Longboat Key is situated between the Gulf of Mexico and Sarasota Bay. It’s an attractive destination for those who wish to witness spotless natural beauty in a peaceful environment. A must-visit attraction is Beer Can Island, a national natural landmark made by oceanic streams. Quick Point Nature Preserve is the spot to visit if you’re looking to go hiking and bird-watching. For a more relaxed experience, visit Joan M Durante Community Park, which has a playground for children. We are certain that once you arrive at Longboat Key, you will not want to leave because of its surreal beauty. Planning a trip here? Read on to find a list of the best monthly rentals in Longboat Key, Florida.
We handpicked these listings carefully, considering (wherever possible) host status, recent guest reviews, location, accommodation type, prices, decor, availability of dates, and long-term stay rules and regulations. The image galleries get refreshed with the latest updates regularly. They were last updated on April 14, 2024.
1. Luxurious beachfront villa with a private pool (from USD 159)
This elegant rental will provide easy access to the Gulf of Mexico, and it’s a few steps from a secluded beach where you can leisurely enjoy the waves. Guests have access to a heated shared pool and hot tub to enjoy complete relaxation on their vacation. For indoor entertainment, you can use the television with satellite or cable and enjoy your favorite movies or surf the internet with Wi-Fi.
Enjoy a discount of 50 percent for booking this rental for 28 nights or longer.
2. Welcoming villa with Wi-Fi (from USD 488)
Located on the picturesque Gulf of Mexico, this beach house is constructed in the mid-century modern style and boasts a spacious floor plan. The rear deck opens onto the private beach, and spectacular water views can be enjoyed from almost every room here. Moreover, high-speed Wi-Fi will keep you well-connected to the outside world, and the smart TV and DVD player will keep you thoroughly entertained.
The host offers a discount of 25 percent for staying 30 nights or longer.
Top guest reviews
Cleanliness:
the house was very clean when we arrivedeverything was so clean and comfortableit was very clean roomy and the kitchen was fully stocked with everything you will needit is very nicely appointed with very clean lines and tasteful furniturethis house was clean & the beach was completely privateHost:
the owner was very responsiveRead more reviewsLocation:
the location of the house is perfectthe location is wonderful i have never been so close to the beachsunsets were beautiful and the location was quiet and secludedwe saw dolphins the location is perfect the house beautiful i wouldn’t change a thingnice publix very close— you could walk there if you had to
3. Beautiful island home with a private dock (from USD 1658)
Enjoy a discount of 27 percent by booking this place for 28 nights or more. This house is set in a gorgeous 2-acre (0.81-hectare) property where one can witness several species of birds and sometimes even marine life. The waters around this rental are filled with fish, making this place an ideal choice for fishing enthusiasts.
The home also has a private dock, so you can get your boat or rent one from nearby Cannons Marina on Longboat Key.
4. Amazing condo with a fully equipped kitchen (from USD 227)
This stunning condo boasts breathtaking views of Sarasota Bay and is just a short walk to the beach. Since the rental is located in the Harbor Villa Club community, guests can enjoy the facilities such as a heated shared pool, tennis courts, and a spa. Moreover, the house has a fully equipped kitchen where you can whip up delicious food and a dining table to relish it. Lounge comfortably in the spacious living room and watch your favorite movie on the TV.
Further, the host discounts the price by 15 percent if you stay for 28 nights or more.
Top guest reviews
Cleanliness:
very clean and comfortableRead more reviewsLocation:
beautiful location and outstanding accommodations
Superhost
5. Waterfront house with a private hot tub (from USD 675)
This stunning home will charm you with its luxurious furnishings and spacious floor plan. The master bath features a hot tub, offering beautiful views of the canal, and you can also use the heated private pool for an additional fee. Access the water through the property’s private dock and use the kayaks and paddle boards available here for free.
This rental offers a monthly discount of 10 percent if you book it for 28 nights or more.
6. Comfortable condo with amazing views (from USD 349)
This charming condo is in the Beach Resort, the perfect seaside paradise with palm trees, tropical plants, and manicured gardens. It boasts a private balcony overlooking the beautiful ocean where you can unwind with a glass of your favorite drink and watch the dolphins swim.
Cook your favorite meal in the kitchen and relish it on the cozy dining table. Moreover, guests can avail of a 12 percent discount if they book this place for a minimum of 28 nights.
7. Sunny Side Up (from USD 250)
Avail a discount of 20 percent on staying at this restored beach cottage for 28 nights or more. This rental is minutes away from St. Armands Circle where you can indulge in unlimited shopping, and Whitney Beach for fun in the sea. Enjoy outdoor activities around the cottage, such as kayaking, jet skiing, fishing, boating, and more. Plus, those working remotely will be grateful for the available Wi-Fi, and home chefs will be delighted upon seeing the fully equipped kitchen.
8. Gorgeous beach house with a deck (from USD 252)
This rental is perfect for those who love indoor-outdoor living. It features a deck with outdoor furniture and a grill, as well as an outdoor area with a fire pit. The property features a living room with a television and a fully equipped kitchen that is tastefully decorated. Moreover, beach lovers can hop to the shore or nearby restaurants, as everything is five minutes away.
Planning a long-term stay here? You can avail a monthly discount of 10 percent if you book this place for 28 nights or more.
Top guest reviews
Cleanliness:
house was super cute and clean clara was a great host 10/10Read more reviewsLocation:
really sweet beach house with a nice florida vibe in a super convenient location
9. Delightful home with access to tennis courts (from USD 130)
Enjoy the facilities of a tennis resort by choosing this lovely rental surrounded by dolphins, turtles, gorgeous beaches, and exciting nightlife. The accommodation is next to 10 tennis courts where you can play fun games and a bar and restaurant to enjoy after a long day. For those fond of the water, a junior-size Olympic pool is available here where you can swim laps. Further, you can whip up scrumptious meals in the fully equipped kitchen with a coffee maker and dishwasher.
Plan an extended stay, as there is a monthly discount of five percent if you book this property for 28 nights or more.
Top guest reviews
Amenities & Room:
there are tennis courts of course and an excellent pool literally right out the doorCleanliness:
not to mention top-notch appliances immaculately cleaned super comfy bed and lots of spacethis place was nicely appointed well equipped clean quiet and an easy walk to the beachHost:
the people in the club room are professional friendly and helpfulbut the especially outstanding factor in this rental is richard the hostrichard is friendly and quick to respond with any issuesRead more reviewsLocation:
and very close a few minutes walk to a truly beautiful soft white sand beachloved quiet pool gym and beach was close and beautiful
10. Beautiful home with an outdoor pool (from USD 463)
This lovely vacation home is perched on a 1-acre (0.40-hectare) lawn surrounded by the natural beauty of Joan M Durante Community Park. You can also walk to the beach from here and enjoy the waves and stunning views. If you wish to chill on the property, take a relaxing dip in the private pool or unwind on the private porch.
Earn a two percent discount on booking the property for 28 nights or more.
Top guest reviews
Amenities & Room:
there are comfortable tables and chairs around the pool & grillif you love to cook the kitchen is complete with all necessary utensils and small appliancesreally enjoyed the pool and the peaceful evenings on the deckthe televisions and internet worked great which came in handy for my son who brought his play stationthe backyard is fenced for pool/hot tub privacy and safety for your dogCleanliness:
great property very clean and well appointedthe villa was very clean it contained every kitchen supply neededthe property was great and extremely cleanthe property was very clean and well furnished; we cooked most mealsHost:
david was very responsive and helpfuldavid was extremely communicative and friendlyit was a joy working with the hostthe owner is very nice and available if you need himthe host has outside lights on timers which make returning after sunset welcomingRead more reviewsLocation:
it is walking distance to a few great restaurantsit's a short walk to beautiful beach and backs up to a really nice parkthe beach is close by or you can stay right at the house and enjoy the poolwe couldn't ask for more beach was awesome walking distance to great restaurantsthe beautiful beach is just a short walk from the house
Fish, swim or hike in Longboat Key
From unending beach days to spectacular views, Longboat Key will have something for everyone. So, choose a rental from the list above and enjoy monthly discounts and excellent amenities.
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