Professionally Managed & Privately Owned Longboat Key Rentals

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135 Rentals Found

Longboat Key Beach house Rental 4 Bedrooms (#2777)

Stunning Views of Gulf Formal dining area overlooking the gulf
  • Vacation Home and Villa
  • 5 stars (Platinum)
  • 3 Bedrooms, Sleeps 6
  • 3 Bathrooms
  • Rates:
    $4795/week - $5695/week
  • Availability:
    Call 800-657-8966

Longboat Key Four Bedroom Vacation Rentals (#2218)

Luxury Estate Home on Longboat Key Walk to Longboat beach
  • Vacation Home and Villa
  • 5 stars (Platinum)
  • 4 Bedrooms, Sleeps 8
  • 4 Bathrooms
  • Rates:
    $18995/month - $24995/month
  • Availability:
    Call 800-657-8966

Longboat Key Club Vacation Home- Luxury (#6720)


  • Vacation Home and Villa
  • 5 stars (Platinum)
  • 3 Bedrooms, Sleeps 8
  • 3 Bathrooms
  • Rates:
    $11495/month - $18995/month
  • Availability:
    Call 800-657-8966

Longboat Key Rental with boat dock (#5334)

Living room Longboat Key vacation home
  • Vacation Home and Villa
  • 5 stars (Platinum)
  • 3 Bedrooms, Sleeps 10
  • 3 Bathrooms
  • Rates:
    $2695/week - $4895/week
  • Availability:
    Call 800-657-8966

5 bedroom Beach House on Longboat Key (#6071)

Living room Poolside lounging chairs
  • Vacation Home and Villa
  • 5 stars (Platinum)
  • 5 Bedrooms, Sleeps 10
  • 4 Bathrooms
  • Rates:
    $11,995/week - $13,495/week
  • Availability:
    Call 800-657-8966

Longboat Key Vacation Rental Home, 3 Bedrooms (#880457)

Beach front house for rent in Longboat Key, Florida Panoramic water view from living room
  • Vacation Home and Villa
  • 5 stars (Platinum)
  • 3 Bedrooms, Sleeps 6
  • 2 Bathrooms
  • Rates:
    $5300/month - $5300/month
  • Availability:
    Call 800-657-8966

Longboat Key Vacation Renta Home (#880453)

Bay view house for rent in Longboat Key, Florida Living room with fireplace
  • Vacation Home and Villa
  • 5 stars (Platinum)
  • 3 Bedrooms, Sleeps 8
  • 2 Bathrooms
  • Rates:
    $11400/month - $14000/month
  • Availability:
    Call 800-657-8966

High end Longboat Key Home for rent (#877154)

Longboat rental with private caged pool Luxury Longboat Key rental home
  • Vacation Home and Villa
  • 5 stars (Platinum)
  • 4 Bedrooms, Sleeps 8
  • 4 Bathrooms
  • Rates:
    $19,995/month - $26,995/month
  • Availability:
    Call 800-657-8966

Longboat Key Rental - Sleeps 8 - Bay Front (#879973)

Pool and Patio Area Walkway to the Bay
  • Vacation Home and Villa
  • 5 stars (Platinum)
  • 3 Bedrooms, Sleeps 8
  • 4 Bathrooms
  • Rates:
    $15000/month - $25000/month
  • Availability:
    Call 800-657-8966

Longboat Vacation Home- Luxury 3 Bedrooms Boat Dock (#878098)

Canal front vacation home in Longboat Key, Florida Open plan living space
  • Vacation Home and Villa
  • 5 stars (Platinum)
  • 3 Bedrooms, Sleeps 6
  • 4 Bathrooms
  • Rates:
    $6950/month - $13,200/month
  • Availability:
    Call 800-657-8966

Longboat Key Vacation Rental, 3 Bedrooms (#880455)

Gorgeus vacation home in Longoat Key. Florida Living room
  • Vacation Home and Villa
  • 5 stars (Platinum)
  • 3 Bedrooms, Sleeps 6
  • 3 Bathrooms
  • Rates:
    $2050/week - $2650/week
  • Availability:
    Call 800-657-8966

Longboat Key Vacation Rental Home, 3 Bedrooms (#880530)

Longboat Key, Florida vacation home with short walk to beach Designer furnished living room
  • Vacation Home and Villa
  • 5 stars (Platinum)
  • 3 Bedrooms, Sleeps 8
  • 3 Bathrooms
  • Rates:
    $3600/week - $4300/week
  • Availability:
    Call 800-657-8966

Longboat Key Rental - Boat Dock - One Block to Beach (#881744)

Canal front vacation home with comfortable furniture in Longboat Key, Florida Dining table & breakfast bar
  • Vacation Home and Villa
  • 5 stars (Platinum)
  • 3 Bedrooms, Sleeps 12+
  • 2 Bathrooms
  • Rates:
    $1350/week
  • Availability:
    Call 800-657-8966

Longboat Key Vacation Rental (#881121)

Canal front home for rent in Longboat Key, Florida Master bedroom with queen bed
  • Vacation Home and Villa
  • 5 stars (Platinum)
  • 3 Bedrooms, Sleeps 6
  • 3 Bathrooms
  • Rates:
    Call 800-657-8966
  • Availability:
    Call 800-657-8966

Longboat Key Vacation Rental Home (#881130)

Bay front home for rent in Longboat Key, Florida Open plan living space
  • Vacation Home and Villa
  • 5 stars (Platinum)
  • 4 Bedrooms, Sleeps 8
  • 4 Bathrooms
  • Rates:
    $14000/month - $14000/month
  • Availability:
    Call 800-657-8966

Longboat Key Vacation Rental Townhouse (#881132)

Canal front townhouse for rent ib Longboat Key, Florida Living room
  • Vacation Home and Villa
  • 5 stars (Platinum)
  • 2 Bedrooms, Sleeps 4
  • 2 Bathrooms
  • Rates:
    Call 800-657-8966
  • Availability:
    Call 800-657-8966

Longboat Key Vacation Rental (#881133)

Canal front townhouse in Longboat Key, Florida Living room
  • Vacation Home and Villa
  • 5 stars (Platinum)
  • 3 Bedrooms, Sleeps 6
  • 3 Bathrooms
  • Rates:
    Call 800-657-8966
  • Availability:
    Call 800-657-8966

Longboat Key Vacation Rental Home (#881146)

Canal front home for rent in Longboat Key, Florida Living room
  • Vacation Home and Villa
  • 5 stars (Platinum)
  • 3 Bedrooms, Sleeps 8
  • 2 Bathrooms
  • Rates:
    $5800/month - $6800/month
  • Availability:
    Call 800-657-8966

Longboat Key, Florida Home For Rent - Walk To Beach (#881659)

Luxurious vacation home in Longboat Key, Florida Spacious living room with Bay view
  • Vacation Home and Villa
  • 5 stars (Platinum)
  • 5 Bedrooms, Sleeps 11
  • 4 Bathrooms
  • Rates:
    $16000/month - $18000/month
  • Availability:
    Call 800-657-8966

Longboat Key Vacation Home- Walk to Beach (#881676)

Longboat Key, Florida rental home with short walk to beach Open living & dining area
  • Vacation Home and Villa
  • 5 stars (Platinum)
  • 2 Bedrooms, Sleeps 6
  • 1 Bathroom
  • Rates:
    $1325/week
  • Availability:
    Call 800-657-8966

Longboat Key Rental Home- Canal Front- Dock & Pool (#881679)

Canal front rental home in Longboat Key, Florida Living room
  • Vacation Home and Villa
  • 5 stars (Platinum)
  • 5 Bedrooms, Sleeps 12+
  • 4 Bathrooms
  • Rates:
    Call 800-657-8966
  • Availability:
    Call 800-657-8966

Bay Front Vacation Home in Longboat Key- Dock- Walk to Beach (#881681)

Bay front home for rent in Longboat Key, Florida Living room
  • Vacation Home and Villa
  • 5 stars (Platinum)
  • 5 Bedrooms, Sleeps 10
  • 5 Bathrooms
  • Rates:
    $4300/week
  • Availability:
    Call 800-657-8966

Longboat Key House for Rent- Only 200 Paces to Beach (#881685)

Longboat Key, Florida vacation home with short walk to beach Living room
  • Vacation Home and Villa
  • 5 stars (Platinum)
  • 4 Bedrooms, Sleeps 10
  • 3 Bathrooms
  • Rates:
    $3000/week
  • Availability:
    Call 800-657-8966

Pool, Dock & Hot Tub- Longboat Key Rental Home (#881704)

Canal front home for rent in Longboat Key, Florida Living room with flat screen TV
  • Vacation Home and Villa
  • 5 stars (Platinum)
  • 4 Bedrooms, Sleeps 10
  • 2 Bathrooms
  • Rates:
    $3300/week
  • Availability:
    Call 800-657-8966

Bay & Gulf View Rental Home in Longboat Key. (#881706)

Bay & gulf view vacation home in Longboat Key, Florida Gulf view from living room
  • Vacation Home and Villa
  • 5 stars (Platinum)
  • 4 Bedrooms, Sleeps 12+
  • 4 Bathrooms
  • Rates:
    $8900/week
  • Availability:
    Call 800-657-8966

Longboat Key Rental. Bay View. Dock & Pool (#881707)

Bay front home in Longboat Key, Florida Living room with flat screen TV
  • Vacation Home and Villa
  • 5 stars (Platinum)
  • 4 Bedrooms, Sleeps 8
  • 3 Bathrooms
  • Rates:
    Call 800-657-8966
  • Availability:
    Call 800-657-8966

Longboat Key Rental Home- Pool- Dock- Gulf & Canal View (#881711)

Gulf & canal view home for rent in Longboat Key, Florida Living room
  • Vacation Home and Villa
  • 5 stars (Platinum)
  • 4 Bedrooms, Sleeps 8
  • 3 Bathrooms
  • Rates:
    $4000/week
  • Availability:
    Call 800-657-8966

Large Luxurious Executive Pool Home in Longboat Key (#881713)

Deluxe vacation home with short walk to beach in Longboat Key, Florida Living room open to pool
  • Vacation Home and Villa
  • 5 stars (Platinum)
  • 4 Bedrooms, Sleeps 8
  • 3 Bathrooms
  • Rates:
    Call 800-657-8966
  • Availability:
    Call 800-657-8966

Vintage Charm Bungalow on Longboat Key- Walk to Beach (#881714)

Cottage for rent with short walk to beach in Longboat Key, Florida Living room
  • Vacation Home and Villa
  • 5 stars (Platinum)
  • 3 Bedrooms, Sleeps 6
  • 2 Bathrooms
  • Rates:
    Call 800-657-8966
  • Availability:
    Call 800-657-8966

Enjoy Pool, Beach and Sunsets in Longboat Key Rental Home (#881715)

Longboat Key, Florida rental home with pool Sitting/reading area
  • Vacation Home and Villa
  • 5 stars (Platinum)
  • 3 Bedrooms, Sleeps 12+
  • 2 Bathrooms
  • Rates:
    Call 800-657-8966
  • Availability:
    Call 800-657-8966

Luxury Home on Water - Canal - Dock - Boat Lift - Longboat Key (#881716)

Canal front home for rent in Longboat Key, Florida Open living & dining area
  • Vacation Home and Villa
  • 5 stars (Platinum)
  • 3 Bedrooms, Sleeps 6
  • 2 Bathrooms
  • Rates:
    $2000/week
  • Availability:
    Call 800-657-8966

Private Beach and Canal Home for Rent in Longboat Key (#881717)

Canal view home for rent in Longboat Key, Florida Main living space
  • Vacation Home and Villa
  • 5 stars (Platinum)
  • 3 Bedrooms, Sleeps 6
  • 3 Bathrooms
  • Rates:
    $2100/week
  • Availability:
    Call 800-657-8966

Beautiful House in Longboat Key- Movie Screening Room & Gym (#881718)

Longboat Key, Florida rental home with caged pool Living room  with fireplace
  • Vacation Home and Villa
  • 5 stars (Platinum)
  • 3 Bedrooms, Sleeps 8
  • 4 Bathrooms
  • Rates:
    $4700/week
  • Availability:
    Call 800-657-8966

Canal Front Longboat Key Rental- Pool & Hot Tub (#881720)

Canal front rental home with pool in Longboat Key, Florida Living room
  • Vacation Home and Villa
  • 5 stars (Platinum)
  • 3 Bedrooms, Sleeps 8
  • 2 Bathrooms
  • Rates:
    $11000/week
  • Availability:
    Call 800-657-8966

Longboat Key Rental- Pool & Dock- Canal Front (#881727)

Canal front vacation home in Longboat Key, Florida Open living & dning area
  • Vacation Home and Villa
  • 5 stars (Platinum)
  • 3 Bedrooms, Sleeps 8
  • 2 Bathrooms
  • Rates:
    $1800/week
  • Availability:
    Call 800-657-8966

Canal Front Home in Longboat Key. Pool, Boat Dock & Davit (#881734)

Canal front home in Longboat Key, Florida Living room
  • Vacation Home and Villa
  • 5 stars (Platinum)
  • 3 Bedrooms, Sleeps 6
  • 3 Bathrooms
  • Rates:
    $3000/week
  • Availability:
    Call 800-657-8966

Luxury Home with Private Beach in Longboat Key. (#881731)

Gulf front home for rent in Longboat Key, Florida Living room with fireplace
  • Vacation Home and Villa
  • 5 stars (Platinum)
  • 3 Bedrooms, Sleeps 6
  • 3 Bathrooms
  • Rates:
    $3000/week
  • Availability:
    Call 800-657-8966

Longboat Key Home For Rent- Private Heated Pool- Walk to Beach (#881735)

Longboat Key, Florida vacation home with heated pool Comfortable living room
  • Vacation Home and Villa
  • 5 stars (Platinum)
  • 3 Bedrooms, Sleeps 6
  • 3 Bathrooms
  • Rates:
    $1750/week
  • Availability:
    Call 800-657-8966

Longboat Key Bay Front Rental Home (#881749)

Bay view rental home in Longboat Key, Florida Extended living area
  • Vacation Home and Villa
  • 5 stars (Platinum)
  • 2 Bedrooms, Sleeps 4
  • 2 Bathrooms
  • Rates:
    $2200/week
  • Availability:
    Call 800-657-8966

La Jolla vacation rental (#882487)


  • Vacation Home and Villa
  • 5 stars (Platinum)
  • 5 Bedrooms, Sleeps 10
  • 5 Bathrooms
  • Rates:
    Call 800-657-8966
  • Availability:
    Call 800-657-8966

Montecito Vacation Villa, 6 minutes to Upper Village (#882498)


  • Vacation Home and Villa
  • 5 stars (Platinum)
  • 5 Bedrooms, Sleeps 10
  • 6 Bathrooms
  • Rates:
    Call 800-657-8966
  • Availability:
    Call 800-657-8966

Longboat Key Vacation Rental - Sleeps 6 - Short Walk to Beach (#5438)

Canal front home in Longboat Key, Florida Living room
  • Vacation Home and Villa
  • 4 stars (Gold)
  • 3 Bedrooms, Sleeps 6
  • 2 Bathrooms
  • Rates:
    $4495/month - $6995/month
  • Availability:
    Call 800-657-8966

Luxury Longboat Key vacation Home (#99034)

Longboat Key rental villa by the Bay Longboat rental with caged, lap pool
  • Vacation Home and Villa
  • 4 stars (Gold)
  • 3 Bedrooms, Sleeps 8
  • 4 Bathrooms
  • Rates:
    $3695/week - $4495/week
  • Availability:
    Call 800-657-8966

Longboat Key Vacation Home for Rent Three Bedrooms (#3222)

Luxury Longboat Key rental home Living room
  • Vacation Home and Villa
  • 4 stars (Gold)
  • 2 Bedrooms, Sleeps 6
  • 3 Bathrooms
  • Rates:
    $2495/week - $3995/week
  • Availability:
    Call 800-657-8966

Longboat Key Luxury Beach house Rental (#8971)


  • Vacation Home and Villa
  • 4 stars (Gold)
  • 3 Bedrooms, Sleeps 8
  • 4 Bathrooms
  • Rates:
    Call 800-657-8966
  • Availability:
    Call 800-657-8966

Longboat Key Beach house Rental (#6541)

Gulf view from private balcony Longboat Key house for rent
  • Vacation Home and Villa
  • 4 stars (Gold)
  • 2 Bedrooms, Sleeps 4
  • 2 Bathrooms
  • Rates:
    $2795/week - $4945/week
  • Availability:
    Call 800-657-8966

Longboat Key Vacation Home - Sleeps 12+ - Beachfront - Pool (#6889)

Longboat Key, Florida rental home with private pool View from bedroom
  • Vacation Home and Villa
  • 4 stars (Gold)
  • 6 Bedrooms, Sleeps 12+
  • 5 Bathrooms
  • Rates:
    $8495/week - $12000/week
  • Availability:
    Call 800-657-8966

Three Bedroom Vacation Rentals on Longboat Key (#6460)

Living room
  • Vacation Home and Villa
  • 4 stars (Gold)
  • 3 Bedrooms, Sleeps 6
  • 2 Bathrooms
  • Rates:
    $5000/month - $6995/month
  • Availability:
    Call 800-657-8966

Longboat Key Vacation Rental Home - Sleeps 8 - Private Beach (#6462)

Private pool & spa Exterior back
  • Vacation Home and Villa
  • 4 stars (Gold)
  • 4 Bedrooms, Sleeps 8
  • 2 Bathrooms
  • Rates:
    $3795/week - $3995/week
  • Availability:
    Call 800-657-8966

Longboat Key Vacation Beach Rental, 3 Bedrroms (#880456)

Longboat Key, Florida rental villa Living room
  • Vacation Home and Villa
  • 4 stars (Gold)
  • 3 Bedrooms, Sleeps 6
  • 2 Bathrooms
  • Rates:
    $3200/month - $3900/month
  • Availability:
    Call 800-657-8966

Vacation Homes Longboat (#6483)

Living room Longboat Key house for rent
  • Vacation Home and Villa
  • 4 stars (Gold)
  • 3 Bedrooms, Sleeps 6
  • 2 Bathrooms
  • Rates:
    $2495/week - $3195/week
  • Availability:
    Call 800-657-8966

Longboat Key Vacation Homes (#6487)

Poolside table set Living room
  • Vacation Home and Villa
  • 4 stars (Gold)
  • 2 Bedrooms, Sleeps 6
  • 3 Bathrooms
  • Rates:
    $1945/week - $2195/week
  • Availability:
    Call 800-657-8966

Vacation Home on Longboat Key (#6490)

Country Club Shores on Longboat Key guest bedroom with 2 beds
  • Vacation Home and Villa
  • 4 stars (Gold)
  • 3 Bedrooms, Sleeps 8
  • 2 Bathrooms
  • Rates:
    $1595/week - $2895/week
  • Availability:
    Call 800-657-8966

Longboat Key Vacation Rental Homes (#6511)

Longboat Key Beach Longboat Key house for rent
  • Vacation Home and Villa
  • 4 stars (Gold)
  • 3 Bedrooms, Sleeps 6
  • 2 Bathrooms
  • Rates:
    $2270/week - $3195/week
  • Availability:
    Call 800-657-8966

Longboat Key Rental Home - Sleeps 6 - Pool (#880277)

Canal front home for rent in Longboat Key, Florida Living room
  • Vacation Home and Villa
  • 4 stars (Gold)
  • 3 Bedrooms, Sleeps 6
  • 2 Bathrooms
  • Rates:
    $3195/week - $3995/week
  • Availability:
    Call 800-657-8966

Longboat Key Vacation Home (#880452)

Canal front home in Longboat Key,Florida Private pool
  • Vacation Home and Villa
  • 4 stars (Gold)
  • 3 Bedrooms, Sleeps 12+
  • 2 Bathrooms
  • Rates:
    $1695/week - $1999/week
  • Availability:
    Call 800-657-8966

Longboat Key Vacation Rental, Duplex (#880928)

Beach view vacation cottage in Longboat Key, Florida Living area open to porch
  • Vacation Home and Villa
  • 4 stars (Gold)
  • 2 Bedrooms, Sleeps 6
  • 2 Bathrooms
  • Rates:
    $2400/week
  • Availability:
    Call 800-657-8966

Longboat Key Home Rental With Water Views - Walk To Beach (#6736)


  • Vacation Home and Villa
  • 4 stars (Gold)
  • 3 Bedrooms, Sleeps 11
  • 3 Bathrooms
  • Rates:
    $5495/month - $7495/month
  • Availability:
    Call 800-657-8966

4 bedroom 3 Bath Vacation Rentals Longboat Key (#6737)

Canal front home in Longboat Key, Florida Porch has table set with umbrella
  • Vacation Home and Villa
  • 4 stars (Gold)
  • 4 Bedrooms, Sleeps 8
  • 3 Bathrooms
  • Rates:
    $5495/month - $9500/month
  • Availability:
    Call 800-657-8966

Longboat Key Vacation Home- Country Club Shores (#6738)

Private caged pool Living room
  • Vacation Home and Villa
  • 4 stars (Gold)
  • 4 Bedrooms, Sleeps 7
  • 3 Bathrooms
  • Rates:
    $2995/week - $4795/week
  • Availability:
    Call 800-657-8966

Longboat Key Beach Vacation Home with Pool (#6714)

Beach front home for rent in Longboat Key, Florida Living room
  • Vacation Home and Villa
  • 4 stars (Gold)
  • 4 Bedrooms, Sleeps 8
  • 3 Bathrooms
  • Rates:
    $5995/week - $7995/week
  • Availability:
    Call 800-657-8966

Longboat Key Vacation Rentals (#6007)

Living room Longboat Key house for rent
  • Vacation Home and Villa
  • 4 stars (Gold)
  • 3 Bedrooms, Sleeps 6
  • 2 Bathrooms
  • Rates:
    $4995/month - $8495/month
  • Availability:
    Call 800-657-8966

Longboat Key Villa for Rent (#6008)

Full-size kitchen Master bedroom with TV
  • Vacation Home and Villa
  • 4 stars (Gold)
  • 2 Bedrooms, Sleeps 6
  • 2 Bathrooms
  • Rates:
    $2495/week - $3695/week
  • Availability:
    Call 800-657-8966

Walk to Beach Longboat Key Rentals (#6027)

Living room Lovely Longboat Key rental home
  • Vacation Home and Villa
  • 4 stars (Gold)
  • 2 Bedrooms, Sleeps 6
  • 2 Bathrooms
  • Rates:
    $1395/week - $2995/week
  • Availability:
    Call 800-657-8966

Longboat Key Vacation Homes (#6959)

Charming Longboat Key, Florida rental home Living room
  • Vacation Home and Villa
  • 4 stars (Gold)
  • 2 Bedrooms, Sleeps 6
  • 2 Bathrooms
  • Rates:
    $2995/month - $5475/month
  • Availability:
    Call 800-657-8966

Three Bedroom Vacation Homes for Rent on Longboat Key (#6993)

Canal front home in Longboat Key, Florida Living room
  • Vacation Home and Villa
  • 4 stars (Gold)
  • 3 Bedrooms, Sleeps 6
  • 2 Bathrooms
  • Rates:
    $1995/week - $3495/week
  • Availability:
    Call 800-657-8966

Longboat Key Vacation Homes Three Bedrooms Sleeps Six (#6994)

Canal front home for rent in Longboat Key, Florida Boat dock
  • Vacation Home and Villa
  • 4 stars (Gold)
  • 3 Bedrooms, Sleeps 6
  • 2 Bathrooms
  • Rates:
    $4995/month - $6995/month
  • Availability:
    Call 800-657-8966

Beachfront Vacation Home Longboat Key (#6999)

Gulf front home for rent with pool in Longboat Key, Florida Living room
  • Vacation Home and Villa
  • 4 stars (Gold)
  • 3 Bedrooms, Sleeps 6
  • 3 Bathrooms
  • Rates:
    $4395/week - $6195/week
  • Availability:
    Call 800-657-8966

Longboat Key Beach House Rental 4 Bedrooms (#7000)

Beach front vacation home with pool in Longboat Key, Florida Open plan living space
  • Vacation Home and Villa
  • 4 stars (Gold)
  • 4 Bedrooms, Sleeps 8
  • 4 Bathrooms
  • Rates:
    $4995/week - $6995/week
  • Availability:
    Call 800-657-8966

Longboat Key Beach Front Vacation Home (#7001)

Beautiful beachfront home in Longboat Key, Florida Beach at Longboat Key, Florida
  • Vacation Home and Villa
  • 4 stars (Gold)
  • 5 Bedrooms, Sleeps 10
  • 4 Bathrooms
  • Rates:
    $5795/week - $7595/week
  • Availability:
    Call 800-657-8966

Three Bed Rental Longboat Key Florida (#6029)

Canal front home in Longboat Key, Florida Living room
  • Vacation Home and Villa
  • 4 stars (Gold)
  • 3 Bedrooms, Sleeps 6
  • 2 Bathrooms
  • Rates:
    $2235/week - $9495/month
  • Availability:
    Call 800-657-8966

Luxury Vacation Homes on Longboat -Home Sleeps 8 (#7008)

Canal front home for rent in Longboat Key, Florida Living room
  • Vacation Home and Villa
  • 4 stars (Gold)
  • 3 Bedrooms, Sleeps 8
  • 2 Bathrooms
  • Rates:
    $3795/month - $6995/month
  • Availability:
    Call 800-657-8966

Longboat Key Vacation - Beach Rental - Sleeps 10 (#7354)

walk to beach no roads to cross longboat key
  • Vacation Home and Villa
  • 4 stars (Gold)
  • 3 Bedrooms, Sleeps 10
  • 2 Bathrooms
  • Rates:
    $2395/week - $3495/week
  • Availability:
    Call 800-657-8966

Longboat Key Rental Home- On Beach (#5332)

Beach front rental home in Longboat Key, Florida Living room
  • Vacation Home and Villa
  • 4 stars (Gold)
  • 3 Bedrooms, Sleeps 8
  • 2 Bathrooms
  • Rates:
    $3500/week
  • Availability:
    Call 800-657-8966

Longboat Key three Bedroom Villa - 400 steps to the beach! (#876474)

Longboat Key, Florida vacation home with private pool Living room
  • Vacation Home and Villa
  • 4 stars (Gold)
  • 3 Bedrooms, Sleeps 6
  • 3 Bathrooms
  • Rates:
    $3995/month - $6495/month
  • Availability:
    Call 800-657-8966

Longboat Key Rental Home- Private Pool- Sleeps 8 (#876557)

Canal front home for rent in Longboat Key, Florida Living room
  • Vacation Home and Villa
  • 4 stars (Gold)
  • 3 Bedrooms, Sleeps 8
  • 2 Bathrooms
  • Rates:
    $2000/week
  • Availability:
    Call 800-657-8966

Longboat Key vacation Pool home (#876567)

Gorgeous Longboat Key rental Longboat Key rental is canal front
  • Vacation Home and Villa
  • 4 stars (Gold)
  • 3 Bedrooms, Sleeps 6
  • 2 Bathrooms
  • Rates:
    $4795/month - $6495/month
  • Availability:
    Call 800-657-8966

Longboat Key Vacation Home - Sleeps 7 - Short Walk to the Beach (#877242)

Canal front vacation home in Longboat Key Living room
  • Vacation Home and Villa
  • 4 stars (Gold)
  • 3 Bedrooms, Sleeps 7
  • 2 Bathrooms
  • Rates:
    $1295/week - $1995/week
  • Availability:
    Call 800-657-8966

Four Bedroom Longboat Key Rental Home (#877686)

walk to  north longboat key beach Front view of home with garage
  • Vacation Home and Villa
  • 4 stars (Gold)
  • 4 Bedrooms, Sleeps 8
  • 3 Bathrooms
  • Rates:
    $1695/week - $3295/week
  • Availability:
    Call 800-657-8966

Longboat Key Home Rental with Three Bedrooms (#877757)

Longboat Key Vacation rentals A charming Longboat Key rental
  • Vacation Home and Villa
  • 4 stars (Gold)
  • 3 Bedrooms, Sleeps 8
  • 2 Bathrooms
  • Rates:
    $1,595/week - $2,155/week
  • Availability:
    Call 800-657-8966

Longboat Key monthly Rental with Boat Dock (#877875)


  • Vacation Home and Villa
  • 4 stars (Gold)
  • 3 Bedrooms, Sleeps 6
  • 2 Bathrooms
  • Rates:
    $5795/month - $8995/month
  • Availability:
    Call 800-657-8966

Longboat Key Vacation Rental Home, 4 Bedrooms (#878065)

Deluxe rental home in Longboat Key, Florida Formal living room
  • Vacation Home and Villa
  • 4 stars (Gold)
  • 4 Bedrooms, Sleeps 10
  • 4 Bathrooms
  • Rates:
    $6495/month - $11395/month
  • Availability:
    Call 800-657-8966

Longboat Key House Rental with Pool (#878076)

Canal front home in Longboat Key, Florida Living room
  • Vacation Home and Villa
  • 4 stars (Gold)
  • 3 Bedrooms, Sleeps 8
  • 3 Bathrooms
  • Rates:
    $4250/month - $6995/month
  • Availability:
    Call 800-657-8966

3 Bedroom home with pool and dock on North-end of Longboat Key (#878137)

Longboat Key Vacation Rental
  • Vacation Home and Villa
  • 4 stars (Gold)
  • 3 Bedrooms, Sleeps 6
  • 2 Bathrooms
  • Rates:
    $5495/month - $7495/month
  • Availability:
    Call 800-657-8966

Country Club Shores Longboat Key Vacation (#878171)

Canal front rental home in Longboat Key, Florida Spacious living area
  • Vacation Home and Villa
  • 4 stars (Gold)
  • 3 Bedrooms, Sleeps 6
  • 3 Bathrooms
  • Rates:
    $1995/week - $2695/week
  • Availability:
    Call 800-657-8966

Luxury Longboat Key Vacation Home with Pool - Sleeps 8 (#879971)

Boat Dock
  • Vacation Home and Villa
  • 4 stars (Gold)
  • 3 Bedrooms, Sleeps 8
  • 2 Bathrooms
  • Rates:
    $3995/week - $4495/week
  • Availability:
    Call 800-657-8966

Longboat Key Vacation Rental Home, 4 Bedrooms (#880496)


  • Vacation Home and Villa
  • 4 stars (Gold)
  • 4 Bedrooms, Sleeps 10
  • 4 Bathrooms
  • Rates:
    $6500/month - $11395/month
  • Availability:
    Call 800-657-8966

Longboat Key Vacation Rental, Duplex (#880929)

Beach access Living room
  • Vacation Home and Villa
  • 4 stars (Gold)
  • 3 Bedrooms, Sleeps 6
  • 3 Bathrooms
  • Rates:
    $2200/week
  • Availability:
    Call 800-657-8966

Longboat Key Vacation Rental, Beach Duplex, 5 Bedrooms (#880932)

Fabulous duplex in Longboat Key, Florida Duplex 1 3bdr/3bath
  • Vacation Home and Villa
  • 4 stars (Gold)
  • 5 Bedrooms, Sleeps 10
  • 5 Bathrooms
  • Rates:
    $5100/week - $6700/night
  • Availability:
    Call 800-657-8966

Longboat Key Beautiful Bayside Home with Pool, Spa & Dock (#881708)

Bayside rental home in Longboat Key, Florida Living room
  • Vacation Home and Villa
  • 4 stars (Gold)
  • 4 Bedrooms, Sleeps 8
  • 4 Bathrooms
  • Rates:
    Call 800-657-8966
  • Availability:
    Call 800-657-8966

Longboat Key Vacation Home- Canal Front- Private Pool & Boat Dock (#881739)

Canal front home in Longboat Key, Florida Living room
  • Vacation Home and Villa
  • 4 stars (Gold)
  • 3 Bedrooms, Sleeps 8
  • 3 Bathrooms
  • Rates:
    $2430/week
  • Availability:
    Call 800-657-8966

Gulf View Vacation Home in Longboat Key (#881742)

Gulf view rental home in Longboat Key, Florida Open living & dining area
  • Vacation Home and Villa
  • 4 stars (Gold)
  • 3 Bedrooms, Sleeps 11
  • 2 Bathrooms
  • Rates:
    $2150/week
  • Availability:
    Call 800-657-8966

Beach Front Rental Condo in Longboat Key - Sleeps 8 (#881745)

Beach front rental condo in Longboat Key, Florida Open living & dining area
  • Vacation Home and Villa
  • 4 stars (Gold)
  • 2 Bedrooms, Sleeps 8
  • 2 Bathrooms
  • Rates:
    $3115/week
  • Availability:
    Call 800-657-8966

Longboat Key Vacation Home- Private Pool & Spa - Boat Dock (#881748)

Bay view home for rent in Longboat Key, Florida Living room
  • Vacation Home and Villa
  • 4 stars (Gold)
  • 2 Bedrooms, Sleeps 6
  • 2 Bathrooms
  • Rates:
    $2500/week
  • Availability:
    Call 800-657-8966

Charming Cottage for Rent in Longboat Key- Walk to Beach (#881771)

Charming cottage for rent in Longboat Key, Florida Living room
  • Vacation Home and Villa
  • 4 stars (Gold)
  • 2 Bedrooms, Sleeps 8
  • 2 Bathrooms
  • Rates:
    $1950/week
  • Availability:
    Call 800-657-8966

Canal Front Home in Longboat Key - Walk to Beach (#882167)

Canal front home with pool in Longboat Key, Florida Living room open to porch
  • Vacation Home and Villa
  • 4 stars (Gold)
  • 2 Bedrooms, Sleeps 4
  • 2 Bathrooms
  • Rates:
    $2495/week - $2995/week
  • Availability:
    Call 800-657-8966

Bay Front Rental Home in Longboat Key - Boat Dock -Pool & Hot Tub (#882171)

Bay front vacation home in Longboat Key, Florida Living room
  • Vacation Home and Villa
  • 4 stars (Gold)
  • 5 Bedrooms, Sleeps 10
  • 5 Bathrooms
  • Rates:
    $3495/week - $5494/week
  • Availability:
    Call 800-657-8966

Vacation Rentals On Longboat Key with 3 Bedrooms (#6521)

Spacious living room Longboat Key house for rent
  • Vacation Home and Villa
  • 3 stars (Silver)
  • 3 Bedrooms, Sleeps 6
  • 2 Bathrooms
  • Rates:
    $1655/week - $3195/week
  • Availability:
    Call 800-657-8966

Longboat Key Vacation Home Rental (#6580)

Downstairs living room Private pool
  • Vacation Home and Villa
  • 3 stars (Silver)
  • 3 Bedrooms, Sleeps 6
  • 3 Bathrooms
  • Rates:
    $1545/week - $1995/week
  • Availability:
    Call 800-657-8966

Longboat Key Vacation Rental - Sleeps 6 - Private Pool (#880349)

Poolside sun loungers & table set with umbrella Living Area with TV
  • Vacation Home and Villa
  • 3 stars (Silver)
  • 3 Bedrooms, Sleeps 6
  • 2 Bathrooms
  • Rates:
    $5795/month - $7995/month
  • Availability:
    Call 800-657-8966

Longboat rental beach cottage - 5 minute walk to the beach (#879176)

Longboat Key, Florida vacation cottage with short walk to beach Living room
  • Vacation Home and Villa
  • 3 stars (Silver)
  • 3 Bedrooms, Sleeps 7
  • 2 Bathrooms
  • Rates:
    $1195/week - $1995/week
  • Availability:
    Call 800-657-8966

Longboat Key Vacation Rental - 4 Bedroom Bay House - Sleeps 8 Guests with Private Pool and Hot Tub (#879022)

Longboat Key, Florida vacation condo with shared pool Living & dining area
  • Vacation Home and Villa
  • 3 stars (Silver)
  • 4 Bedrooms, Sleeps 10
  • 3 Bathrooms
  • Rates:
    $2800/week - $5055/week
  • Availability:
    Call 800-657-8966

Longboat Key Vacation Rental - 2 Bedroom - Sleeps 6 Guests (#879023)


  • Vacation Home and Villa
  • 3 stars (Silver)
  • 2 Bedrooms, Sleeps 6
  • 2 Bathrooms
  • Rates:
    $1470/week - $2070/week
  • Availability:
    Call 800-657-8966

Longboat Key Rental - One Bedroom Townhouse - Sleeps 4 Guests (#879017)

Living Area
  • Vacation Home and Villa
  • 3 stars (Silver)
  • 1 Bedroom, Sleeps 4
  • 1 Bathroom
  • Rates:
    $1470/night - $2295/night
  • Availability:
    Call 800-657-8966

Three Bedroom Vacation Home on Longboat Key (#6668)

This Longboat rental is a short walk to the beach Longboat rental with canal view and private pool
  • Vacation Home and Villa
  • 3 stars (Silver)
  • 3 Bedrooms, Sleeps 6
  • 2 Bathrooms
  • Rates:
    $1550/week - $1700/week
  • Availability:
    Call 800-657-8966

Vacation Rental Located on the North End of Longboat Key (#879281)

Canal front home for rent in Longboat Key, Florida Living room
  • Vacation Home and Villa
  • 3 stars (Silver)
  • 3 Bedrooms, Sleeps 6
  • 2 Bathrooms
  • Rates:
    $2000/week
  • Availability:
    Call 800-657-8966

Longboat Beach front property. (#880944)

View of Gulf
  • Vacation Home and Villa
  • 3 stars (Silver)
  • 2 Bedrooms, Sleeps 4
  • 2 Bathrooms
  • Rates:
    $1800/week - $2000/week
  • Availability:
    Call 800-657-8966

Longboat Homes for rent (#6002)

Living room Longboat Key house for rent
  • Vacation Home and Villa
  • 3 stars (Silver)
  • 3 Bedrooms, Sleeps 6
  • 2 Bathrooms
  • Rates:
    $3395/month - $5495/month
  • Availability:
    Call 800-657-8966

Longboat Key Vacation Home for Rent (#6203)


  • Vacation Home and Villa
  • 3 stars (Silver)
  • 2 Bedrooms, Sleeps 6
  • 2 Bathrooms
  • Rates:
    $1800/week - $2100/week
  • Availability:
    Call 800-657-8966

Longboat Key Vacation Rental - Short Walk to Beach - Private Pool (#6006)

Canal view rental home in Longboat Key, Florida Living room
  • Vacation Home and Villa
  • 3 stars (Silver)
  • 3 Bedrooms, Sleeps 6
  • 2 Bathrooms
  • Rates:
    $4795/month - $8495/month
  • Availability:
    Call 800-657-8966

Longboat Key Beach Home for Rent (#6919)

Longboat Key, Florida rental home on the beach Living room
  • Vacation Home and Villa
  • 3 stars (Silver)
  • 3 Bedrooms, Sleeps 6
  • 2 Bathrooms
  • Rates:
    $2495/week - $2995/week
  • Availability:
    Call 800-657-8966

Longboat Key Vacation Home - Sleeps 6 - Short Walk to Beach (#6953)

Longboat Key vacation rental home Living room
  • Vacation Home and Villa
  • 3 stars (Silver)
  • 3 Bedrooms, Sleeps 6
  • 2 Bathrooms
  • Rates:
    $1795/week - $3195/week
  • Availability:
    Call 800-657-8966

Longboat Key Beach Front Vacation Home- Four Bedrooms (#6997)

Gulf front vacation home in Longboat Key, Florida Living room with fireplace & falt screen TV
  • Vacation Home and Villa
  • 3 stars (Silver)
  • 4 Bedrooms, Sleeps 8
  • 4 Bathrooms
  • Rates:
    $2695/week - $3795/week
  • Availability:
    Call 800-657-8966

Longboat Key Vacation Home - Sleeps 4 - Canal View & Boat Dock (#7328)

Canal front home in Longboat Key Living room
  • Vacation Home and Villa
  • 3 stars (Silver)
  • 2 Bedrooms, Sleeps 4
  • 2 Bathrooms
  • Rates:
    $2495/week - $3995/week
  • Availability:
    Call 800-657-8966

Longboat Key Vacation Home - Sleeps 6 - Short Walk to Beach (#7361)

Short walk to beach Longboat Key vacation home Living room
  • Vacation Home and Villa
  • 3 stars (Silver)
  • 2 Bedrooms, Sleeps 6
  • 2 Bathrooms
  • Rates:
    $3495/month - $5495/month
  • Availability:
    Call 800-657-8966

Longboat Key Town House for Rent- Beach to Bay (#879013)

Chaise lounges bayside Longboat Key beach
  • Vacation Home and Villa
  • 3 stars (Silver)
  • 1 Bedroom, Sleeps 4
  • 1 Bathroom
  • Rates:
    $1200/week - $1500/week
  • Availability:
    Call 800-657-8966

A Quiet and Relaxing Longboat Key Vacation Villa (#880431)

Water View Entrance to Longboat Key Rental
  • Vacation Home and Villa
  • 3 stars (Silver)
  • 3 Bedrooms, Sleeps 6
  • 2 Bathrooms
  • Rates:
    $5995/month - $6995/month
  • Availability:
    Call 800-657-8966

5 bedroom Vacation Rental Longboat Key (#6048)

Living room with TV Longboat Key house for rent
  • Vacation Home and Villa
  • 3 stars (Silver)
  • 3 Bedrooms, Sleeps 6
  • 2 Bathrooms
  • Rates:
    $2260/week - $3210/week
  • Availability:
    Call 800-657-8966

Longboat Key 2 bedroom Cottage (#877218)

Pool Club Membership
  • Vacation Home and Villa
  • 3 stars (Silver)
  • 2 Bedrooms, Sleeps 6
  • 2 Bathrooms
  • Rates:
    $1795/week - $3195/week
  • Availability:
    Call 800-657-8966

Longboat Country Club Shores to the beach access (#877606)

Longboat Key, Florida vacation home with private pool Living room
  • Vacation Home and Villa
  • 3 stars (Silver)
  • 3 Bedrooms, Sleeps 6
  • 2 Bathrooms
  • Rates:
    $1795/week - $3495/week
  • Availability:
    Call 800-657-8966

Longboat Key Vacation Rental - Sleeps 6 - Located on Beach Fabulous Views (#877638)


  • Vacation Home and Villa
  • 3 stars (Silver)
  • 3 Bedrooms, Sleeps 6
  • 2 Bathrooms
  • Rates:
    $2895/week - $3295/week
  • Availability:
    Call 800-657-8966

Longboat Key (#877758)

Charming Longboat Key rental walk to beach from your Longboat Key Rental
  • Vacation Home and Villa
  • 3 stars (Silver)
  • 2 Bedrooms, Sleeps 6
  • 2 Bathrooms
  • Rates:
    $1395/week - $1880/week
  • Availability:
    Call 800-657-8966

3 Bedroom Canal Front Home with Pool and Dock (#878085)

Longboat Key Vacation Rental Longboat  Key Vacation Rental
  • Vacation Home and Villa
  • 3 stars (Silver)
  • 3 Bedrooms, Sleeps 6
  • 2 Bathrooms
  • Rates:
    Call 800-657-8966
  • Availability:
    Call 800-657-8966

Longboat Key rental Beach cottage (#878750)

Longboat rental sleeps 8 Charming Longboat rental cottage
  • Vacation Home and Villa
  • 3 stars (Silver)
  • 2 Bedrooms, Sleeps 8
  • 1 Bathroom
  • Rates:
    $1895/week - $2595/week
  • Availability:
    Call 800-657-8966

Longboat Key rental Holiday cottage (#878751)

Longboat rental sleeps 7 Longboat rental close to beach
  • Vacation Home and Villa
  • 3 stars (Silver)
  • 2 Bedrooms, Sleeps 7
  • 1 Bathroom
  • Rates:
    $1895/week - $2595/week
  • Availability:
    Call 800-657-8966

Longboat Key rental cottage -Sleeps 6 (#878752)

Longboat rental steps to the beach Longboat vacation rental sleeps 6
  • Vacation Home and Villa
  • 3 stars (Silver)
  • 2 Bedrooms, Sleeps 6
  • 1 Bathroom
  • Rates:
    $1895/week - $2595/week
  • Availability:
    Call 800-657-8966

Longboat Key rental - Gulf view - Sleeps 6 (#878753)

Longboat rental with Gulf view Charming Longboat rental cottage
  • Vacation Home and Villa
  • 3 stars (Silver)
  • 1 Bedroom, Sleeps 6
  • 1 Bathroom
  • Rates:
    $1795/week - $2495/week
  • Availability:
    Call 800-657-8966

Canal View Vacation Home with Pool in Longboat Key, Florida (#881524)

Canal view home with pool in Longboat Key, Florida Canal view
  • Vacation Home and Villa
  • 3 stars (Silver)
  • 3 Bedrooms, Sleeps 6
  • 2 Bathrooms
  • Rates:
    $4195/month - $6995/month
  • Availability:
    Call 800-657-8966

Spaciuos Single Level House in Longboat Key (#881741)

Longboat Key, Florida rental home with short walk to beach Living & dining area
  • Vacation Home and Villa
  • 3 stars (Silver)
  • 3 Bedrooms, Sleeps 10
  • 2 Bathrooms
  • Rates:
    $1450/week
  • Availability:
    Call 800-657-8966

Longboat Key Rental with Beach Across the Street (#881757)

Longboat Key, Florida vacation home with short walk to beach Living room
  • Vacation Home and Villa
  • 3 stars (Silver)
  • 2 Bedrooms, Sleeps 4
  • 3 Bathrooms
  • Rates:
    $2100/week
  • Availability:
    Call 800-657-8966

Longboat Key Rental Home- 2 Bedroom- Sleeps 6 (#881759)

Longboat Key rental home with short walk to beach Living room
  • Vacation Home and Villa
  • 3 stars (Silver)
  • 2 Bedrooms, Sleeps 6
  • 1 Bathroom
  • Rates:
    $1325/week
  • Availability:
    Call 800-657-8966

Longboat Key Rental Home - Private Pool & Hot Tub (#881899)

Longboat Key, Florida rental home with pool & hot tub Exterior view of property
  • Vacation Home and Villa
  • 3 stars (Silver)
  • 3 Bedrooms, Sleeps 6
  • 2 Bathrooms
  • Rates:
    $4695/week - $5695/week
  • Availability:
    Call 800-657-8966

Longboat Key Vacation - Sleeps 6 - On Beach - Gulf View (#6481)

Private deck with outdoor furniture
  • Vacation Home and Villa
  • 2 stars (Bronze)
  • 3 Bedrooms, Sleeps 6
  • 2 Bathrooms
  • Rates:
    $1695/week - $2595/week
  • Availability:
    Call 800-657-8966

Longboat Key Vacation Rental - Seeps 6 - Short Walk to Beach (#7334)


  • Vacation Home and Villa
  • 2 stars (Bronze)
  • 3 Bedrooms, Sleeps 6
  • 2 Bathrooms
  • Rates:
    $3595/month - $4995/month
  • Availability:
    Call 800-657-8966

Longboat Rental Home Close to Beach-Pet Friendly Rentals (#3623)

Living room Fun home near the beach in Longboat Key
  • Vacation Home and Villa
  • 2 stars (Bronze)
  • 2 Bedrooms, Sleeps 6
  • 2 Bathrooms
  • Rates:
    $4295/month - $6995/month
  • Availability:
    Call 800-657-8966

Disclaimer: Coast 2 Coast web sites are designed as a venue for members to present vacation rental properties. We do not accept responsibility for any services provided by any member, business, advertiser or otherwise, listed on this site. By use of any of the information, products and/or services listed throughout this site, the user agrees to hold the administrator of this page, Coast 2 Coast Vacation Rentals, harmless from any consequence which may arise from utilization thereof.

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