Longboat Key holiday rentals

We found 11,806 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:13 Nov - 20 Nov

Property grounds
Marina
Private kitchen
Pool
Exceptional
(72 reviews)

Relaxing Lakefront Home: 3BR/2BA, Heated Pool, Near Siesta Key Beach

Sarasota

7% off
AU$3,037
for 7 nights, 1 home
AU$434 per night
includes taxes & fees
Relaxing Lakefront Home: 3BR/2BA, Heated Pool, Near Siesta Key Beach
Living area
Desk/office space
Large dinning room
Bonus sun room with cute fireplace (non-functional!)
Exceptional
(61 reviews)

Amazing heated pool & spa just minutes from Anna Maria Island

Bradenton

7% off
AU$3,239
for 7 nights, 1 home
AU$463 per night
includes taxes & fees
Amazing heated pool & spa just minutes from Anna Maria Island
Exterior
Pool
Property grounds
Living area
Exceptional
(136 reviews)

6 Bedrooms - Waterfront,pool, dock, great for families. Big yard, lots of room.

Bradenton

8% off
AU$10,951
for 7 nights, 1 home
AU$1,564 per night
includes taxes & fees
6 Bedrooms - Waterfront,pool, dock, great for families. Big yard, lots of room.
Interior
Private kitchen
Living area
Living area
Exceptional
(64 reviews)

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

Bradenton

7% off
AU$4,507
for 7 nights, 1 home
AU$644 per night
includes taxes & fees
Waterfront/Kayak with Manatees/Heated Pool/Bikes/Firepit/Fish/close to Beaches
Front Wrought Iron Private Gates Entering- “Sea La Vie” Pond, Meditation Garden.
Longboat Pass
Take An Incredible Stroll Through The Ringling Museum In Sarasota!
Private Swimming Pool & Relaxing Area.
Exceptional
(83 reviews)

Heated Pool~Massive Spanish Home~Water Views~Sunset Deck~Grill~WIFI~Near Beaches

Bradenton

8% off
AU$6,900
for 7 nights, 1 home
AU$986 per night
includes taxes & fees
Heated Pool~Massive Spanish Home~Water Views~Sunset Deck~Grill~WIFI~Near Beaches
Exterior detail
Property grounds
Fully stocked with any type cookware needed to cook.
Living area
Exceptional
(101 reviews)

Sarasota Cozy & Clean, Near #1 Beach Siesta in SouthGate Neighborhood

Sarasota

8% off
AU$1,308
for 7 nights, 1 apartment
AU$187 per night
includes taxes & fees
Sarasota Cozy & Clean, Near #1 Beach Siesta in SouthGate Neighborhood
Living area
Eat your grilled catch of the day poolside in our new outdoor dining set for 8.
Stop by the local market and use our well-equipped kitchen for dining in.
It's cocktail hour!
Exceptional
(120 reviews)

Sunset Landing AMI Beach House. 6BR/4.5BA. Private pool. 2 blks to beach.

Holmes Beach

8% off
AU$7,426
for 7 nights, 1 home
AU$1,061 per night
includes taxes & fees
Sunset Landing AMI Beach House. 6BR/4.5BA. Private pool. 2 blks to beach.
Private kitchen
Sports court
Interior
Interior
Exceptional
(45 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
AU$2,273
for 7 nights, 1 home
AU$325 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
Open kitchen with eat-at-island and drop-leaf table for additional dining.
Bookcases open to let in more sunlight from the bedroom.
Open floor plan with living-room and kitchen great room.
A great place to watch beach goers on their way to Bean Point.
Exceptional
(202 reviews)

Shell We Dance? Charming Bungalow with Fabulous Location and Private Pool!

Anna Maria

8% off
AU$5,058
for 7 nights, 1 home
AU$723 per night
includes taxes & fees
Shell We Dance? Charming Bungalow with Fabulous Location and Private Pool!
Outdoor dining
Pool
Property grounds
Fitness facility
Excellent
(155 reviews)

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

Sarasota

8% off
AU$1,178
for 7 nights, 1 room
AU$168 per night
includes taxes & fees
Right on the Waterfront Marina - Suite 117 - 7150 N Tamiami Tail, Sarasota FL
Dining
Private kitchen
Pool
Living area
Exceptional
(62 reviews)

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

Bradenton

7% off
AU$2,926
for 7 nights, 1 home
AU$418 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
AU$3,036
for 7 nights, 1 villa
AU$434 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.
Guest bedroom downstairs with a queen bed.
Exceptional
(68 reviews)

Ingram House 2

Sarasota

5% off
AU$2,915
for 7 nights, 1 home
AU$416 per night
includes taxes & fees
Ingram House 2
Private dock for residents and guests
private rooftop deck
Dining area
living room
Exceptional
(82 reviews)

Anna Maria Sunrise on the Bay, Sunsets on the beach.Luxury 3BR with Rooftop Deck

Bradenton Beach

8% off
AU$4,070
for 7 nights, 1 apartment
AU$581 per night
includes taxes & fees
Anna Maria Sunrise on the Bay, Sunsets on the beach.Luxury 3BR with Rooftop Deck
Room
Kitchen renovated Fall 2013/Spring 2014
Dining area from living area
activity area in main building
Exceptional
(107 reviews)

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

Siesta Key

6% off
AU$3,483
for 7 nights, 1 apartment
AU$498 per night
includes taxes & fees
Palm Bay Club - Bayfront Large 2/2 Condo - Reasonable Price
Living area
Interior
Beach
Interior
Exceptional
(30 reviews)

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

Siesta Key

8% off
AU$6,452
for 7 nights, 1 home
AU$922 per night
includes taxes & fees
Beach front paradise located in a Condo Building Beach front Penthouse!
Interior
Island Time! Bridge St.
Deck off MBR
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
AU$3,518
for 7 nights, 1 home
AU$503 per night
includes taxes & fees
2 BR 2 Full BA on Anna Maria Island just steps to Beach!
Interior
Interior
Private kitchen
Living area
Exceptional
(43 reviews)

3 Minute walk to beautiful AMI beach! Old Florida Charm with a Modern Flair!

Holmes Beach

7% off
AU$1,945
for 7 nights, 1 apartment
AU$278 per night
includes taxes & fees
3 Minute walk to beautiful AMI beach! Old Florida Charm with a Modern Flair!
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    Enjoy full kitchens, laundry, pools, gardens and more
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Why visit Longboat Key

  • Pristine Beaches: Enjoy sun-drenched shores perfect for relaxation and leisurely strolls.
  • Marina Charm: Discover picturesque marina views that enhance the coastal experience.
  • Family-Friendly Atmosphere: Experience a welcoming community with attractions suited for all ages.
  • Natural Beauty: Explore scenic parks and outdoor spaces that capture the island's essence.
  • Variety of Accommodations: Choose from cosy apartments to spacious holiday homes for a comfortable stay.

Popular types of accommodation in Longboat Key

Longboat Key offers a blend of natural beauty and tranquil luxury. Enjoy pristine beaches, scenic parks and charming local attractions. Whether you’re seeking a cosy condo, a spacious private holiday home or a comfortable apartment, Longboat Key holiday rentals cater to every taste. Discover the ease and comfort of longboat key rentals, longboat key holiday rentals, longboat key rentals by owner, and holiday homes, all designed to ensure a memorable stay in this enchanting Floridian retreat.

  • Condos: The most sought-after option for holiday stays in Longboat Key, offering convenient amenities and a home-like atmosphere.
  • Private Holiday Homes: Ideal for families or groups, these homes provide a spacious environment and privacy during your getaway.
  • Apartments: A practical choice for those seeking a comfortable base, often featuring essential facilities for a relaxing stay.
  • Cottages: Quaint and charming, these smaller accommodations offer a cosy retreat amidst the beautiful surroundings.
  • Villas: Luxurious and spacious, villas provide an upscale experience with ample room for relaxation and entertainment.**

Top attractions near Longboat Key

Longboat Key offers a delightful blend of beach charm and urban park experiences, ideal for families and city enthusiasts alike. Enjoy the coastal allure and cultural attractions that this charming city has to offer, with its picturesque marina and sun-drenched beaches providing a perfect backdrop for outdoor adventures and memorable holiday experiences.

  • Lido Beach: Experience a relaxed coastal retreat with sandy shores and gentle waves, perfect for sunbathing and seaside strolls. It is located 14km away from Longboat Key.
  • St. Armands Circle: Enjoy a vibrant city atmosphere with boutique shopping and lively cafés, situated 13km from Longboat Key.
  • Longboat Key Beaches: Discover a charming neighbourhood offering scenic beaches and a blend of local culture, located 5km away from Longboat Key.

Things to do recommended for couples

Explore Longboat Key with your loved one, indulging in serene beach walks and intimate sunset cruises. Revel in local seafood and cosy nights at charming bistros for a truly memorable couple's retreat.

Things to do recommended for families

Families will love the serene beaches of Longboat Key, perfect for building sandcastles and splashing in the waves. Explore the nearby nature trails or enjoy a family picnic at the local parks, offering a delightful blend of relaxation and adventure for all ages.

Things to do recommended for groups

Groups visiting Longboat Key can enjoy local seafood feasts, bike rides along scenic coastal paths, and boat tours to spot dolphins amid the serene gulf waters.

*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

When planning your trip—be it with a group, family, pets, or for an extended stay—it's essential to refine your search according to your specific needs. Here are some helpful booking tips for Stayz.

  • Traveling to Longboat Key with a group: Think about the number of bedrooms required, along with amenities like a fully equipped kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for these features and many others on Stayz.
  • Traveling to Longboat Key with young kids: Travelling with young children can present its challenges. It's essential to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Longboat Key: For many, a family holiday wouldn’t be the same without their furry companion by their side. If this resonates with you, take a look at Stayz properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds to ensure that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Longboat Key: If you're in search of holiday rentals with discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay near Longboat Key

Longboat Key offers a delightful blend of beachside relaxation and family-friendly city experiences. Enjoy pristine shores, charming local attractions, and a warm, welcoming community. Wander through scenic spots and discover the island’s natural beauty, perfect for a leisurely holiday. Experience the essence of Longboat Key, Florida, where every moment feels like a gentle escape from the everyday hustle.

  • Sarasota: Situated 14km from Longboat Key, Sarasota is a vibrant city offering an engaging mix of urban and coastal experiences. Visitors enjoy the city's blend of beachside attractions and family-friendly urban settings, including ample shopping centres and recreational areas. The local landmarks, featuring charming town neighbourhoods and expansive family beaches, provide a glimpse into the area's rich cultural tapestry and relaxed coastal vibe.
  • Anna Maria Island: Located 11km from Longboat Key, Anna Maria Island is a naturally captivating island retreat. This destination is celebrated for its pristine beaches and outdoor activities, making it ideal for family excursions and leisurely explorations. The island's scenic cape and recreational areas complement its assortment of shopping centres and easy access to coastal delights, ensuring a refreshing escape into nature.
  • Bradenton Beach: Only 8km from Longboat Key, Bradenton Beach presents a delightful coastal city experience. With a focus on beachside relaxation and outdoor activities, this locale offers family-friendly attractions and a variety of shopping and recreational venues. The familiar town neighbourhoods and sweeping family beaches enhance the destination's appeal, crafting a balanced outing of urban convenience and natural beauty.

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. Peak season runs in March to April and July, while off-peak times, like October to December tend to have fewer bookings and better deals.

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

Booking with Stayz is a breeze

Are you hoping to save on your next holiday? Being flexible with your travel dates can be beneficial, as prices can vary. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Stayz property that fits your budget, utilise our filters to organise options by price, location, and type of holiday rental.

Stayz Trips: Effortless planning

Stayz's forward-thinking Trip Board offers you a dedicated space to craft new journeys, pick up where you last left off, or review and organise your travel plans. Properties you have previously saved or booked are now neatly categorised under Potential, Upcoming, or Current Trips. To access Trip Boards, please visit: https://www.stayz.com.au/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, Stayz 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 Stayz 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 Stayz 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, Stayz 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 Stayz.
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 Stayz.
How old do you have to be to rent a holiday home in Longboat Key?
The age limit can vary across properties on Stayz, 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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