Longboat Key holiday rentals

We found 12,148 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:15 Jan - 22 Jan

75" TV perfect for movie nights.
Sophisticated and serene Mediterranean beach home.
Private, heated pool and spa with canal views and your own private dock.
Large dining room opens to living area, offering seamless entertaining space.
Exceptional
(14 reviews)

Casa del Siesta— Mediterranean Luxury by the Beach with Pool, Spa & Private Dock

Siesta Key

7% off
S$9,490
for 7 nights, 1 home
S$1,356 per night
includes taxes & fees
Casa del Siesta— Mediterranean Luxury by the Beach with Pool, Spa & Private Dock
Indulge in serene relaxation at our inviting pool oasis!
Open-concept kitchen/living room—ideal for socializing in style.
Elegant dining room seats six, ideal for family meals.
Our fully equipped kitchen that gracefully opens up to the flex space.
Exceptional
(12 reviews)

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

Sarasota

6% off
S$6,078
for 7 nights, 1 home
S$868 per night
includes taxes & fees
Dog Friendly -4 Bed 2 Bath w/ HTD Pool (Sleeps 13)
Pool
additional bar area seating
Front (living) room
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$4,044
for 7 nights, 1 home
S$578 per night
includes taxes & fees
HEATED pool, bike to Siesta, quiet street, 1 MILE to SK beach, kayaks & bikes
Living area
Interior
Living area
Dining
Exceptional
(20 reviews)

5BR with New Heated Pool ! 6mi from AMI Beach & IMG Academy! Spring Break Sales

Bradenton

11% off
S$4,705
for 7 nights, 1 home
S$672 per night
includes taxes & fees
5BR with New Heated Pool ! 6mi from AMI Beach & IMG Academy! Spring Break Sales
Living area
Private kitchen
Interior
Exterior detail
Exceptional
(34 reviews)

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

Sarasota

8% off
S$2,744
for 7 nights, 1 home
S$392 per night
includes taxes & fees
Renovated 2-bed 2 bath home with Pool, Garage, just a bike ride to Siesta Key!
Room
Private kitchen
Exterior detail
Terrace/patio
Exceptional
(84 reviews)

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

Sarasota

8% off
S$2,419
for 7 nights, 1 home
S$346 per night
includes taxes & fees
Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.
Exterior
Resort Styled 5-bdrm waterfront w/Pool/Spa/FirePit/Putting Grn/Boat/Jet Ski Lift
2nd Floor Master w/Sliding door out to 2nd story Balcony
Dinning Room Table that Seats 10!
Wonderful
(17 reviews)

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

Bradenton

8% off
S$8,113
for 7 nights, 1 home
S$1,159 per night
includes taxes & fees
Waterfront 5BR Luxury Home – Pool, Spa, Boat Lift, Putting Green, Fire Pit
Enjoy a great night sleep on this king size bed in the master bedroom.
Living area
Aerial photo of Shorewalk. Great view of the clubhouse, pools and tennis courts.
Beach
Exceptional
(126 reviews)

Lake-view Corner Condo Near Anna Maria Island & IMG with Heated Pools & Hot Tubs

Bradenton

8% off
S$2,308
for 7 nights, 1 apartment
S$330 per night
includes taxes & fees
Lake-view Corner Condo Near Anna Maria Island & IMG with Heated Pools & Hot Tubs
Glassed in and screened porch
Sports court
Exterior
Terrace/patio
Exceptional
(185 reviews)

Amazing 1 Br/1 Ba Condo at Casa Mar

Siesta Key

7% off
S$2,987
for 7 nights, 1 apartment
S$427 per night
includes taxes & fees
Amazing 1 Br/1 Ba Condo at Casa Mar
Room
Pool
Beach
Bathroom
Exceptional
(38 reviews)

Adorable 1-bedroom condo in beautiful Bradenton Beach with AC

Bradenton Beach

8% off
S$2,623
for 7 nights, 1 apartment
S$375 per night
includes taxes & fees
Adorable 1-bedroom condo in beautiful Bradenton Beach with AC
Property grounds
Pool
Fitness facility
Outdoor dining
Excellent
(156 reviews)

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

Sarasota

8% off
S$1,094
for 7 nights, 1 room
S$156 per night
includes taxes & fees
Right on the Waterfront Marina - Suite 117 - 7150 N Tamiami Tail, Sarasota FL
spare bedding & pillows for the futon is in the closet.
Living area / king size bed with balcony, overlooking the beach.
Condo pool with tables and chairs and large shaded seating area!
Dining table looking into kitchenette, fridge, microwave, two burner stove.
Exceptional
(8 reviews)

The Pelican's Perch, a Beachfront studio condo w/ balcony

Bradenton Beach

8% off
S$2,871
for 7 nights, 1 apartment
S$410 per night
includes taxes & fees
The Pelican's Perch, a Beachfront studio condo w/ balcony
Bedroom #2- Queen mattress
Terrace/patio
Bathroom
Living area
Exceptional
(22 reviews)

Charming Cottage in the heart of Sarasota—A quaint nature escape

Sarasota

8% off
S$2,407
for 7 nights, 1 home
S$344 per night
includes taxes & fees
Charming Cottage in the heart of Sarasota—A quaint nature escape
Living area
Private kitchen
Terrace/patio
Dining
Exceptional
(66 reviews)

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

Bradenton

8% off
S$4,116
for 7 nights, 1 home
S$588 per night
includes taxes & fees
Ila's Beach House: Near IMG-Heated Salt Pool- Pets OK-Modern Organic Smart Home
Waterfront restaurant on premisis with live music
Outdoor dining
Marina
Heated waterfront pool
Very good
(164 reviews)

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

Sarasota

8% off
S$1,082
for 7 nights, 1 room
S$155 per night
includes taxes & fees
SARASOTA Waterfront hotel Room KING BED # 215 ON SARA BAY 7150 N Tamiami Trail
Dining
Private kitchen
Pool
Interior
Exceptional
(62 reviews)

Newly Renovated Family Vacation Rental with Pool & Spa

Bradenton

8% off
S$2,399
for 7 nights, 1 home
S$343 per night
includes taxes & fees
Newly Renovated Family Vacation Rental with Pool & Spa
Exterior
Beach
Outdoor dining
Room
Exceptional
(106 reviews)

Low Rider - Bottom Unit -

Bradenton Beach

8% off
S$4,391
for 7 nights, 1 home
S$627 per night
includes taxes & fees
Low Rider - Bottom Unit -
Inside photo of the Shorewalk clubhouse.
Watch the sunrise at the Bradenton Beach. Great place for a morning run or walk.
Come play golf on several luxurious courses in the Sarasota/Bradenton area.
Amped Fitness is within walking distance from the condo.
Exceptional
(161 reviews)

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

Bradenton

8% off
S$2,293
for 7 nights, 1 apartment
S$328 per night
includes taxes & fees
Resort Corner Condo Near Anna Maria Island & IMG with Heated Pools & Hot Tubs
Beach
Property grounds
Pool
Private kitchen
Exceptional
(38 reviews)

Perfect 1-bedroom condo with AC in Bradenton Beach

Bradenton Beach

8% off
S$3,165
for 7 nights, 1 apartment
S$452 per night
includes taxes & fees
Perfect 1-bedroom condo with AC in Bradenton Beach
  • 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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