Longboat Key holiday rentals

We found 12,144 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

Dining
Dining
Private kitchen
Living area
Exceptional
(57 reviews)

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

Sarasota

8% off
S$4,159
for 7 nights, 1 home
S$594 per night
includes taxes & fees
Sarasota Waterfront Paradise- Location, Location...!!
Room
Interior
Interior
Private kitchen
Exceptional
(45 reviews)

KEY DREAMS-LARGE HEATED POOL-3 BR-10 MIN TO SIESTA KEY-SLEEPS 8-GULF GATE

Sarasota

8% off
S$3,834
for 7 nights, 1 home
S$548 per night
includes taxes & fees
KEY DREAMS-LARGE HEATED POOL-3 BR-10 MIN TO SIESTA KEY-SLEEPS 8-GULF GATE
Living area
Property grounds
Living area
Private kitchen
Exceptional
(43 reviews)

Siesta Key Beachside Condo-direct beach access

Siesta Key

8% off
S$3,558
for 7 nights, 1 apartment
S$508 per night
includes taxes & fees
Siesta Key Beachside Condo-direct beach access
Room
Private kitchen
Exterior detail
Living area
Exceptional
(34 reviews)

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

Sarasota

8% off
S$2,743
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!
Private kitchen
Living area
Room
Interior
Exceptional
(134 reviews)

Lido Beach Walk! One block to beach!

Sarasota

8% off
S$2,036
for 7 nights, 1 room
S$291 per night
includes taxes & fees
Lido Beach Walk! One block to beach!
Champagne spa heats up to 101--you won't want to leave it!
Breathtaking upstairs master with 270 degree views; rooftop deck off the master
Fully stocked kitchen has everything you will need; soap provided
Room
Exceptional
(43 reviews)

Private POOL/SPA-Almost beachfront, Amazing Gulf Views, walk to Bridge St.

Bradenton Beach

7% off
S$8,808
for 7 nights, 1 home
S$1,258 per night
includes taxes & fees
Private POOL/SPA-Almost beachfront, Amazing Gulf Views, walk to Bridge St.
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$2,391
for 7 nights, 1 apartment
S$342 per night
includes taxes & fees
Lake-view Corner Condo Near Anna Maria Island & IMG with Heated Pools & Hot Tubs
Private kitchen
Property grounds
Beach
Room
Exceptional
(38 reviews)

Perfect 1-bedroom condo with AC in Bradenton Beach

Bradenton Beach

8% off
S$3,164
for 7 nights, 1 apartment
S$452 per night
includes taxes & fees
Perfect 1-bedroom condo with AC in Bradenton Beach
Fitness facility
Pool
Room
Property grounds
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
Living Room, makeup vanity or desk, and kitchen
Private rear patio
New Queen Bed with plenty of pillows to choose to your liking.
Private kitchen
Exceptional
(22 reviews)

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

Siesta Key

8% off
S$3,759
for 7 nights, 1 apartment
S$537 per night
includes taxes & fees
Siesta Key Beach Cottage-Prime Location! Walkable. Luxury Amenities & Comfort!
Private kitchen
Terrace/patio
Bedroom #2- Queen mattress
Bathroom
Exceptional
(22 reviews)

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

Sarasota

8% off
S$2,406
for 7 nights, 1 home
S$344 per night
includes taxes & fees
Charming Cottage in the heart of Sarasota—A quaint nature escape
Exterior
Beach
Interior
Front: Kids park, pickleball, basketball, and access intercoastal 2 blocks.
Exceptional
(313 reviews)

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

Bradenton Beach

11% off
S$6,146
for 7 nights, 1 home
S$878 per night
includes taxes & fees
Beach Access, heated pool, and new spa. Pickleball and playground along the bay!
Room
Living area
Outdoor dining
Private kitchen
Exceptional
(106 reviews)

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

Bradenton

6% off
S$2,247
for 7 nights, 1 apartment
S$321 per night
includes taxes & fees
Shorewalk The Palm Condo 2Bed/2Bath Close to IMG / Beach
Marina
Private kitchen
Room
Living area
Exceptional
(111 reviews)

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

Anna Maria

8% off
S$5,243
for 7 nights, 1 home
S$749 per night
includes taxes & fees
75 ft Canal Front Anna Maria House, Great for Boaters, Newly Renovated
Pool
Private kitchen
Living area
Dining
Exceptional
(66 reviews)

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

Bradenton

8% off
S$4,148
for 7 nights, 1 home
S$593 per night
includes taxes & fees
Ila's Beach House: Near IMG-Heated Salt Pool- Pets OK-Modern Organic Smart Home
Patio tables by heated pool.
View from ocean towards our community.
Heated Pool is right outside condo entrance.
Patio tables by heated pool.
Exceptional
(68 reviews)

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

Siesta Key

9% off
S$2,372
for 7 nights, 1 apartment
S$339 per night
includes taxes & fees
Steps to Siesta Key BEACH! Pool, Tennis Court, Shuffle Board, Pickle Ball!
Private kitchen
Beach
Exterior
Room
Exceptional
(106 reviews)

Low Rider - Bottom Unit -

Bradenton Beach

8% off
S$4,389
for 7 nights, 1 home
S$627 per night
includes taxes & fees
Low Rider - Bottom Unit -
  • 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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