Longboat Key Accommodations

Check out Owner Direct Vacation Rentals to view and book your accommodations in Longboat Key, Florida. Florida offers a fantastic vacation experience at any time of year, known for their warm weather and sunny skies. A vacation rental accommodation in Longboat Key provides all the amenities of home, plus a few luxuries to enjoy your vacation in style. Why not book a condo rental or villa... read more
Check out Owner Direct Vacation Rentals to view and book your accommodations in Longboat Key, Florida. Florida offers a fantastic vacation experience at any time of year, known for their warm weather and sunny skies. A vacation rental accommodation in Longboat Key provides all the amenities of home, plus a few luxuries to enjoy your vacation in style. Why not book a condo rental or villa rental in this charming town in central-west Florida?

A villa rental or condo rental in Longboat Key offers a touch of class to your vacation experience. Located south of Anna Maria Island, between Sarasota Bay and the Gulf of Mexico, Longboat Key is the perfect location for your vacation rental lodging. Condo rentals, villa rentals and other accommodations can have various options that include tennis courts, swimming pools, and sea views. Longboat Key has a variety of restaurants to suit every palate, from lobster to international flavours, some with lovely ocean views. The downtown area is an excellent destination to enjoy an afternoon out, with boardwalks, cafes and boutique shops.

Villas in Longboat Key are the ideal way to enjoy some of the area’s unforgettable beaches. With white sand beaches and crystal clear ocean waters, a variety of water activities can be enjoyed in Longboat Key. The beaches are home to turtle and seabird nesting sites, providing some excellent wildlife viewing options for travellers. Scuba diving and snorkelling trips in the area provide an opportunity to explore the underwater world, with colourful fish, turtles and other sights. Explore Owner Direct’s extensive website to view a variety of villa rentals and condo rentals to suit every budget in Longboat Key.

Enjoy the friendly town of Longboat Key, Florida with an accommodation from your partner in travel, Owner Direct Vacation Rentals. Vacation rentals in Longboat Key, Florida offer your choice of condo rental or villa rental to ensure an unforgettable vacation.

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  • Beachfront Condo with

    Turtle Crawl Inn: Condo in a hotel
    1 BDR • 1 BA • Sleeps 6 • #237418
    208 to 302 USD/night
    Gulf view in Turtle Crawl Inn. Resort on Longboat Key, FL View. View. View. Welcome to our condo hotel. Our onsite office with friendly staff is here to help you with all of your needs. With vacation our condo you’ll escape to our Tropical Paradise with 200 feet of beautiful beach and awesome sunsets. This one bedroom Condo on the fourth floor with a private balcony is the place to enjoy the sound of the rolling waves and some of the most spectacular sunsets on Longboat Key. This unit located in the Tower overlooking the Gulf of Mexico is bright and spacious; it has a Queen and Double beds in the bedroom and a Queen Sleeper sofa in the living room for that extra guest. It has a fully equipped kitchen, Cable TV, dining area, and living room sliding glass doors the complete width of your condo, making it easy to enjoy the beach view. With the use of our elevator, you just step away from the heated pool, beach and other community amenities.
  • Beachfront Condo with

    Turtle Crawl Inn: Condo in a hotel
    1 BDR • 1 BA • Sleeps 6 • #251646
    208 to 302 USD/night
    Gulf view in Turtle Crawl Inn. Resort on Longboat Key, FL View. View. View. Welcome to our condo-hotel. Our onsite office with friendly staff is here to help you with all of your needs. With vacation our condo you’ll escape to our Tropical Paradise with 200 feet of beautiful beach and awesome sunsets. This one-bedroom condo on the third floor with a private balcony is the place to enjoy the sound of the rolling waves and some of the most spectacular sunsets on Longboat Key. This unit located in the Tower overlooking the Gulf of Mexico is bright and spacious; it has 2 Queens beds in the bedroom and a Double Sleeper Sofa and Queen Murphy bed in the living room for that extra guest. It has a fully equipped kitchen, Cable TV, dining area, and living room sliding glass doors the complete width of your condo, making it easy to enjoy the beach view. With the use of our elevator, you just step away from the heated pool, beach and other community amenities.
  • Harbor Villa Club Unit 308

    Longboat Key: Vacation Rental
    2 BDR • 2 BA • Sleeps 4 • #256332
    284 to 423 USD/night
    Harbor Villa Club is Longboat Key's best kept secret! Enjoy the peace and quite with breathtaking views of Sarasota Bay.. The Harbour Villa’s are just a 3-minute drive to the north end of the key home to the historic Longbeach Village, known in its earlier days as a transient fishing village. While taking a stroll through this neighborhood your likely to see peacocks on roofs or resting in someone’s yard. It is also a great place for dinner with a view, with options for waterfront restaurants such as the rustic Mar Vista or the more modern Shore. The north end of the key also holds a hidden gem known as Beer Can Island. Erosion has uprooted many of the Australian pines trees here giving it a deserted island feel, a great place worth exploring. 3 minutes in the other direction will put you at Harry’s your local corner store since 1979. Harry’s also has both a deli and an upscale restaurant behind the store, so you have options for whatever you’re in the mood for. Looking to go for a hike? Joan M. Durante Community Park is a 3-minute drive south and has excellent walking trails through the mangroves with portions that overlook the bay. There is a lot of wildlife to see here and a small park out front for children. Mote Marine Laboratory & Aquarium is also a great place to visit if you are interested in marine life. There are many actives to enjoy on the key as well such and Paddle boarding, Kayaking, and golf. Longboat Key charters offers sightseeing/ecotours, fishing, and sunset tours. The south end of longboat meets At. Armand’s Circle which has a great mix of restaurants, bars, and unique shops. The north end of the island runs into Anna Maria Island which is a hub of entertainment as well.
  • CANCELLATION SPECIAL

    Longboat Key: Vacation Rental
    2 BDR • 2 BA • Sleeps 6 • #256333
    189 to 244 USD/night
    Harbor Villa Club is Longboat Key's best kept secret! Enjoy the peace and quite with breathtaking views of Sarasota Bay.. The Harbour Villa’s are just a 3-minute drive to the north end of the key home to the historic Longbeach Village, known in its earlier days as a transient fishing village. While taking a stroll through this neighborhood your likely to see peacocks on roofs or resting in someone’s yard. It is also a great place for dinner with a view, with options for waterfront restaurants such as the rustic Mar Vista or the more modern Shore. The north end of the key also holds a hidden gem known as Beer Can Island. Erosion has uprooted many of the Australian pines trees here giving it a deserted island feel, a great place worth exploring. 3 minutes in the other direction will put you at Harry’s your local corner store since 1979. Harry’s also has both a deli and an upscale restaurant behind the store, so you have options for whatever you’re in the mood for. Looking to go for a hike? Joan M. Durante Community Park is a 3-minute drive south and has excellent walking trails through the mangroves with portions that overlook the bay. There is a lot of wildlife to see here and a small park out front for children. Mote Marine Laboratory & Aquarium is also a great place to visit if you are interested in marine life. There are many actives to enjoy on the key as well such and Paddle boarding, Kayaking, and golf. Longboat Key charters offers sightseeing/ecotours, fishing, and sunset tours. The south end of longboat meets At. Armand’s Circle which has a great mix of restaurants, bars, and unique shops. The north end of the island runs into Anna Maria Island which is a hub of entertainment as well.
  • Come Stay at Harbor Villa

    Longboat Key: Vacation Rental
    2 BDR • 2 BA • Sleeps 4 • #256352
    140 to 295 USD/night
    Harbor Villa Club is Longboat Key's best kept secret! Enjoy the peace and quite with breathtaking views of Sarasota Bay.. The Harbour Villa’s are just a 3-minute drive to the north end of the key home to the historic Longbeach Village, known in its earlier days as a transient fishing village. While taking a stroll through this neighborhood your likely to see peacocks on roofs or resting in someone’s yard. It is also a great place for dinner with a view, with options for waterfront restaurants such as the rustic Mar Vista or the more modern Shore. The north end of the key also holds a hidden gem known as Beer Can Island. Erosion has uprooted many of the Australian pines trees here giving it a deserted island feel, a great place worth exploring. 3 minutes in the other direction will put you at Harry’s your local corner store since 1979. Harry’s also has both a deli and an upscale restaurant behind the store, so you have options for whatever you’re in the mood for. Looking to go for a hike? Joan M. Durante Community Park is a 3-minute drive south and has excellent walking trails through the mangroves with portions that overlook the bay. There is a lot of wildlife to see here and a small park out front for children. Mote Marine Laboratory & Aquarium is also a great place to visit if you are interested in marine life. There are many actives to enjoy on the key as well such and Paddle boarding, Kayaking, and golf. Longboat Key charters offers sightseeing/ecotours, fishing, and sunset tours. The south end of longboat meets At. Armand’s Circle which has a great mix of restaurants, bars, and unique shops. The north end of the island runs into Anna Maria Island which is a hub of entertainment as well.
  • Bayfront unit with a

    Longboat Key: Vacation Rental
    2 BDR • 2 BA • Sleeps 4 • #258635
    189 to 244 USD/night
    Harbor Villa Club is Longboat Key's best kept secret! Enjoy the peace and quite with breathtaking views of Sarasota Bay.. Come enjoy some peace in quiet in beautiful Longboat Key. This clean and comfortable 2 bedroom 2 bathroom condo on Sarasota bay is perfect for a relaxing getaway. You can have the perfect vacation without even leaving this condo complex! We hope you have the opportunity to enjoy some of the unique features of this beautiful unit: • Carefree check-in, go straight to your unit no office visit required. • Fully Equipped Kitchen including microwave, stove, dishwasher, fridge, and coffee maker. • Dining Room Table that’s seats four. • Bright and cozy living room area w/ a large flat screen TV. • Washer and Dryer Conveniently located in unit. • Master bedroom with a king size bed, flat screen TV, walk in shower, walk in closet, and beautiful view of the bay! • Spacious guest bedroom with two twin beds and guest bath with walk in shower. • Large Patio overlooking the bay with outdoor seating and a table. Harbor Villa Club amenities • Pool • Hot Tub • Tennis Court • Boat Slips (Rented Separately) • Covered Parking • Elevators Surrounding Area The Harbour Villa’s are just a 3-minute drive to the north end of the key home to the historic Longbeach Village, known in its earlier days as a transient fishing village. While taking a stroll through this neighborhood your likely to see peacocks on roofs or resting in someone’s yard. It is also a great place for dinner with a view, with options for waterfront restaurants such as the rustic Mar Vista or the more modern Shore. The north end of the key also holds a hidden gem known as Beer Can Island. Erosion has uprooted many of the Australian pines trees here giving it a deserted island feel, a great place worth exploring. 3 minutes in the other direction will put you at Harry’s your local corner store since 1979. Harry’s also has both a deli and an upscale restaurant behind the store, so you have options for whatever you’re in the mood for. Looking to go for a hike? Joan M. Durante Community Park is a 3-minute drive south and has excellent walking trails through the mangroves with portions that overlook the bay. There is a lot of wildlife to see here and a small park out front for children. Mote Marine Laboratory & Aquarium is also a great place to visit if you are interested in marine life. There are many actives to enjoy on the key as well such and Paddle boarding, Kayaking, and golf. Longboat Key charters offers sightseeing/ecotours, fishing, and sunset tours. The south end of longboat meets At. Armand’s Circle which has a great mix of restaurants, bars, and unique shops. The north end of the island runs into Anna Maria Island which is a hub of entertainment as well.
  • Book Now! Harbor Villa

    Longboat Key: Vacation Rental
    2 BDR • 2 BA • Sleeps 4 • #256351
    150 to 231 USD/night
    Harbor Villa Club is Longboat Key's best kept secret! Enjoy the peace and quite with breathtaking views of Sarasota Bay.. The Harbour Villa’s are just a 3-minute drive to the north end of the key home to the historic Longbeach Village, known in its earlier days as a transient fishing village. While taking a stroll through this neighborhood your likely to see peacocks on roofs or resting in someone’s yard. It is also a great place for dinner with a view, with options for waterfront restaurants such as the rustic Mar Vista or the more modern Shore. The north end of the key also holds a hidden gem known as Beer Can Island. Erosion has uprooted many of the Australian pines trees here giving it a deserted island feel, a great place worth exploring. 3 minutes in the other direction will put you at Harry’s your local corner store since 1979. Harry’s also has both a deli and an upscale restaurant behind the store, so you have options for whatever you’re in the mood for. Looking to go for a hike? Joan M. Durante Community Park is a 3-minute drive south and has excellent walking trails through the mangroves with portions that overlook the bay. There is a lot of wildlife to see here and a small park out front for children. Mote Marine Laboratory & Aquarium is also a great place to visit if you are interested in marine life. There are many actives to enjoy on the key as well such and Paddle boarding, Kayaking, and golf. Longboat Key charters offers sightseeing/ecotours, fishing, and sunset tours. The south end of longboat meets At. Armand’s Circle which has a great mix of restaurants, bars, and unique shops. The north end of the island runs into Anna Maria Island which is a hub of entertainment as well.
  • Longboat Key, Waterfront

    Longboat Key: Vacation Rental
    3 BDR • 2 BA • Sleeps 6 • #245570
    348 to 348 USD/night
    Nestled on a gorgeous canal in scenic Longboat Key, this waterfront 3BR/2BA home is the quintessential Gulf getaway. Take a dip in the private pool or spa within the screened porch. Afterward, head out to open waters for a sunset cruise. Sleeps 6.. Get the most out of your Gulf vacation at this waterfront 3BR/2BA home. A private pool and spa set within a completely enclosed patio make it a delight to take a dip and relax in the sun. When evening falls, head to the dock to enjoy the golden hour by the canal. Within a half-mile walk of luxurious Silver Sands Gulf Beach, you’ll have the sand between your toes in no time. LIVING AREAS Serving as the social hub of the home, the spacious and bright living room is the perfect place to spend quality time with friends and family. Furnished with a sofa, love seat, and two armchairs, you’ll find plenty of comfy seating to settle in for a night of old-school fun with a board game. Kick back on the sofa and armchair in the second living room to watch a movie on the 55” TV. KITCHEN & DINING With stainless steel appliances and a pass-through window to the back patio, you’ll love concocting gourmet meals in the kitchen. Whether you’re baking fresh rolls or frying up the catch of the day, set your masterpiece at the four-person dining table. BEDROOMS & BATHS This single-story home comfortably sleeps up to six guests across the three bedrooms, all of which are appointed with hotel-quality linens. Two full bathrooms are each stocked with a complimentary starter supply of toiletries and bath amenities. The master bedroom features a king bed, vanity, walk-in closet, and 43” TV. In the en-suite bathroom, you’ll find a tiled walk-in shower. The second bedroom is furnished with a full-size bed and 43” TV, while the third bedroom offers another full-size bed. The guest bathroom is complete with a walk-in shower and a separate jetted tub. OUTDOOR AREAS Experience the Gulf in style on the expansive screened patio. Enjoy lunch at the four-person patio table or snack on hors-d'oeuvres at the two-person bar. Afterward, kick back in one of the outdoor loungers for an afternoon siesta. Cool off in the private pool or soak in the spa. A massive lawn leads to the private dock. (Please note that the boat lift on the dock is not available for guest use.) EXTRA AMENITIES & DETAILS Driveway parking is available for two vehicles (RV and trailer parking is not permitted). Additional amenities include complimentary Wi-Fi, cable TV, a washer/dryer, beach chairs, and two bicycles. Please note that a $10 per day utility fee will be added to your rent if you would like the pool heated during your stay. THE LOCATION Your home is situated in the enchanting neighborhood of Emerald Harbor. Overlooking a gorgeous wide canal, your rental affords a serene setting on the north end of Longboat Key. For a fun outing, hop on one of the provided bikes and cycle to Silver Sands Gulf Beach where you can splash in the waves and try your hand at lawn bowling. Rent a kayak and explore the many inlets and canals in the area. Make sure to bring a fishing pole and cast a line for some phenomenal Florida fishing. Or hire a boat from Catherine’s Florida Charters for a day of snorkeling and dolphin spotting or a sunset cruise. Upon arrival, easily access your home with a keyless secure door code; no need for an in-person key exchange. Your rental will be professionally cleaned and ready for you to enjoy. You can expect all the comforts of a fine hotel, including shampoo, soaps, paper products, and linens. The HomeDroid tablet (an electronic guest directory) will be provided with specific home details, Wi-Fi access, and TV instructions. If you need anything before, during, or after your stay, our 24/7 local team is ready to help!
  • Harbor Villa Club Unit 205

    Longboat Key: Vacation Rental
    2 BDR • 2 BA • Sleeps 4 • #256242
    189 to 332 USD/night
    Harbor Villa Club is Longboat Key's best kept secret! Enjoy the peace and quite with breathtaking views of Sarasota Bay.. The Harbour Villa’s are just a 3-minute drive to the north end of the key home to the historic Longbeach Village, known in its earlier days as a transient fishing village. While taking a stroll through this neighborhood your likely to see peacocks on roofs or resting in someone’s yard. It is also a great place for dinner with a view, with options for waterfront restaurants such as the rustic Mar Vista or the more modern Shore. The north end of the key also holds a hidden gem known as Beer Can Island. Erosion has uprooted many of the Australian pines trees here giving it a deserted island feel, a great place worth exploring. 3 minutes in the other direction will put you at Harry’s your local corner store since 1979. Harry’s also has both a deli and an upscale restaurant behind the store, so you have options for whatever you’re in the mood for. Looking to go for a hike? Joan M. Durante Community Park is a 3-minute drive south and has excellent walking trails through the mangroves with portions that overlook the bay. There is a lot of wildlife to see here and a small park out front for children. Mote Marine Laboratory & Aquarium is also a great place to visit if you are interested in marine life. There are many actives to enjoy on the key as well such and Paddle boarding, Kayaking, and golf. Longboat Key charters offers sightseeing/ecotours, fishing, and sunset tours. The south end of longboat meets At. Armand’s Circle which has a great mix of restaurants, bars, and unique shops. The north end of the island runs into Anna Maria Island which is a hub of entertainment as well.

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