Longboat Key holiday rentals

We found 11,778 holiday rentals — enter your dates for availability
Discover a selection of 21 homes, 19 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:4 Dec - 11 Dec

Outdoor dining
Pool
Exterior
Living area
Exceptional
(137 reviews)

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

Bradenton

8% off
S$10,224
for 7 nights, 1 home
S$1,461 per night
includes taxes & fees
6 Bedrooms - Waterfront,pool, dock, great for families. Big yard, lots of room.
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
S$3,435
for 7 nights, 1 villa
S$491 per night
includes taxes & fees
Villa & Garden in Downtown Sarasota ~ Walkable to downtown, 5 Minutes to Beaches
Private kitchen
Terrace/patio
Bathroom
Bedroom #2- Queen mattress
Exceptional
(20 reviews)

Charming 2-bedroom house in the heart of Sarasota—A quaint nature escape

Sarasota

8% off
S$1,551
for 7 nights, 1 home
S$222 per night
includes taxes & fees
Charming 2-bedroom house in the heart of Sarasota—A quaint nature escape
Exterior
Pool
Dining
Private kitchen
Exceptional
(39 reviews)

6 BR/5.5 Bth-Huge Heated Pool/Spa/Water Slide...Short -1 Min Walk to Beach

Holmes Beach

27% off
S$10,012
for 7 nights, 1 home
S$1,430 per night
includes taxes & fees
6 BR/5.5 Bth-Huge Heated Pool/Spa/Water Slide...Short -1 Min Walk to Beach
Exterior
BACKYARD OASIS WITH PRIVATE POOL
3RD LEVEL IS WHERE THE HOME IS LOCATED
BEDROOM #3 WITH KING SIZE BED & OWN BATHROOM AND SMART TV
Exceptional
(52 reviews)

NO Bunks-King beds, Garage Parking, Private Beach Access-Less Crowded

Siesta Key

8% off
S$9,046
for 7 nights, 1 home
S$1,292 per night
includes taxes & fees
NO Bunks-King beds, Garage Parking, Private Beach Access-Less Crowded
fenced in backyard
Terrace/patio
Private kitchen
Living area
Exceptional
(324 reviews)

Charming cottage in quiet area, close to beach & bay.

Anna Maria

8% off
S$3,275
for 7 nights, 1 cottage
S$468 per night
includes taxes & fees
Charming cottage in quiet area, close to beach & bay.
Aerial view with Gulf of Mexico in the backround.
Quiet Beaches.
Pool
Living room
Exceptional
(280 reviews)

Beach Access, heated pool, and new spa. Pickleball and playground along the bay!

Bradenton Beach

7% off
S$4,626
for 7 nights, 1 home
S$661 per night
includes taxes & fees
Beach Access, heated pool, and new spa. Pickleball and playground along the bay!
2nd Floor Master w/Sliding door out to 2nd story Balcony
Resort Styled 5-bdrm waterfront w/Pool/Spa/FirePit/Putting Grn/Boat/Jet Ski Lift
Terrace/patio
Dinning Room Table that Seats 10!
Wonderful
(15 reviews)

Waterfront 5BR Luxury Home – Pool, Spa, Boat Lift, Putting Green, Fire Pit

Bradenton

8% off
S$7,571
for 7 nights, 1 home
S$1,082 per night
includes taxes & fees
Waterfront 5BR Luxury Home – Pool, Spa, Boat Lift, Putting Green, Fire Pit
Terrace/patio
Sports court
Private kitchen
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
S$2,138
for 7 nights, 1 home
S$305 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
Property grounds
Dining
Property grounds
Exceptional
(12 reviews)

Canalfront Siesta key entire King suite

Siesta Key

8% off
S$2,446
for 7 nights, 1 apartment
S$349 per night
includes taxes & fees
Canalfront Siesta key entire King suite
sliding door in kitchen leads to patio area
additional bar area seating
Pool
Outdoor fire pit. Please note guests are responsible for refilling propane
Exceptional
(129 reviews)

HEATED pool, bike to Siesta, quiet street, 1 MILE to SK beach, kayaks & bikes

Sarasota

5% off
S$3,683
for 7 nights, 1 home
S$526 per night
includes taxes & fees
HEATED pool, bike to Siesta, quiet street, 1 MILE to SK beach, kayaks & bikes
Exterior
private rooftop deck
living room
Private dock for residents and guests
Exceptional
(82 reviews)

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

Bradenton Beach

7% off
S$3,638
for 7 nights, 1 apartment
S$520 per night
includes taxes & fees
Anna Maria Sunrise on the Bay, Sunsets on the beach.Luxury 3BR with Rooftop Deck
Dining
Beach
Property grounds
Exterior
Wonderful
(16 reviews)

Luxury Waterfront Views / Pool / 1400sf / Minutes to Beach

Siesta Key

8% off
S$3,791
for 7 nights, 1 apartment
S$542 per night
includes taxes & fees
Luxury Waterfront Views / Pool / 1400sf / Minutes to Beach
King bedroom
Screened porch
BBQ and Outdoor patio space
Fully stocked kitchen
Exceptional
(44 reviews)

Island House Resort - Waterfront 2-bedroom condo directly on Siesta Key Beach!

Siesta Key

6% off
S$3,578
for 7 nights, 1 room
S$511 per night
includes taxes & fees
Island House Resort - Waterfront 2-bedroom condo directly on Siesta Key Beach!
Completely renovated kitchen with all new appliances.
Come play golf on several luxurious courses in the Sarasota/Bradenton area.
Living area
Living area
Exceptional
(124 reviews)

Spacious Lakeview Condo Near IMG & Anna Maria Beaches w/ Resort Pools & Hot Tubs

Bradenton

7% off
S$1,959
for 7 nights, 1 apartment
S$280 per night
includes taxes & fees
Spacious Lakeview Condo Near IMG & Anna Maria Beaches w/ Resort Pools & Hot Tubs
Private kitchen
Marina
Property grounds
Living area
Exceptional
(38 reviews)

Siesta Key Beachside Condo-direct beach access

Siesta Key

8% off
S$3,553
for 7 nights, 1 apartment
S$508 per night
includes taxes & fees
Siesta Key Beachside Condo-direct beach access
Terrace/patio
Pool
Exterior
Property grounds
Exceptional
(17 reviews)

New The BLUE HERON 3 bedroom oasis with heated pool

Bradenton

7% off
S$2,427
for 7 nights, 1 home
S$347 per night
includes taxes & fees
New The BLUE HERON 3 bedroom oasis with heated pool
  • 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

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)
  • Tampa Bay (25.2 mi / 40.6 km)
  • Longboat Key Beaches (2.8 mi / 4.6 km)
  • Coquina Beach (3.2 mi / 5.2 km)
  • Cortez Beach (4.2 mi / 6.7 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 rental accommodation in Longboat Key?
Condos are the most popular type of holiday rental in Longboat Key, according to our data. Even if you have a different idea about what you want, Vrbo 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 rental 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 Vrbo holiday rentals 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 Vrbo and how many guests to view your rental options and prices. From there you can use our filters to narrow your search by amenities, ratings, nearby activities and more.
What are popular rental amenities in Longboat Key?
A sauna, a beach view and tennis rank as the most popular rental amenities in Longboat Key. Whether you plan to go as a party of one, with your sweetheart or as a family group, Vrbo will help you find a holiday rental 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 rentals in Longboat Key?
Longboat Key has 135 two-bedroom holiday rentals that you can choose from. Discover a holiday home with all the comfort and privacy you want at a price you'll love on Vrbo.
Are there holiday rentals with WiFi in Longboat Key?
You can pick from 94 holiday rentals 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 Vrbo.
How old do you have to be to rent a holiday rental in Longboat Key?
The age limit can vary across properties on Vrbo, so be sure to check the rules of the holiday rental in Longboat Key you want to book. But normally, it's 16, 18 or 21.
How long can I rent a holiday rental in Longboat Key for?
How long you can book a holiday rental 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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