Longboat Key holiday homes

We found 11,802 holiday rentals — enter your dates for availability
Discover a selection of 20 homes, 17 apartments and other holiday rentals in Longboat Key that are perfect for your trip. Whether you're going on holiday with family or friends, holiday rentals have the best amenities for hanging out with the people that matter most, which might include Wi-Fi and a hot tub. No matter what you're looking for, you'll be sure to find a property to rent that has what everyone needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – Longboat Key

Showing deals for:6 Nov - 13 Nov

Interior
Four barstools and large area for eating
Living area
Interior
Exceptional
(86 reviews)

Large pool/spa home minutes from beach with arcade games and canal for fishing.

Bradenton

7% off
NZ$4,874
for 7 nights, 1 home
NZ$696 per night
includes taxes & fees
Large pool/spa home minutes from beach with arcade games and canal for fishing.
Gumbo tree in front yard
Quiet spot in paradise
French doors to the lanai and 60 inch TV on the wall.
Have your morning coffee on the lanai.
Exceptional
(92 reviews)

Quiet cozy home near Anna Maria Island, Robinson Preserve, DeSoto Nt’l Monument

Bradenton

7% off
NZ$2,931
for 7 nights, 1 home
NZ$419 per night
includes taxes & fees
Quiet cozy home near Anna Maria Island, Robinson Preserve, DeSoto Nt’l Monument
Living area
Private kitchen
Interior
Interior
Exceptional
(64 reviews)

Waterfront/Kayak with Manatees/Heated Pool/Bikes/Firepit/Fish/close to Beaches

Bradenton

7% off
NZ$5,560
for 7 nights, 1 home
NZ$794 per night
includes taxes & fees
Waterfront/Kayak with Manatees/Heated Pool/Bikes/Firepit/Fish/close to Beaches
Pool
Private kitchen
Dining
Interior
Exceptional
(60 reviews)

Newly Renovated Family Vacation Rental with Pool & Spa

Bradenton

8% off
NZ$3,313
for 7 nights, 1 home
NZ$473 per night
includes taxes & fees
Newly Renovated Family Vacation Rental with Pool & Spa
Terrace/patio
Private kitchen
Living area
Room
Exceptional
(108 reviews)

75 ft Canal Front Anna Maria House, Great for Boaters, Newly Renovated

Anna Maria

8% off
NZ$5,688
for 7 nights, 1 home
NZ$813 per night
includes taxes & fees
75 ft Canal Front Anna Maria House, Great for Boaters, Newly Renovated
Living area
Desk/office space
Pool
Bonus sun room with cute fireplace (non-functional!)
Exceptional
(61 reviews)

Amazing heated pool & spa just minutes from Anna Maria Island

Bradenton

7% off
NZ$3,951
for 7 nights, 1 home
NZ$564 per night
includes taxes & fees
Amazing heated pool & spa just minutes from Anna Maria Island
exercise room in main building
Kitchen renovated Fall 2013/Spring 2014
Room
activity area in main building
Exceptional
(107 reviews)

Palm Bay Club - Bayfront Large 2/2 Condo - Reasonable Price

Siesta Key

6% off
NZ$4,211
for 7 nights, 1 apartment
NZ$602 per night
includes taxes & fees
Palm Bay Club - Bayfront Large 2/2 Condo - Reasonable Price
Beach
Interior
Interior
Room
Exceptional
(30 reviews)

Beach front paradise located in a Condo Building Beach front Penthouse!

Siesta Key

8% off
NZ$7,857
for 7 nights, 1 home
NZ$1,122 per night
includes taxes & fees
Beach front paradise located in a Condo Building Beach front Penthouse!
Fitness facility
Pool
Outdoor dining
Property grounds
Excellent
(155 reviews)

Right on the Waterfront Marina - Suite 117 - 7150 N Tamiami Tail, Sarasota FL

Sarasota

8% off
NZ$1,402
for 7 nights, 1 room
NZ$200 per night
includes taxes & fees
Right on the Waterfront Marina - Suite 117 - 7150 N Tamiami Tail, Sarasota FL
Terrace/patio
Sports court
Interior
Private kitchen
Exceptional
(44 reviews)

Beautiful Blue Beach House Kids & Pets OK Aug, Sept, Oct, Nov, Dec DISCOUNTS! Beautiful Blue Beach House/AMIsland White Sand Beaches

Bradenton

6% off
NZ$2,721
for 7 nights, 1 home
NZ$389 per night
includes taxes & fees
Beautiful Blue Beach House Kids & Pets OK Aug, Sept, Oct, Nov, Dec DISCOUNTS! Beautiful Blue Beach House/AMIsland White Sand Beaches
Private kitchen
Island Time! Bridge St.
Interior
Perfect private outdoor space rain or shine.
Exceptional
(196 reviews)

2 BR 2 Full BA on Anna Maria Island just steps to Beach!

Bradenton Beach

8% off
NZ$4,253
for 7 nights, 1 home
NZ$608 per night
includes taxes & fees
2 BR 2 Full BA on Anna Maria Island just steps to Beach!
Terrace/patio
Private kitchen
Pool
Dining
Exceptional
(62 reviews)

Ila's Beach House: Near IMG-Heated Salt Pool- Pets OK-Modern Organic Smart Home

Bradenton

7% off
NZ$3,613
for 7 nights, 1 home
NZ$516 per night
includes taxes & fees
Ila's Beach House: Near IMG-Heated Salt Pool- Pets OK-Modern Organic Smart Home
Living area
Room
Dining
Children’s area
Exceptional
(24 reviews)

Villa & Garden in Downtown Sarasota ~ Walkable to downtown, 5 Minutes to Beaches

Sarasota

8% off
NZ$3,671
for 7 nights, 1 villa
NZ$524 per night
includes taxes & fees
Villa & Garden in Downtown Sarasota ~ Walkable to downtown, 5 Minutes to Beaches
Dining room seats 8
Fully stocked kitchen perfect for eating at home.
Fully stocked coffee bar includes: loose coffee, K-cups, sugars, and more.
Screened in patio seats 8 at the table. 
Love seat and two swiveled chairs.
Exceptional
(68 reviews)

Ingram House 2

Sarasota

5% off
NZ$3,499
for 7 nights, 1 home
NZ$500 per night
includes taxes & fees
Ingram House 2
Room
Pool
View from room
Outdoor dining
Excellent
(160 reviews)

Sarasota “Executive Waterfront Suite” A hotel rm # 103 on Sara Bay Marina

Sarasota

8% off
NZ$1,421
for 7 nights, 1 room
NZ$203 per night
includes taxes & fees
Sarasota “Executive Waterfront Suite” A hotel rm # 103 on Sara Bay Marina
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Why visit Longboat Key

  • Pristine Beaches: Enjoy the tranquil and beautiful beaches, perfect for sunbathing, swimming, and leisurely walks along the shore.
  • Outdoor Activities: Engage in water sports, fishing, and boating at the local marina, making the most of the stunning waterways.
  • Serene Parks: Relax in urban parks, ideal for picnics and enjoying the natural beauty of Longboat Key.
  • Stunning Sunsets: Witness breathtaking sunsets that create a picturesque backdrop for a perfect evening.
  • Vibrant Culture: Immerse yourself in the friendly atmosphere and local culture, making for a memorable holiday experience.

Top attractions near Longboat Key

Longboat Key, Florida, is a picturesque destination perfect for beach lovers and families alike. Visitors can enjoy stunning beaches, explore the local marina, and relax in urban parks, all while soaking up the vibrant culture. This charming locale offers a variety of outdoor activities and experiences, making it an ideal spot for those seeking sun, sea, and relaxation. Whether you're swimming, walking along the shore, or enjoying a picnic in the park, Longboat Key has something for everyone.

  • Lido Beach: Embrace the relaxed beach vibes with golden sands and gentle waves, a perfect escape for sun-seekers, located 14km away.
  • St. Armands Circle: Enjoy the lively city vibes along this bustling street, offering a blend of boutique shops and local eateries, situated 13km away.
  • Longboat Key Beaches: Discover a charming townNeighbourhood with city vibes, providing a scenic coastal retreat merely 5km away.

Things to do recommended for couples

Looking for a romantic escape in Longboat Key? Enjoy a sunset walk along the pristine beaches, hand in hand, and savour local seafood delicacies at a quaint waterfront restaurant. Let the serene coastal charm set the mood for your memorable getaway.

Things to do recommended for families

Families visiting Longboat Key can enjoy the stunning beaches and explore the Longboat Key Turtle Watch, where kids can learn about sea turtles. The nearby Mote Marine Laboratory offers interactive exhibits and touch tanks, perfect for an engaging family day out.

Things to do recommended for groups

Explore the stunning beaches of Longboat Key, enjoy a group kayak tour through the mangroves, or indulge in a sunset cruise. Don't miss out on the local seafood dining experiences that showcase fresh catches from the Gulf of Mexico.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Longboat Key

If you're travelling with a group, family, pets, or planning an extended stay, it's important to filter your options according to your specific needs. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Longboat Key with a group: Consider how many bedrooms you'll require, alongside facilities like a full kitchen or outdoor area for a group get-together. Luckily, you can use filters for all of these features, and more, on Vrbo.
  • Traveling to Longboat Key with young kids: Traveling with young children can be tough. You must prioritise their comfort and safety, along with ensuring they have access to age-appropriate facilities like a private swimming pool. It’s also wise to think about how close you are to attractions that are family-friendly.
  • Taking your pets with you to Longboat Key: For many, a family holiday isn’t complete without including their furry companion. If this resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly properties offer feeding bowls and beds, ensuring everyone feels right at home.
  • Planning for a long term stay visiting Longboat Key: If you're seeking holiday rentals with special offers for extended stays of a month or more, you've come to the right place. By applying the proper filters, you can effortlessly discover and save on monthly rentals. Think about including options like a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay near Longboat Key

Longboat Key, Florida, is a tranquil island paradise perfect for a family holiday or a relaxing beach getaway. With its pristine, quiet beaches and stunning sunsets, visitors can immerse themselves in the natural beauty and friendly atmosphere of this charming locale. Enjoy leisurely strolls along the shoreline, partake in water activities, or simply unwind in the serene surroundings, making Longboat Key an ideal destination for those seeking a peaceful escape.

  • Sarasota: Situated 14km from Longboat Key, Sarasota offers a dynamic blend of city sophistication and coastal charm. Visitors delight in the urban buzz alongside scenic, family-friendly beaches. The city is renowned for its accessible shopping centres and vibrant town neighbourhoods, making it a perfect destination for a beach holiday with a touch of metropolitan flair.
  • Anna Maria Island: Only 11km away, Anna Maria Island is an idyllic natural retreat. This island destination beckons travellers with its pristine family beaches and outdoor adventures. Enjoy the ease of reaching recreational areas and shopping centres, while the captivating cape and coastal landscapes provide endless opportunities for exploration and relaxation.
  • Bradenton Beach: At a mere 8km from Longboat Key, Bradenton Beach is a vibrant coastal city that combines the allure of sun-kissed beaches with a family-oriented outdoor experience. Its proximity to town neighbourhoods and recreational areas enhances the appeal, making it an excellent spot for those seeking both a lively beach atmosphere and a chance to explore local attractions.

Best time to go to Longboat Key

If you're planning a trip to Longboat Key, it's a good idea to check both the weather and property rates. The warmest month is August.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January62.6°F (17.0°C)Light RainMostly SunnyAverage
February65.5°F (18.6°C)No Rain (Dry)Mostly SunnyAverage
March68.4°F (20.2°C)Light RainMostly SunnyModerately High
April73.8°F (23.2°C)Light RainMostly SunnyModerately High
May78.1°F (25.6°C)Light RainMostly SunnyAverage
June82.0°F (27.8°C)Light RainMostly SunnyAverage
July83.1°F (28.4°C)Moderate RainMostly SunnyModerately High
August83.5°F (28.6°C)Moderate RainMostly SunnyAverage
September81.5°F (27.5°C)Moderate RainMostly SunnyAverage
October77.0°F (25.0°C)Light RainMostly SunnyModerately Low
November70.5°F (21.4°C)Light RainMostly SunnyModerately Low
December66.4°F (19.1°C)Light RainMostly SunnyModerately Low

Booking with Vrbo is a breeze

Looking to save on your next adventure? Consider being flexible with your travel dates, as prices can fluctuate. Plus, extending your stay often results in significant savings. To discover the ideal Vrbo property that fits your budget, utilise our filters to search by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board offers a handy space where you can create fresh trips, resume planning from where you left off, or review and organise your travel plans. You’ll also see any properties you’ve saved or booked, neatly grouped under Potential, Upcoming, or Current Trips. To begin using Trip Boards, simply visit: https://www.bookabach.co.nz/trips.

**Based on Vrbo properties bookings.

Relaxing Longboat Key will entice you

Enjoy the monuments and other features of Longboat Key. This relaxing city is known for its beaches, bird watching and seaside. Siesta Key Beach and Lido Beach are just a couple of the must-see attractions in the area. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in and around Longboat Key

Are you hoping to find things to do during your stay? Venture out of your cosy holiday rental and experience everything that Longboat Key has to offer. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Sarasota Jungle Gardens (7.1 mi / 11.4 km)
  • Mote Marine Laboratory & Aquarium (7.4 mi / 12 km)
  • Premier Sports Campus at Lakewood Ranch (16.9 mi / 27.3 km)
  • Aluna Wellness Center & Spa (5.3 mi / 8.6 km)
  • Harborside Golf Course at Longboat Key Club (6.9 mi / 11.2 km)
  • Links on Longboat (7 mi / 11.2 km)

Exploring the beaches and other natural features in Longboat Key

Travellers enjoy Longboat Key for its sunsets and seaside. Whether you're an adventurous traveller or just want to take in the scenery, you'll be sure to find the perfect setting for your holiday in Longboat Key. These are some of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

  • Siesta Key Beach (12 mi / 19.4 km)
  • Lido Beach (8.8 mi / 14.2 km)
  • Fort De Soto Park (15.8 mi / 25.4 km)
  • Tampa Bay (25.2 mi / 40.6 km)
  • Jewfish Key (2.5 mi / 3.9 km)
  • Longboat Key Beaches (2.8 mi / 4.6 km)

Seasonal weather averages in Longboat Key

Travellers enjoy Longboat Key for its boating. If you're hoping to enjoy some warm-weather activities on your holiday, August, July, June and September are the hottest months to visit, when temperatures average 28°C.

How to get to and around Longboat Key

The nearest airport is in Sarasota, FL (SRQ-Sarasota-Bradenton Intl.), located 6.7 mi (10.8 km) from the city centre. If you're unable to find a flight that fits your schedule, you could book a flight to St. Petersburg, FL (SPG-Albert Whitted), which is 24.4 mi (39.2 km) away.

Frequently asked questions

What is the most popular type of holiday home accommodation in Longboat Key?
Condos are the most popular type of holiday home in Longboat Key, according to our data. Even if you have a different idea about what you want, Bookabach has holiday homes in a variety of shapes and sizes. Take a look at our options to find your ideal match.
How much does it cost to rent a holiday home in Longboat Key?
Length of stay, season and property type are some things that can determine the price of a holiday home. Simply enter your dates of travel to find your ideal match. From comfy cabins to expansive luxury villas, all Bookabach holiday homes offer incredible value.
How much does it cost to rent a beach house in Longboat Key?
Prices for beach houses in Longboat Key differ depending on the size and type of the property and time of year you're travelling. Just enter your travel dates into Bookabach and how many guests to view your home options and prices. From there you can use our filters to narrow your search by amenities, ratings, nearby activities and more.
What are popular home amenities in Longboat Key?
A sauna, a beach view and tennis rank as the most popular home amenities in Longboat Key. Whether you plan to go as a party of one, with your sweetheart or as a family group, Bookabach will help you find a holiday home that suits your tastes with all the conveniences you're looking for.
What are the top attractions for families in Longboat Key?
There are loads of cool things to do and see with the family in Longboat Key, including:
  • Coquina Beach
  • Cortez Beach
  • Manatee Public Beach
Can I find two-bedroom holiday homes in Longboat Key?
Longboat Key has 135 two-bedroom holiday homes that you can choose from. Discover a holiday home with all the comfort and privacy you want at a price you'll love on Bookabach.
Are there holiday homes with WiFi in Longboat Key?
You can pick from 94 holiday homes with WiFi in Longboat Key. If you want to disconnect from daily life while on holiday, but still want to be connected to the web, these getaways have just what you need. Narrow your search by applying the WiFi filter on Bookabach.
How old do you have to be to rent a holiday home in Longboat Key?
The age limit can vary across properties on Bookabach, so be sure to check the rules of the holiday home in Longboat Key you want to book. But normally, it's 16, 18 or 21.
How long can I rent a holiday home in Longboat Key for?
How long you can book a holiday home in Longboat Key depends on the property. Just enter your desired travel dates to look at a list of options offering extended stays. With plenty of amenities such as air conditioning and kitchens, as well as some offering weekly or monthly discounts, you're sure to get someplace just right to call your home away from home in Longboat Key.

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