Longboat Key holiday rentals

We found 12,059 holiday rentals — enter your dates for availability
Discover a selection of 17 homes, 15 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:8 Jan - 15 Jan

Plenty of room to host an evening in
Sundeck on rooftop with partial ocean views
Fireplace, large ceiling fan, and HDTV
Main bedroom with direct access to enclosed balcony
Exceptional
(15 reviews)

Sundeck with Ocean View, Private Access to Beach & 500ft to the Village

Siesta Key

9% off
S$5,590
for 7 nights, 1 apartment
S$799 per night
includes taxes & fees
Sundeck with Ocean View, Private Access to Beach & 500ft to the Village
Living area
Dining
Private kitchen
Interior
Exceptional
(57 reviews)

Sarasota Waterfront Paradise- Location, Location...!!

Sarasota

8% off
S$4,156
for 7 nights, 1 home
S$594 per night
includes taxes & fees
Sarasota Waterfront Paradise- Location, Location...!!
Our fully equipped kitchen that gracefully opens up to the flex space.
Open-concept kitchen/living room—ideal for socializing in style.
Open-concept living space with easy indoor-outdoor flow and patio access.
Indulge in serene relaxation at our inviting pool oasis!
Exceptional
(12 reviews)

Dog Friendly -4 Bed 2 Bath w/ HTD Pool (Sleeps 13)

Sarasota

6% off
S$5,775
for 7 nights, 1 home
S$825 per night
includes taxes & fees
Dog Friendly -4 Bed 2 Bath w/ HTD Pool (Sleeps 13)
Dining
BACKYARD OASIS WITH PRIVATE POOL
GREAT OUTDOOR SEATING AREA FOR THE WHOLE FAMILY TO ENJOY!
Living area
Exceptional
(52 reviews)

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

Siesta Key

8% off
S$10,192
for 7 nights, 1 home
S$1,456 per night
includes taxes & fees
NO Bunks-King beds, Garage Parking, Private Beach Access-Less Crowded
Gumbo tree in front yard
Quiet spot in paradise
Patio French door with keypad left of door.
French doors to the lanai and 60 inch TV on the wall.
Exceptional
(92 reviews)

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

Bradenton

8% off
S$2,138
for 7 nights, 1 home
S$305 per night
includes taxes & fees
Quiet cozy home near Anna Maria Island, Robinson Preserve, DeSoto Nt’l Monument
Private kitchen
Marina
Exterior
Living area
Exceptional
(43 reviews)

Siesta Key Beachside Condo-direct beach access

Siesta Key

8% off
S$3,550
for 7 nights, 1 apartment
S$507 per night
includes taxes & fees
Siesta Key Beachside Condo-direct beach access
Terrace/patio
Private kitchen
Exterior detail
Dining
Exceptional
(84 reviews)

Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.

Sarasota

8% off
S$2,416
for 7 nights, 1 home
S$345 per night
includes taxes & fees
Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.
Terrace/patio
Living area
Private kitchen
Room
Exceptional
(134 reviews)

Lido Beach Walk! One block to beach!

Sarasota

8% off
S$2,035
for 7 nights, 1 room
S$291 per night
includes taxes & fees
Lido Beach Walk! One block to beach!
Room
Terrace/patio
Private kitchen
Private kitchen
Exceptional
(7 reviews)

For family fun or a romantic escape close to sarasota and the area"s beaches

Bradenton

9% off
S$2,262
for 7 nights, 1 villa
S$323 per night
includes taxes & fees
For family fun or a romantic escape close to sarasota and the area"s beaches
Primary Bedroom
Gas heated saltwater spa! (free all year round)
Interior
Screened outdoor dining for eight - NO BUGS!
Exceptional
(211 reviews)

4 Bedroom, 2 Bath. Heated Pool & Spa! Close to Beaches!

Bradenton

8% off
S$3,549
for 7 nights, 1 home
S$507 per night
includes taxes & fees
4 Bedroom, 2 Bath. Heated Pool & Spa! Close to Beaches!
Interior
Living area
Terrace/patio
Entryway
Exceptional
(22 reviews)

Modern Villa steps away from the white sandy beach on upscale Lido Key, Sarasota

Sarasota

16% off
S$3,458
for 7 nights, 1 villa
S$494 per night
includes taxes & fees
Modern Villa steps away from the white sandy beach on upscale Lido Key, Sarasota
Private kitchen
Property grounds
Beach
Room
Exceptional
(38 reviews)

Perfect 1-bedroom condo with AC in Bradenton Beach

Bradenton Beach

8% off
S$3,162
for 7 nights, 1 apartment
S$452 per night
includes taxes & fees
Perfect 1-bedroom condo with AC in Bradenton Beach
Back sitting/reading area looking out to pool
Beautiful private pool - heated in the winter and cooled in the summer!
Private kitchen
Front king size bedroom with en suite
Exceptional
(106 reviews)

Steps from the beach!

Bradenton Beach

12% off
S$4,596
for 7 nights, 1 home
S$657 per night
includes taxes & fees
Steps from the beach!
Private kitchen
Terrace/patio
Bathroom
Living area
Exceptional
(22 reviews)

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

Sarasota

8% off
S$2,384
for 7 nights, 1 home
S$341 per night
includes taxes & fees
Charming 2-bedroom house in the heart of Sarasota—A quaint nature escape
Living area
Private kitchen
Terrace/patio
Room
Exceptional
(111 reviews)

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

Anna Maria

8% off
S$5,239
for 7 nights, 1 home
S$748 per night
includes taxes & fees
75 ft Canal Front Anna Maria House, Great for Boaters, Newly Renovated
Room
Living area
Private kitchen
Outdoor dining
Exceptional
(106 reviews)

Shorewalk The Palm Condo 2Bed/2Bath Close to IMG / Beach

Bradenton

6% off
S$2,246
for 7 nights, 1 apartment
S$321 per night
includes taxes & fees
Shorewalk The Palm Condo 2Bed/2Bath Close to IMG / Beach
Fitness facility
Outdoor dining
Heated waterfront pool
Marina
Very good
(164 reviews)

SARASOTA Waterfront hotel Room KING BED # 215 ON SARA BAY 7150 N Tamiami Trail

Sarasota

8% off
S$1,080
for 7 nights, 1 room
S$154 per night
includes taxes & fees
SARASOTA Waterfront hotel Room KING BED # 215 ON SARA BAY 7150 N Tamiami Trail
Dining
Private kitchen
Living area
Terrace/patio
Exceptional
(65 reviews)

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

Bradenton

8% off
S$3,437
for 7 nights, 1 home
S$491 per night
includes taxes & fees
Ila's Beach House: Near IMG-Heated Salt Pool- Pets OK-Modern Organic Smart Home
Watch the sunrise at the Bradenton Beach. Great place for a morning run or walk.
Amped Fitness is within walking distance from the condo.
Inside photo of the Shorewalk clubhouse.
Exceptional
(161 reviews)

Resort Corner Condo Near Anna Maria Island & IMG with Heated Pools & Hot Tubs

Bradenton

8% off
S$2,282
for 7 nights, 1 apartment
S$326 per night
includes taxes & fees
Resort Corner Condo Near Anna Maria Island & IMG with Heated Pools & Hot Tubs
Bathroom
Pool
Room
Beach
Exceptional
(38 reviews)

Adorable 1-bedroom condo in beautiful Bradenton Beach with AC

Bradenton Beach

8% off
S$2,620
for 7 nights, 1 apartment
S$374 per night
includes taxes & fees
Adorable 1-bedroom condo in beautiful Bradenton Beach with AC
  • 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. Lido Beach and Siesta Key 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)
  • University Park Country Club (11.2 mi / 18.1 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)

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:

  • Lido Beach (8.8 mi / 14.2 km)
  • Siesta Key Beach (12 mi / 19.4 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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