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      Beachfront Vacation Rentals in Longboat Key

      Compare 16 beachfront vacation rentals and Airbnbs in Longboat Key with heated pools and free WiFi. Check ratings and prices before you book your stay

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      Rooms and Guests2 Guests, 1 room
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      Rooms and Guests2 Guests, 1 room
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      Check-in
      Wed, 11 Nov
      -
      Check-out
      Thu, 12 Nov
      Rooms and Guests2 Guests, 1 room
      1Filter & Sort
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      Hotels
      Vacation rentals
      All types
      Apartments (4)Villas (12)
      1-16 out of 16
      Sort by: high popularity
      • Price: low to high
      • Price: high to low
      • Guest rating: high to low
      • Popularity: high to low
      Sea Club IApartment
      8.8
      Great
      The largest option:
      4 adults
      2 bedrooms
      3 beds
      Map
      1.9 mi from City Center
      Private BeachHeated PoolWater Sports
      • Private beachfront with sea views
      • Heated pool with panoramic view
      • On-site water sports and tennis
      FromUS$ 288 /nightSelect
      The Beach On Longboat KeyApartment
      7.6
      Very good
      4 adults
      1 bedroom
      2 beds
      Map
      2.8 mi from City Center
      Private BeachHeated PoolChildren's Playground
      • Direct beach access from every unit
      • Individually styled no two alike
      • Children's playground on site
      FromUS$ 349 /nightSelect
      Little Gull Cottages By CoolvacayApartment
      9.5
      Perfect
      Map
      435 yd from City Center
      Private BeachHeated PoolGame Room
      • Private beach area
      • Fully equipped kitchen with fireplace
      • Outdoor play equipment for kids
      FromUS$ 382 /nightSelect
      Cabana Beach Club #5BHoliday home
      7.0
      Very good
      Map
      981 yd from City Center
      Beach AccessHeated PoolTennis Equipment
      • Direct beachfront access
      • Heated pool with views
      • On-site tennis equipment
      FromUS$ 240 /nightSelect
      Sutton Place #102AHoliday home
      Map
      1.6 mi from City Center
      Heated PoolFitness RoomPrivate Parking
      • 6-min walk to Longboat Key Beach
      • Heated pool with outdoor dining
      • Fully equipped kitchen & barbecue
      Select
      Beach Castle Resort #5Holiday home
      9.3
      Perfect
      Map
      516 yd from City Center
      Tennis CourtJacuzziSwimming Pool
      • Beachfront with sea-view balcony
      • On-site tennis court and jacuzzi
      • Horseback riding on property
      Select
      Beach Harbor Club F202Holiday home
      Map
      2.5 mi from City Center
      Heated PoolFitness RoomGarden
      • Heated pool with beach towels
      • Fitness room on-site
      • 3-minute walk to beach
      Select
      Cabana Beach Club #7Holiday home
      Map
      984 yd from City Center
      Heated PoolBeach AccessFitness Center
      • Direct beachfront holiday home
      • Heated pool with towels provided
      • Fully equipped kitchen in unit
      Select
      Portobello #204AHoliday home
      Map
      3.1 mi from City Center
      Heated PoolFitness CenterBeach Access
      • Direct beachfront with sea views
      • On-site children's playground
      • Fully equipped kitchen
      Select
      Outrigger Resort #6Holiday home
      Map
      823 yd from City Center
      Heated PoolFitness CenterFull Kitchen
      • Direct beachfront access with sea views
      • Heated outdoor pool
      • Fully equipped kitchen
      FromUS$ 366 /nightSelect
      Outrigger Resort #7Holiday home
      Map
      798 yd from City Center
      Heated PoolFitness CenterBeach Access
      • Direct beachfront access and sea views
      • Heated pool for year-round swimming
      • Fully equipped kitchen and balcony
      FromUS$ 386 /nightSelect
      Pelican Harbour, Beach Club T2Holiday home
      Map
      1.8 mi from City Center
      Heated PoolPlaygroundFitness Room
      • Heated swimming pool
      • Children's playground
      • Fully equipped kitchen
      Select
      Silver Sands #236Holiday home
      Map
      944 yd from City Center
      Heated PoolFitness CentreChildren's Playground
      • Direct beachfront access with garden views
      • Heated outdoor pool with pool towels
      • Children's playground and cycling nearby
      Select
      Outrigger Resort #4Holiday home
      Map
      809 yd from City Center
      BeachfrontHeated PoolFitness Room
      • Direct beachfront access
      • Heated outdoor pool
      • Two-bedroom home with kitchen
      FromUS$ 417 /nightSelect
      Whitney Beach 149Holiday home
      Map
      2.0 mi from City Center1128 yd from Beer Can Island
      WaterparkOutdoor PoolPrivate Entrance
      • On-site waterpark access
      • Private entrance for privacy
      • Outdoor pool with sun loungers
      Select
      Las Hermanas 2Apartment
      Map
      3.7 mi from City Center
      Beachfront AccessSpa CentrePrivate Parking
      • Direct beachfront with sea views
      • On-site spa and wellness centre
      • Full kitchen and private parking
      FromUS$ 448 /nightSelect

      Explore Hotels in Longboat Key by Feature

      Hotel themes
      Beachfront / Beach

      Longboat Key vacation rentals offer beachfront holiday homes with full kitchens, private pools, and direct beach access. Properties like Beach Harbor Club F202 and Cabana Beach Club #5B provide heated pools and free WiFi. Guests can expect spacious layouts, fitness rooms, and free parking. Most rentals are within a few minutes' walk of Longboat Key Beach.

      Budget varies; these holiday homes suit families and couples seeking privacy and amenities. Portobello #204A features a children's playground, while Beach Castle Resort #5 has a hot tub and superb guest rating. For beach lovers, Outrigger Resort #6 and Silver Sands #236 offer immediate sea views. Book early for summer stays to secure top choices.