    VRBO

    Beachcomber unit 202

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Staying on Longboat Key means you get to experience what Heaven on Earth feels like. A place where you can walk on prist ...

    From $496 per night (USD)

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  • Beachcomber unit 501
    From $320 per night (USD)

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    Beachcomber unit 501

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Our building is located on the beach, this unit has an ISLAND view. Relax and Enjoy the Beach, Pool & Longb ...

    From $320 per night (USD)

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  • Beachcomber unit 201
    From $320 per night (USD)

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    Beachcomber unit 201

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Our building is located on the beach, this unit has an ISLAND view. Welcome Snow Birds and Florida locals l ...

    From $320 per night (USD)

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  • Unit #114 Sand Cay Beach Resort Pool View
    From $491 per night (USD)

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    Unit #114 Sand Cay Beach Resort Pool View

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Our resort has a relaxed, upscale feel. It is great for vacationers seeking peace and tranquility as well as families wa ...

    From $491 per night (USD)

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  • Unit #203 Sand Cay Beach Resort Gulf Front
    From $545 per night (USD)

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    Unit #203 Sand Cay Beach Resort Gulf Front

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Second Floor, non-smoking unit. Best views to the beach/Gulf in the Sand Cay complex. Three large bay windows looki ...

    From $545 per night (USD)

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  • Unit #204 Sand Cay Beach Resort Gulf Front
    From $588 per night (USD)

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    Unit #204 Sand Cay Beach Resort Gulf Front

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Second floor non-smoking unit. Accommodates 6 people. Living room has a 110" window with a direct view of the beach/Gu ...

    From $588 per night (USD)

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  • Unit #111 Sand Cay Beach Resort Pool View
    From $495 per night (USD)

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    Unit #111 Sand Cay Beach Resort Pool View

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Come experience the ultimate white sandy private beach front boutique Florida paradise. When planning a trip to the beau ...

    From $495 per night (USD)

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  • Unit #106 Sand Cay Beach Resort Gulf View
    From $534 per night (USD)

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    Unit #106 Sand Cay Beach Resort Gulf View

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Bright, beachy ground floor unit with a lovely view and easy access of the Gulf. Large, extended bedrooms that comforta ...

    From $534 per night (USD)

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  • Unit #201 Sand Cay Beach Resort Gulf View
    From $534 per night (USD)

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    Unit #201 Sand Cay Beach Resort Gulf View

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Quaint, quiet, and the quality of a boutique resort, not the hassle, noise, the impersonal nature of a hotel. You will b ...

    From $534 per night (USD)

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  • Unit #209 Sand Cay Beach Resort Pool View
    From $495 per night (USD)

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    Unit #209 Sand Cay Beach Resort Pool View

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Just a short walk to the beach, and steps away from the office, fenced in pool, tennis court and laundry facilities. Th ...

    From $495 per night (USD)

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  • Unit #303 Sand Cay Beach Resort Gulf Front
    From $588 per night (USD)

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    Unit #303 Sand Cay Beach Resort Gulf Front

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to paradise! Now is a great time to escape to the beach where you can destress in an environment that makes it e ...

    From $588 per night (USD)

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  • Unit #120 Sand Cay Beach Resort Gulf View
    From $492 per night (USD)

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    Unit #120 Sand Cay Beach Resort Gulf View

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Beach Front Condo That Has It All Wonderful ground floor unit – walk right to the beach – no steps to deal with! Very p ...

    From $492 per night (USD)

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  • Unit #320 Sand Cay Beach Resort Gulf Front
    From $588 per night (USD)

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    Unit #320 Sand Cay Beach Resort Gulf Front

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Master bedroom has king size bed and full bath. Second bedroom has twin beds with full bath. Extremely well equipped k ...

    From $588 per night (USD)

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  • Unit #105 Sand Cay Beach Resort Gulf View
    From $494 per night (USD)

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    Unit #105 Sand Cay Beach Resort Gulf View

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Just like Longboat Key’s original tourists, residents and visitors alike enjoy the beaches and weather — but today’s isl ...

    From $494 per night (USD)

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  • Unit #205 Sand Cay Beach Resort  Gulf View
    From $534 per night (USD)

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    Unit #205 Sand Cay Beach Resort Gulf View

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Experience spectacular views from this beautifully appointed and well-located Gulf View (Close to Gulf Front) unit! Now ...

    From $534 per night (USD)

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  • Unit #104 Sand Cay Beach Resort Gulf Front
    From $551 per night (USD)

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    Unit #104 Sand Cay Beach Resort Gulf Front

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Just like Longboat Key’s original tourists, residents and visitors alike enjoy the beaches and weather — but today’s isl ...

    From $551 per night (USD)

    Expedia

    Details
  • Unit #107 Sand Cay Beach Resort Pool View
    From $495 per night (USD)

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    Unit #107 Sand Cay Beach Resort Pool View

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Just like Longboat Key’s original tourists, residents and visitors alike enjoy the beaches and weather — but today’s isl ...

    From $495 per night (USD)

    VRBO

    Details
  • Unit #116 Sand Cay Beach Resort Gulf Front
    From $551 per night (USD)

    Expedia

    Unit #116 Sand Cay Beach Resort Gulf Front

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    First floor Gulf front. King bed in the master, Two full beds in guest bedroom. The bedrooms are extended adding extra s ...

    From $551 per night (USD)

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  • Unit #311 Sand Cay Beach Resort Pool View
    From $495 per night (USD)

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    Unit #311 Sand Cay Beach Resort Pool View

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Third floor unit looks over the heated pool of Sand Cay. Decorated unit has all the luxuries of home. Quaint, quiet, an ...

    From $495 per night (USD)

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    Details
  • Unit #219 Sand Cay Beach Resort Gulf Front
    From $545 per night (USD)

    Expedia

    Unit #219 Sand Cay Beach Resort Gulf Front

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    All new appliances, granite and walk-in master shower. Living space has a Hi def flat-screen TV. Comfortable and cozy, ...

    From $545 per night (USD)

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    Details
  • Unit #217 Sand Cay Beach Resort Gulf Front
    From $588 per night (USD)

    VRBO

    Unit #217 Sand Cay Beach Resort Gulf Front

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Second floor, The kitchen/living room was renovated / furnished in 2017. All new bathrooms and bedrooms renovated in 20 ...

    From $588 per night (USD)

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    Details
  • Unit #117 Sand Cay Beach Resort Gulf Front
    From $551 per night (USD)

    Expedia

    Unit #117 Sand Cay Beach Resort Gulf Front

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Beachfront, Beachfront, Beachfront! You cannot get any closer to the beach! Just walk out your patio and your toes are i ...

    From $551 per night (USD)

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    Details
  • Unit #306 Sand Cay Beach Resort Gulf View
    From $492 per night (USD)

    VRBO

    Unit #306 Sand Cay Beach Resort Gulf View

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Third floor,. Living room and master bedroom has new furniture. Murphy bed in living room. Quaint, quiet, and the qualit ...

    From $492 per night (USD)

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    Details
  • Unit #315 Sand Cay Beach Resort Gulf View
    From $534 per night (USD)

    Expedia

    Unit #315 Sand Cay Beach Resort Gulf View

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    #315 is a beautiful, light, bright, spacious 2 Bedroom 2 Bath 3rd Floor Condominium with gorgeous views of the Gulf of M ...

    From $534 per night (USD)

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  • Unit #301 Sand Cay Beach Resort Gulf View 7 Night Minimum
    From $492 per night (USD)

    VRBO

    Unit #301 Sand Cay Beach Resort Gulf View 7 Night Minimum

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to our totally renovated home. Located on the top floor of building 4 next to 11 lovely quiet condominiums. You ...

    From $492 per night (USD)

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    Details
  • Unit #307 Sand Cay Beach Resort Pool View
    From $453 per night (USD)

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    Unit #307 Sand Cay Beach Resort Pool View

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Bright and sunny two-bedroom two-bathroom condo in a small resort located on the beach. Top floor unit with elevator acc ...

    From $453 per night (USD)

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    Details
  • Unit #216 Sand Cay Beach Resort Gulf Front
    From $551 per night (USD)

    VRBO

    Unit #216 Sand Cay Beach Resort Gulf Front

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Breathtaking Gulf front views awaits, salt life could not be better! Enjoy spectacular sunset views, steps from the beac ...

    From $551 per night (USD)

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  • Unit #215 Sand Cay Beach Resort Gulf View
    From $492 per night (USD)

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    Unit #215 Sand Cay Beach Resort Gulf View

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Stunning Gulf-Front Condo-Fully Renovated-Sleeps 6-Sunset Views Enjoy breathtaking sunsets from this beautifully renova ...

    From $492 per night (USD)

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  • Unit #118 Sand Cay Beach Resort Gulf Front
    From $588 per night (USD)

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    Unit #118 Sand Cay Beach Resort Gulf Front

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Just like Longboat Key’s original tourists, residents and visitors alike enjoy the beaches and weather — but today’s isl ...

    From $588 per night (USD)

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  • Unit #109 Sand Cay Beach Resort Pool View
    From $490 per night (USD)

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    Unit #109 Sand Cay Beach Resort Pool View

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Just like Longboat Key’s original tourists, residents and visitors alike enjoy the beaches and weather — but today’s isl ...

    From $490 per night (USD)

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  • Unit #108 Sand Cay Beach Resort Pool View
    From $453 per night (USD)

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    Unit #108 Sand Cay Beach Resort Pool View

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    This sought after, BEAUTIFULLY FURNISHED, two bedrooms, two bath FIRST FLOOR END UNIT offers fully renovated kitchen an ...

    From $453 per night (USD)

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  • Unit #316 Sand Cay Beach Resort Gulf Front
    From $588 per night (USD)

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    Unit #316 Sand Cay Beach Resort Gulf Front

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Unit can accommodate up to six people with the sleeper sofa in living room. This unit is a must rent for a first class ...

    From $588 per night (USD)

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  • Unit #113 Sand Cay Beach Resort Pool View
    From $490 per night (USD)

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    Unit #113 Sand Cay Beach Resort Pool View

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Extended bedrooms. Amenities include 3 televisions with DVD and washer and dryer. Quaint, quiet, and the quality of a bo ...

    From $490 per night (USD)

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  • Unit #314 Sand Cay Beach Resort Pool View
    From $495 per night (USD)

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    Unit #314 Sand Cay Beach Resort Pool View

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Light and bright, close to the elevator, this third floor condo is garden view, midway between the pool and beach. The ...

    From $495 per night (USD)

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  • Unit #103 Sand Cay Beach Resort Gulf Front
    From $588 per night (USD)

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    Unit #103 Sand Cay Beach Resort Gulf Front

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Unit 103 is completely renovated, stylish and modern in hues of grey, black and white, complemented by all new furnishin ...

    From $588 per night (USD)

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  • Unit #110 Sand Cay Beach  Pool View
    From $450 per night (USD)

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    Unit #110 Sand Cay Beach Pool View

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Perfect for families! First floor by the pool with "Private Front Yard" landscaping. View of the Gulf of Mexico from li ...

    From $450 per night (USD)

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  • Unit #304 Sand Cay Beach Resort Gulf Front
    From $971 per night (USD)

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    Unit #304 Sand Cay Beach Resort Gulf Front

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Great family unit features spectacular views of the Gulf of Mexico & and the property's lovely garden. Quaint, quiet, a ...

    From $971 per night (USD)

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  • Unit #115 Sand Cay Beach Resort Gulf View
    From $481 per night (USD)

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    Unit #115 Sand Cay Beach Resort Gulf View

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    All new floors, bathrooms, kitchen, furniture, mattresses, appliances and more. Brand new open layout., including a firs ...

    From $481 per night (USD)

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  • Unit #102  Sand Cay Beach Resort Gulf Front
    From $588 per night (USD)

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    Unit #102 Sand Cay Beach Resort Gulf Front

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    First floor Gulf Front. Extended bedrooms. Recently redecorated. Private and very near Gulf. The kitchen is elegant ...

    From $588 per night (USD)

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  • Unit #312 Sand Cay Beach Resort Pool View
    From $490 per night (USD)

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    Unit #312 Sand Cay Beach Resort Pool View

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Third floor,, with balcony and View of Gulf, unit. Must see! Open living room with vaulted ceilings. Light and brightl ...

    From $490 per night (USD)

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  • Unit #305 Sand Cay Beach Resort Gulf View
    From $492 per night (USD)

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    Unit #305 Sand Cay Beach Resort Gulf View

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Light and elegant, third floor with high ceiling and Bay windows, non-smoking unit. Open kitchen, newly renovated baths, ...

    From $492 per night (USD)

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  • Unit #317 Sand Cay Beach Resort Gulf Front 7 night minimum
    From $533 per night (USD)

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    Unit #317 Sand Cay Beach Resort Gulf Front 7 night minimum

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    No walls interrupt panoramic gulf views in this beautifully renovated condo. With soaring ceilings and tiled floors, th ...

    From $533 per night (USD)

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  • Direct Beachfront Gulf with Amazing Views
    From $671 per night (USD)

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    Direct Beachfront Gulf with Amazing Views

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    LongBoat Key wins Conde Nast Traveler Award _______________________________________ **Our unit has its own Full sized ...

    From $671 per night (USD)

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  • Stunning -late summer sale 50 ft from sand, Private Island 125 +review
    From $543 per night (USD)

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    Stunning -late summer sale 50 ft from sand, Private Island 125 +review

    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 $543 per night (USD)

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  •  1  of a kind home 13 steps to sand LATE SUMMER SALE
    From $812 per night (USD)

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    1 of a kind home 13 steps to sand LATE SUMMER SALE

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Welcome to the Zilli family Villa beach house on Longboat Key. After using this 2,000 sf home for their own family vacat ...

    From $812 per night (USD)

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  • 3/2 Direct Beachfront Condo, Pool, Fitness, Tennis
    From $478 per night (USD)

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    3/2 Direct Beachfront Condo, Pool, Fitness, Tennis

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Beachplace Condo: A 3-Bedroom Modern Oasis on Longboat Key by FVC Step into the epitome of modern beachfront living wit ...

    From $478 per night (USD)

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  • Longboat Key Cedars Beach House-Pet Friendly-2 Minute Walk To The Beach
    From $218 per night (USD)

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    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 $218 per night (USD)

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  • Longboat Key Beachfront - Beautifully Updated with Prime Location
    From $412 per night (USD)

    VRBO

    Longboat Key Beachfront - Beautifully Updated with Prime Location

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Come enjoy this beautiful beachfront condo! Completely renovated and updated,, this condo is located at the desirable ...

    From $412 per night (USD)

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  •  End-of-summer sale  ready for a luxury   5-floor penthouse 60 ft from water,
    From $593 per night (USD)

    VRBO

    End-of-summer sale ready for a luxury 5-floor penthouse 60 ft from water,

    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. It is part of the ...

    From $593 per night (USD)

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  • Beachfront Villa on Serene Gulf of Mexico
    From $601 per night (USD)

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    Beachfront Villa on Serene Gulf of Mexico

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    LongBoat Key wins Conde Nast Traveler Award _______________________________________ **Unit has its own Full sized was ...

    From $601 per night (USD)

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  • Canal front home on Longboat Key -Just Steps to the Beach
    From $213 per night (USD)

    VRBO

    Canal front home on Longboat Key -Just Steps to the Beach

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Newly renovated and spacious canal-front home in beautiful Longboat Key with deeded beach access just steps down the str ...

    From $213 per night (USD)

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  • Peaceful Condo – Cedars East #803 by RVA
    From $302 per night (USD)

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    Peaceful Condo – Cedars East #803 by RVA

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Escape to Paradise at Cedars East Tennis Resort by RVA Resort Vacations. Discover the ultimate Longboat Key getaway at ...

    From $302 per night (USD)

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  • 1BR Beach Getaway – Silver Sands #254 by RVA
    From $375 per night (USD)

    VRBO

    1BR Beach Getaway – Silver Sands #254 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 $375 per night (USD)

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  • Gulf Views – Silver Sands #250, Longboat Key by RVA
    From $420 per night (USD)

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    Gulf Views – Silver Sands #250, Longboat Key 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 $420 per night (USD)

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  • Cozy condo in Cedars East
    From $216 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 $216 per night (USD)

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

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  • Beachcomber unit 504
    From $497 per night (USD)

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    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 $497 per night (USD)

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  • Dolphin’s Den: Seaside Escape w Rooftop Gulf Views & Private Beach by RVA
    From $423 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 $423 per night (USD)

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  • Beautiful private beach and backyard pool at our restored Old Florida house!
    From $332 per night (USD)

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    Beautiful private beach and backyard pool at our restored Old Florida house!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    4

    Beach cottage on a double lot with fenced yard on Long Boat Key Barrier Island. This 3 bedroom two full bath 50s ranch w ...

    From $332 per night (USD)

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  • BOOK NOW - BEAUTIFUL HOME NEAR BEACHES
    From $517 per night (USD)

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    BOOK NOW - BEAUTIFUL HOME NEAR BEACHES

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    12

    ISLAND PARADISE!!! Enjoy this spectacular home in a beautiful, very quiet, Longboat Key neighborhood. Enjoy the nearby p ...

    From $517 per night (USD)

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  • Gorgeous Gulf views and a beachfront location!
    From $416 per night (USD)

    VRBO

    Gorgeous Gulf views and a beachfront location!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    From the moment you walk in the door of this 2 1/2 bedroom, 2 bath beach front condo you will know you made the right ch ...

    From $416 per night (USD)

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  • Perfect cottage! Million dollar views
    From $207 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 $207 per night (USD)

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  • 2/2 Beachplace Condo, Beach, Pool, Fitness, Tennis
    From $254 per night (USD)

    VRBO

    2/2 Beachplace Condo, Beach, Pool, Fitness, Tennis

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Proudly offered by FL Vacation Connection, this property is ideal for professionals working remotely! Beautifully furn ...

    From $254 per night (USD)

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  • 2/2 Condo LBK, Pool, Fitness, Tennis
    From $195 per night (USD)

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    2/2 Condo LBK, Pool, Fitness, Tennis

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Offered by FL Vacation Connection, this fifth floor condo has views of the reflecting pond and fountain as well as a par ...

    From $195 per night (USD)

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