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Longboat Key Rentals

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  • Booking now for Spring 2023
    From $255 per night (USD)

    VRBO

    Booking now for Spring 2023

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    VRBO Welcomes you to a unique eight unit condominium. Nestled in the middle of Longboat Keys finest white sand beachs. ...

    From $255 per night (USD)

    VRBO

    Details
  • Oceanview Condo: Open May 30th, $125\/nt!
    From $150 per night (USD)

    Expedia

    Oceanview Condo: Open May 30th, $125\/nt!

    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 $150 per night (USD)

    Expedia

    Details
  • Beautiful Longboat home
    From $400 per night (USD)

    VRBO

    Beautiful Longboat home

    Bedrooms:
    4
    Bathrooms:
    3
    Sleeps:
    6

    Vacation in Paradise: Our Family has made our home the perfect vacation getaway. Perched on Sarasota Bay with spectac ...

    From $400 per night (USD)

    VRBO

    Details
  • DOG FRIENDLY and PERFECT LBK LOCATION
    From $268 per night (USD)

    Expedia

    DOG FRIENDLY and PERFECT LBK LOCATION

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

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

    From $268 per night (USD)

    Expedia

    Details
  • 3 BEDROOM DIRECT OCEAN VIEW, WALKOUT TO THE BEACH at Beachplace!
    From $575 per night (USD)

    VRBO

    3 BEDROOM DIRECT OCEAN VIEW, WALKOUT TO THE BEACH at Beachplace!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    FULL WALL-TO-WALL RENOVATION AND RE-IMAGINED 3 BEDROOM FLOOR PLAN 2021! FIRST FLOOR WALKOUT RIGHT ONTO THE BEACH (100 st ...

    From $575 per night (USD)

    VRBO

    Details
  • Luxury 2 bed condo Gulf front  - watch dolphins and sunsets from your sofa
    Click For Pricing

    VRBO

    Luxury 2 bed condo Gulf front - watch dolphins and sunsets from your sofa

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Sweeping panoramic full Gulf and Sarasota Bay/skyline views from wraparound terrace and every room in this beautifully ...

    Click For Pricing

    VRBO

    Details
  • Oceanfront townhouse w\/ shared pool and stunning panoramic water views
    Click For Pricing

    VRBO

    Oceanfront townhouse w\/ shared pool and stunning panoramic water views

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    6

    Longboat Pass Panorama Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...

    Click For Pricing

    VRBO

    Details
  • âš“Bay Haven! Waterfront condo steps away from the beach!⚓🌅
    From $165 per night (USD)

    Expedia

    ⚓Bay Haven! Waterfront condo steps away from the beach!⚓🌅

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Welcome to Bay Haven your WATERFRONT second-floor condo located in Longboat Key on Whitney Beach Bay Side. Whitney Beach ...

    From $165 per night (USD)

    Expedia

    Details
  • Fully Renovated Gulf Front Condo 2\/2
    From $275 per night (USD)

    VRBO

    Fully Renovated Gulf Front Condo 2\/2

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Experience sweeping beaches and direct Gulf of Mexico views from this beautifully updated coastal retreat on Longboat Ke ...

    From $275 per night (USD)

    VRBO

    Details
  • Longboat Key Condo w\/Lanai, Walk to Beach & Shops
    From $84 per night (USD)

    Expedia

    Longboat Key Condo w\/Lanai, Walk to Beach & Shops

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Enjoy the sun and sand when you stay at this vacation rental condo in Longboat Key! The 2-bedroom, 1-bathroom abode is l ...

    From $84 per night (USD)

    Expedia

    Details
  • Welcome To Paradise!
    From $275 per night (USD)

    VRBO

    Welcome To Paradise!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Enjoy staying at this one of kind beach bungalow for your special occasions or just a family fun retreat. Built-in 1930, ...

    From $275 per night (USD)

    VRBO

    Details
  • Luxury Waterfront on Longboat Key - 5 min walk to the beach
    From $655 per night (USD)

    VRBO

    Luxury Waterfront on Longboat Key - 5 min walk to the beach

    Bedrooms:
    6
    Bathrooms:
    4
    Sleeps:
    8

    Couple blocks from the beach and equipped with an elevator, this home offers upscale comforts including all new furnishi ...

    From $655 per night (USD)

    VRBO

    Details
  • Luxury home with lagoon-style pool!
    From $1646 per night (USD)

    VRBO

    Luxury home with lagoon-style pool!

    Bedrooms:
    10
    Bathrooms:
    9
    Sleeps:
    22

    Tide of Your Life by AMI Locals Home in Bradenton, FL Highlights: • 1 block from the beach • Lagoon-style pool with swi ...

    From $1646 per night (USD)

    VRBO

    Details
  • Beachcomber unit 403
    From $271 per night (USD)

    Expedia

    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 $271 per night (USD)

    Expedia

    Details
  • Beachcomber unit 503
    From $255 per night (USD)

    VRBO

    Beachcomber unit 503

    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 $255 per night (USD)

    VRBO

    Details
  • Beachcomber unit 405
    From $267 per night (USD)

    Expedia

    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 $267 per night (USD)

    Expedia

    Details
  • Beachcomber unit 203
    From $264 per night (USD)

    VRBO

    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 $264 per night (USD)

    VRBO

    Details
  • Beachcomber unit 608
    From $355 per night (USD)

    Expedia

    Beachcomber unit 608

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    2 bedroom; 2 bath (showers only) sixth floor condo overlooking the Gulf of Mexico Beach front units are ava ...

    From $355 per night (USD)

    Expedia

    Details
  • Beachcomber unit 303
    From $261 per night (USD)

    VRBO

    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 $261 per night (USD)

    VRBO

    Details
  • Beachcomber unit 204
    From $413 per night (USD)

    Expedia

    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 $413 per night (USD)

    Expedia

    Details
  • Beachcomber unit 208
    From $378 per night (USD)

    VRBO

    Beachcomber unit 208

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to The Beachcomber, a Longboat Key beach resort located right on the Gulf of Mexico. Just a few steps from your ...

    From $378 per night (USD)

    VRBO

    Details
  • Beachcomber unit 305
    From $246 per night (USD)

    Expedia

    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 $246 per night (USD)

    Expedia

    Details
  • Longboat Key Luxury Condo - walking to St. Armand's Circle!
    From $878 per night (USD)

    VRBO

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

    Bedrooms:
    2
    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 $878 per night (USD)

    VRBO

    Details
  • A home between the beach and lush park on the bay
    Click For Pricing

    VRBO

    A home between the beach and lush park on the bay

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    2

    Find peace and quiet at our quaint beach cottage on a quiet street in mid Longboat Key near the North End close to favor ...

    Click For Pricing

    VRBO

    Details
  • Canal Front Home - 5 min walk to beach.  RRR-00953.2023
    From $650 per night (USD)

    VRBO

    Canal Front Home - 5 min walk to beach. RRR-00953.2023

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Completely remodeled in 2022 this canal front home is located on the beautiful Island of Longboat Key. Park your boat i ...

    From $650 per night (USD)

    VRBO

    Details
  • BEACH CONDO LONG BOAT KEY - FULLY REMODELED!
    From $245 per night (USD)

    VRBO

    BEACH CONDO LONG BOAT KEY - FULLY REMODELED!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    2 Bedrooms, 2 bathroom, gulf side, private beach, white sand, kid friendly, elevator Welcome to our beach side condo, wh ...

    From $245 per night (USD)

    VRBO

    Details
  • 7th Heaven by Duncan Real Estate
    From $226 per night (USD)

    VRBO

    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 $226 per night (USD)

    VRBO

    Details
  • Veranda Beach front property and pool, school vacation week
    Click For Pricing

    Expedia

    Veranda Beach front property and pool, school vacation week

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Beautiful partial ocean view of Gulf of Mexico. Corner unit with two balconies. 2 bedrooms, each with their own bath. Sl ...

    Click For Pricing

    Expedia

    Details
  • 228 ONE-BEDROOM - Diplomat Beach Resort
    From $247 per night (USD)

    VRBO

    228 ONE-BEDROOM - Diplomat Beach Resort

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Luscious shades of dark green and coordinating floral comfy sleeper sofa and love seat make unwinding at the Gulf such a ...

    From $247 per night (USD)

    VRBO

    Details
  • 223 STUDIO - Diplomat Beach Resort
    From $236 per night (USD)

    Expedia

    223 STUDIO - Diplomat Beach Resort

    Bedrooms:
    1
    Bathrooms:
    0
    Sleeps:
    2

    Gulf facing unit nautically decorated with king size bed makes this studio a comfortable stay. Light wood furniture and ...

    From $236 per night (USD)

    Expedia

    Details
  • 243 ONE-BEDROOM - Diplomat Beach Resort
    From $271 per night (USD)

    VRBO

    243 ONE-BEDROOM - Diplomat Beach Resort

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    This spacious one-bedroom suite offers all the amenities of home with the excitement of a beachfront vacation on the Gul ...

    From $271 per night (USD)

    VRBO

    Details
  • 261 STUDIO - Diplomat Beach Resort
    From $228 per night (USD)

    Expedia

    261 STUDIO - Diplomat Beach Resort

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Enjoy watching the dolphins play and gorgeous sunsets are best observed from this second-floor studio. New king-size ma ...

    From $228 per night (USD)

    Expedia

    Details
  • 217 ONE-BEDROOM - Diplomat Beach Resort
    From $247 per night (USD)

    VRBO

    217 ONE-BEDROOM - Diplomat Beach Resort

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Comfy and cozy ground floor one bedroom condo with great lighting, footsteps away from pool and beach. Updated terrazzo ...

    From $247 per night (USD)

    VRBO

    Details
  • 225 STUDIO - Diplomat Beach Resort
    From $223 per night (USD)

    Expedia

    225 STUDIO - Diplomat Beach Resort

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Floral designs in soft pastels greet you as you enter this comfortably tiled studio. Gulf views and beach decor make yo ...

    From $223 per night (USD)

    Expedia

    Details
  • 255 STUDIO - Diplomat Beach Resort
    From $224 per night (USD)

    VRBO

    255 STUDIO - Diplomat Beach Resort

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Second floor gulf front studio with a modern style neutral tones. Comfortable and cozy with a king bed, swivel recliner, ...

    From $224 per night (USD)

    VRBO

    Details
  • 226 STUDIO - Diplomat Beach Resort
    From $224 per night (USD)

    Expedia

    226 STUDIO - Diplomat Beach Resort

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Totally remodeled studio with a Tommy Bahama flair. Completely tiled throughout with earth tones for that warm, homey fe ...

    From $224 per night (USD)

    Expedia

    Details
  • 265 ONE-BEDROOM - Diplomat Beach Resort
    From $265 per night (USD)

    VRBO

    265 ONE-BEDROOM - Diplomat Beach Resort

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Sit on the balcony and enjoy beautiful views of the Gulf of Mexico from this second floor contemporary one-bedroom condo ...

    From $265 per night (USD)

    VRBO

    Details
  • 256 ONE-BEDROOM - Diplomat Beach Resort
    From $265 per night (USD)

    Expedia

    256 ONE-BEDROOM - Diplomat Beach Resort

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Second floor one bedroom condo with light rattan and wicker makes this space most enjoyable. The comfy condo two full s ...

    From $265 per night (USD)

    Expedia

    Details
  • 212 ONE-BEDROOM - Diplomat Beach Resort
    From $268 per night (USD)

    VRBO

    212 ONE-BEDROOM - Diplomat Beach Resort

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Welcome to unit 212! Conveniently located on the first floor of the south building, this apartment offers not only magn ...

    From $268 per night (USD)

    VRBO

    Details
  • 239 ONE-BEDROOM - Diplomat Beach Resort
    From $265 per night (USD)

    Expedia

    239 ONE-BEDROOM - Diplomat Beach Resort

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Modern comfort & convenience meet hi-tech & sophistication to make this a home away from home that wants for nothing. So ...

    From $265 per night (USD)

    Expedia

    Details
  • 240 ONE-BEDROOM - Diplomat Beach Resort
    From $265 per night (USD)

    VRBO

    240 ONE-BEDROOM - Diplomat Beach Resort

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Fresh renovations enhance your stay in this wonderfully comfortable and spacious one bedroom unit. The bedroom has both ...

    From $265 per night (USD)

    VRBO

    Details
  • 224 STUDIO - Diplomat Beach Resort
    From $210 per night (USD)

    Expedia

    224 STUDIO - Diplomat Beach Resort

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Tastefully decorated in Modern Coastal decor, this downstairs studio unit has undergone a complete remodel and is straig ...

    From $210 per night (USD)

    Expedia

    Details
  • 216 ONE-BEDROOM - Diplomat Beach Resort
    From $265 per night (USD)

    VRBO

    216 ONE-BEDROOM - Diplomat Beach Resort

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    The living area of this unit that overlooks the beach level is in Floral shades of blue with blue carpeting that make th ...

    From $265 per night (USD)

    VRBO

    Details
  • 210 ONE-BEDROOM - Diplomat Beach Resort
    From $247 per night (USD)

    Expedia

    210 ONE-BEDROOM - Diplomat Beach Resort

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Spacious ground floor, end unit with lots of natural light. Good location , low traffic area, convenient tiki situated ...

    From $247 per night (USD)

    Expedia

    Details
  • 221 ONE-BEDROOM - Diplomat Beach Resort
    From $268 per night (USD)

    VRBO

    221 ONE-BEDROOM - Diplomat Beach Resort

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Welcome to paradise! Beautifully decorated with designer's touches. This 1 bedroom unit is completely updated and furni ...

    From $268 per night (USD)

    VRBO

    Details
  • 227 STUDIO - Diplomat Beach Resort
    From $227 per night (USD)

    Expedia

    227 STUDIO - Diplomat Beach Resort

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    You will be only steps from the beautiful 500' of beachfront and from the pool. This remodeled/redecorated 1st floor stu ...

    From $227 per night (USD)

    Expedia

    Details
  • 215 ONE BEDROOM - Diplomat Beach Resort
    From $268 per night (USD)

    VRBO

    215 ONE BEDROOM - Diplomat Beach Resort

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Comfy and cozy ground floor one bedroom condo with a king bed . Seashells, books and oversized soft furniture, with slee ...

    From $268 per night (USD)

    VRBO

    Details
  • 220 STUDIO - Diplomat Beach Resort
    From $226 per night (USD)

    Expedia

    220 STUDIO - Diplomat Beach Resort

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Nicely updated with tiled flooring, a modern kitchen and the totally updated bathroom features a walk-in shower. The un ...

    From $226 per night (USD)

    Expedia

    Details
  • 269 ONE-BEDROOM - Diplomat Beach Resort
    From $265 per night (USD)

    VRBO

    269 ONE-BEDROOM - Diplomat Beach Resort

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Light wicker furniture give this one bedroom end unit a spacious feel as soft seashell accents and wicker furniture make ...

    From $265 per night (USD)

    VRBO

    Details
  • 248 STUDIO - Diplomat Beach Resort
    From $226 per night (USD)

    Expedia

    248 STUDIO - Diplomat Beach Resort

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Welcome to Unit 248 where your stay is sure to be relaxing and comfortable ! This second floor studio has been remode ...

    From $226 per night (USD)

    Expedia

    Details
  • 229 STUDIO - Diplomat Beach Resort
    From $212 per night (USD)

    VRBO

    229 STUDIO - Diplomat Beach Resort

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Step out onto the beautiful gulf beach from this newly remodeled ground floor studio. The kitchen and bath have been co ...

    From $212 per night (USD)

    VRBO

    Details
  • 254 STUDIO - Diplomat Beach Resort
    From $228 per night (USD)

    Expedia

    254 STUDIO - Diplomat Beach Resort

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Brand new kitchen with granite counter tops and dishwasher. The same granite countertop and a new sink were also instal ...

    From $228 per night (USD)

    Expedia

    Details
  • 244 STUDIO - Diplomat Beach Resort
    From $229 per night (USD)

    VRBO

    244 STUDIO - Diplomat Beach Resort

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Amazing view of the Gulf from this upper floor unit. Decorated in hues of taupe, aqua and grey. New tile flooring throug ...

    From $229 per night (USD)

    VRBO

    Details
  • 245 ONE-BEDROOM - Diplomat Beach Resort
    From $265 per night (USD)

    Expedia

    245 ONE-BEDROOM - Diplomat Beach Resort

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Welcome to Florida in this beautifully and tropically decorated one bedroom unit. Terra Cotta tile throughout and two f ...

    From $265 per night (USD)

    Expedia

    Details
  • 236 ONE-BEDROOM - Diplomat Beach Resort
    From $265 per night (USD)

    VRBO

    236 ONE-BEDROOM - Diplomat Beach Resort

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Spacious fully tiled end unit with two full size beds and beige leather furnishings make your vacation even more enjoyab ...

    From $265 per night (USD)

    VRBO

    Details
  • 247-249 TWO-BEDROOM - Diplomat Beach Resort
    From $354 per night (USD)

    Expedia

    247-249 TWO-BEDROOM - Diplomat Beach Resort

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Sunny and bright this spacious and comfy two bedroom condo is a vacationers delight. Tile and carpet throughout add to ...

    From $354 per night (USD)

    Expedia

    Details
  • 246 STUDIO - Diplomat Beach Resort
    From $228 per night (USD)

    VRBO

    246 STUDIO - Diplomat Beach Resort

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Welcome to this direct beachfront condominium unit #246 with spectacular ocean, beach and sunset views. This condominium ...

    From $228 per night (USD)

    VRBO

    Details
  • 235 ONE-BEDROOM - Diplomat Beach Resort
    From $265 per night (USD)

    Expedia

    235 ONE-BEDROOM - Diplomat Beach Resort

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Very attractively decorated condo with rainbow colors on white wicker furniture make this not only relaxing but fun in t ...

    From $265 per night (USD)

    Expedia

    Details
  • Private Club Villa on Long Boat Key w\/ Olympic Sized Community Pool
    From $166 per night (USD)

    VRBO

    Private Club Villa on Long Boat Key w\/ Olympic Sized Community Pool

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    6

    Villa is 15 steps from your own private sugar sand bay beach. Cedars East Resort is a unique vacation getaway nestled w ...

    From $166 per night (USD)

    VRBO

    Details
  • Island Hideaway with Boat Parking! Steps to the Sand!
    From $115 per night (USD)

    VRBO

    Island Hideaway with Boat Parking! Steps to the Sand!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Discover this quaint one-bedroom guest house tucked away in a peaceful corner lot with front screened patio & landscaped ...

    From $115 per night (USD)

    VRBO

    Details
  • Gorgeous Beachfront ~ Spacious & Updated 2\/2 ~ Heated Saltwater Pool
    From $324 per night (USD)

    VRBO

    Gorgeous Beachfront ~ Spacious & Updated 2\/2 ~ Heated Saltwater Pool

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    This luxury beach getaway is waiting for you to enjoy. It is directly overlooking the beautiful shores and sparkling tu ...

    From $324 per night (USD)

    VRBO

    Details
  • Seasonal beach rental
    Click For Pricing

    VRBO

    Seasonal beach rental

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Available for 2020/2021 seasonal beach rental with beautiful Gulf of Mexico views from this spacious, corner apartment. ...

    Click For Pricing

    VRBO

    Details
  • 218 STUDIO - Diplomat Beach Resort
    From $205 per night (USD)

    VRBO

    218 STUDIO - Diplomat Beach Resort

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Beachfront ground floor studio unit with amazing gulf views. Remodeled with new furniture, kitchen cabinets/countertops ...

    From $205 per night (USD)

    VRBO

    Details
  • 250 STUDIO - Diplomat Beach Resort
    From $220 per night (USD)

    Expedia

    250 STUDIO - Diplomat Beach Resort

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Newly renovated in the Spring of 2022 This second floor efficiency is in a great location directly on the beach with a ...

    From $220 per night (USD)

    Expedia

    Details
  • 253 STUDIO - Diplomat Beach Resort
    From $224 per night (USD)

    VRBO

    253 STUDIO - Diplomat Beach Resort

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Beachfront studio unit with amazing ocean views. Completely remodeled with new furniture, cabinets, appliances, counter ...

    From $224 per night (USD)

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  • 230 ONE-BEDROOM - Diplomat Beach Resort
    From $247 per night (USD)

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    230 ONE-BEDROOM - Diplomat Beach Resort

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Escape to paradise! Brand new furnishings! After shelling, sightseeing or doing "nothing" at all, enjoy your home-away- ...

    From $247 per night (USD)

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  • 252 STUDIO - Diplomat Beach Resort
    From $225 per night (USD)

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    252 STUDIO - Diplomat Beach Resort

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    With its nautical colors, this studio is the ideal beachy getaway for your vacation on the Gulf. The comfortable furnit ...

    From $225 per night (USD)

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  • Beachcomber unit 202
    From $394 per night (USD)

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    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 $394 per night (USD)

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  • Beachcomber unit 501
    From $271 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 $271 per night (USD)

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  • PROMO 5% WEEKLY AND 10% MONTHLY DISCOUNT\nPrivate Beach Back Yard ! 5 BR 2 Bath
    From $299 per night (USD)

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    PROMO 5% WEEKLY AND 10% MONTHLY DISCOUNT\nPrivate Beach Back Yard ! 5 BR 2 Bath

    Bedrooms:
    2
    Bathrooms:
    5
    Sleeps:
    16

    Your tropical oasis awaits! Our spacious, newly decorated coastal chic 5 bdrm/2 bath home is just 2 miles from the beaut ...

    From $299 per night (USD)

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  • Metropolitan luxury in the sky by FVC
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    Metropolitan luxury in the sky by FVC

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    8th floor condo offered by Florida Vacation Connection. Large floor plan decorated with a taste and artistic elegance. ...

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  • Beachcomber unit 201
    From $251 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 $251 per night (USD)

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  • Island Sanctuary
    From $347 per night (USD)

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    Island Sanctuary

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    5

    Beautiful home in one of the most desirable areas of Longboat Key. Everything you need for your beach getaway. Walk to p ...

    From $347 per night (USD)

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  • Unit #114 Sand Cay Beach Resort Pool and Garden View
    From $307 per night (USD)

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    Unit #114 Sand Cay Beach Resort Pool and Garden 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 $307 per night (USD)

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  • Unit #203 Sand Cay Beach Resort Gulf Front
    From $431 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 $431 per night (USD)

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  • Unit #204 Sand Cay Beach Resort Gulf Front
    From $381 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 $381 per night (USD)

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  • Unit #111 Sand Cay Beach Resort Pool and Garden View
    From $302 per night (USD)

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    Unit #111 Sand Cay Beach Resort Pool and Garden 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 $302 per night (USD)

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  • Unit #106 Sand Cay Beach Resort Gulf View
    From $401 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 $401 per night (USD)

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  • Unit #201 Sand Cay Beach Resort Gulf View
    From $352 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 $352 per night (USD)

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  • Unit #209 Sand Cay Beach Resort Pool and Garden View
    From $278 per night (USD)

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    Unit #209 Sand Cay Beach Resort Pool and Garden 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 $278 per night (USD)

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  • Unit #303 Sand Cay Beach Resort Gulf Front
    From $431 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 $431 per night (USD)

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  • Unit #120 Sand Cay Beach Resort Gulf View
    From $347 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 $347 per night (USD)

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  • Unit #320 Sand Cay Beach Resort Gulf Front
    From $401 per night (USD)

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    Unit #320 Sand Cay Beach Resort Gulf Front

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

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

    From $401 per night (USD)

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  • Unit #105 Sand Cay Beach Resort Gulf View
    From $347 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 $347 per night (USD)

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  • Unit #205 Sand Cay Beach Resort  Gulf View
    From $341 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 $341 per night (USD)

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  • Unit #104 Sand Cay Beach Resort Gulf Front
    From $409 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 $409 per night (USD)

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    Details
  • Unit #107 Sand Cay Beach Resort Pool and Garden View
    From $319 per night (USD)

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    Unit #107 Sand Cay Beach Resort Pool and Garden 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 $319 per night (USD)

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  • Unit #116 Sand Cay Beach Resort Gulf Front
    From $387 per night (USD)

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    Unit #116 Sand Cay Beach Resort Gulf Front

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    First floor Gulf front. Queen bed in the master, Two full beds in guest bedroom. The views make you want to bask in the ...

    From $387 per night (USD)

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  • Unit #311 Sand Cay Beach Resort Pool and Garden View
    From $278 per night (USD)

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    Unit #311 Sand Cay Beach Resort Pool and Garden 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 $278 per night (USD)

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  • Unit #219 Sand Cay Beach Resort Gulf Front
    From $431 per night (USD)

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    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 $431 per night (USD)

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  • Unit #217 Sand Cay Beach Resort Gulf Front
    From $453 per night (USD)

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    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 $453 per night (USD)

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  • Unit #117 Sand Cay Beach Resort Gulf Front
    From $498 per night (USD)

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    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 $498 per night (USD)

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  • Unit #306 Sand Cay Beach Resort Gulf View
    From $347 per night (USD)

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    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 $347 per night (USD)

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  • Unit #315 Sand Cay Beach Resort Gulf View
    From $367 per night (USD)

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    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 $367 per night (USD)

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  • Unit #301 Sand Cay Beach Resort Gulf View 7 Night Minimum
    From $392 per night (USD)

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    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 $392 per night (USD)

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  • Unit #307 Sand Cay Beach Resort Pool and Garden
    From $307 per night (USD)

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    Unit #307 Sand Cay Beach Resort Pool and Garden

    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 $307 per night (USD)

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  • Unit #216 Sand Cay Beach Resort Gulf Front
    From $387 per night (USD)

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    Unit #216 Sand Cay Beach Resort Gulf Front

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Salt life could not be better! This unit is under new ownership and has been updated top to bottom, inside and out…all e ...

    From $387 per night (USD)

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  • Unit #215 Sand Cay Beach Resort Gulf View
    From $346 per night (USD)

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    Unit #215 Sand Cay Beach Resort Gulf View

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    2nd Floor Non-Smoking Gulf Front Unit. Unit COMPLETLY renovated and NEWLY furnished. Spectacular sunset views of the Gul ...

    From $346 per night (USD)

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  • Unit #118 Sand Cay Beach Resort Gulf Front
    From $349 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 $349 per night (USD)

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    Details
  • Unit #109 Sand Cay Beach Resort Pool and Garden View
    From $329 per night (USD)

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    Unit #109 Sand Cay Beach Resort Pool and Garden 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 $329 per night (USD)

    Expedia

    Details