Longboat Key holiday rentals

We found 12,230 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:22 Jan - 29 Jan

Picture #1
Exceptional
(83 reviews)

Jamaica Royale | 3 Pools, Beach & Free Activities

Siesta Key

7% off
S$4,041
for 7 nights, 1 apartment
S$577 per night
includes taxes & fees
Jamaica Royale | 3 Pools, Beach & Free Activities
Dining table right off the kitchen.
Exceptional
(149 reviews)

Lulu’s Loggerhead, Heated Pool, Walk to Village

Siesta Key

7% off
S$4,286
for 7 nights, 1 apartment
S$612 per night
includes taxes & fees
Lulu’s Loggerhead, Heated Pool, Walk to Village
BACKYARD OASIS WITH PRIVATE POOL
Exceptional
(52 reviews)

Siesta Coastal Oasis - 5 Min Paved Walk to the Private Beach

Siesta Key

8% off
S$12,700
for 7 nights, 1 home
S$1,814 per night
includes taxes & fees
Siesta Coastal Oasis - 5 Min Paved Walk to the Private Beach
Private kitchen
Excellent
(18 reviews)

Heated Pool | Hot Tub | Waterfront Views | IMG

Bradenton

25% off
S$5,096
for 7 nights, 1 home
S$728 per night
includes taxes & fees
Heated Pool | Hot Tub | Waterfront Views | IMG
additional bar area seating
Exceptional
(129 reviews)

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

Sarasota

5% off
S$3,830
for 7 nights, 1 home
S$547 per night
includes taxes & fees
HEATED pool, bike to Siesta, quiet street, 1 MILE to SK beach, kayaks & bikes
Enjoy evenings on Siesta with a dip in the heated pool
Exceptional
(62 reviews)

Walk to Beach + Village, Beach Gear Included, Pool

Siesta Key

7% off
S$3,992
for 7 nights, 1 apartment
S$570 per night
includes taxes & fees
Walk to Beach + Village, Beach Gear Included, Pool
Living area
Exceptional
(46 reviews)

Location Location! Two Minutes from Siesta Key Beach (#1 Beach in the U.S.)

Sarasota

7% off
S$2,291
for 7 nights, 1 home
S$327 per night
includes taxes & fees
Location Location! Two Minutes from Siesta Key Beach (#1 Beach in the U.S.)
Bay Front Sunrise View (Patio)
Exceptional
(84 reviews)

Bayfront 2025 Reno - 2 King Suites - Pool - Boat Dock - Walk to Beach & Pier

Bradenton Beach

8% off
S$5,268
for 7 nights, 1 apartment
S$753 per night
includes taxes & fees
Bayfront 2025 Reno - 2 King Suites - Pool - Boat Dock - Walk to Beach & Pier
Living area
Exceptional
(44 reviews)

Siesta Key Beachside Condo-direct beach access

Siesta Key

8% off
S$3,546
for 7 nights, 1 apartment
S$507 per night
includes taxes & fees
Siesta Key Beachside Condo-direct beach access
Private kitchen
Exceptional
(35 reviews)

Renovated 2-bed 2 bath home with Pool, Garage, just a bike ride to Siesta Key!

Sarasota

8% off
S$2,732
for 7 nights, 1 home
S$390 per night
includes taxes & fees
Renovated 2-bed 2 bath home with Pool, Garage, just a bike ride to Siesta Key!
Picture #1
Wonderful
(65 reviews)

2-Story Townhome: Steps from the Sand & Gulf Views

Siesta Key

7% off
S$4,855
for 7 nights, 1 apartment
S$694 per night
includes taxes & fees
2-Story Townhome: Steps from the Sand & Gulf Views
Living area
Exceptional
(135 reviews)

Lido Beach Walk! One block to beach!

Sarasota

8% off
S$2,032
for 7 nights, 1 room
S$290 per night
includes taxes & fees
Lido Beach Walk! One block to beach!
Terrace/patio
Exceptional
(8 reviews)

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

Bradenton

9% off
S$2,151
for 7 nights, 1 villa
S$307 per night
includes taxes & fees
For family fun or a romantic escape close to sarasota and the area"s beaches
Resort Styled 5-bdrm waterfront w/Pool/Spa/FirePit/Putting Grn/Boat/Jet Ski Lift
Wonderful
(17 reviews)

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

Bradenton

8% off
S$8,590
for 7 nights, 1 home
S$1,227 per night
includes taxes & fees
Waterfront 5BR Luxury Home – Pool, Spa, Boat Lift, Putting Green, Fire Pit
Your private pool at dusk, lit beside the hand-painted tropical murals. Pool heat is included, so winter swims after an IMG Academy game or a beach day happen right in your fenced backyard.
Exceptional
(16 reviews)

⭐ Heated pool near IMG, putting green + arcade

Bradenton

11% off
S$3,257
for 7 nights, 1 home
S$465 per night
includes taxes & fees
⭐ Heated pool near IMG, putting green + arcade
Room
Exceptional
(39 reviews)

Adorable 1-bedroom condo in beautiful Bradenton Beach with AC

Bradenton Beach

8% off
S$2,615
for 7 nights, 1 apartment
S$374 per night
includes taxes & fees
Adorable 1-bedroom condo in beautiful Bradenton Beach with AC
Private kitchen
Exceptional
(111 reviews)

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

Anna Maria

8% off
S$5,398
for 7 nights, 1 home
S$771 per night
includes taxes & fees
75 ft Canal Front Anna Maria House, Great for Boaters, Newly Renovated
A "close-up" view from the balcony.....
Exceptional
(104 reviews)

Siesta Sands Private Beach | Gulf Views | Htd Pool

Siesta Key

7% off
S$6,131
for 7 nights, 1 apartment
S$876 per night
includes taxes & fees
Siesta Sands Private Beach | Gulf Views | Htd Pool
Quiet and safe neighborhood for families to swim, walk, bike, and fish
Exceptional
(102 reviews)

Gulf & Bay Club Bayside, 1st Floor, CLEAN, 5 STARS & EXCELLENT REVIEWS!

Siesta Key

5% off
S$4,957
for 7 nights, 1 apartment
S$708 per night
includes taxes & fees
Gulf & Bay Club Bayside, 1st Floor, CLEAN, 5 STARS & EXCELLENT REVIEWS!
Private rear patio
Exceptional
(22 reviews)

Siesta Key Beach Cottage-Prime Location! Walkable. Luxury Amenities & Comfort!

Siesta Key

17% off
S$3,262
for 7 nights, 1 apartment
S$466 per night
includes taxes & fees
Siesta Key Beach Cottage-Prime Location! Walkable. Luxury Amenities & Comfort!
View from ocean towards our community.
Exceptional
(68 reviews)

Steps to Siesta Key BEACH! Pool, Tennis Court, Shuffle Board, Pickle Ball!

Siesta Key

9% off
S$2,363
for 7 nights, 1 apartment
S$338 per night
includes taxes & fees
Steps to Siesta Key BEACH! Pool, Tennis Court, Shuffle Board, Pickle Ball!
Property grounds
Very good
(164 reviews)

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

Sarasota

8% off
S$1,078
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
Private kitchen
Exceptional
(62 reviews)

Newly Renovated Family Vacation Rental with Pool & Spa

Bradenton

8% off
S$2,392
for 7 nights, 1 home
S$342 per night
includes taxes & fees
Newly Renovated Family Vacation Rental with Pool & Spa
Heated dipping pool with an outdoor shower is shared with the other cottage.
Exceptional
(23 reviews)

Relax at Lulu's! Pool, Walk to Beach, Dog friendly

Siesta Key

7% off
S$4,739
for 7 nights, 1 apartment
S$677 per night
includes taxes & fees
Relax at Lulu's! Pool, Walk to Beach, Dog friendly
  • 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.

More holiday ideas