Longboat Key holiday rentals

We found 11,905 holiday rentals — enter your dates for availability
Discover a selection of 19 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:25 Dec - 1 Jan

French doors to the lanai and 60 inch TV on the wall.
Quiet spot in paradise
Have your morning coffee on the lanai.
Gumbo tree in front yard
Exceptional
(92 reviews)

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

Bradenton

8% off
S$2,186
for 7 nights, 1 home
S$312 per night
includes taxes & fees
Quiet cozy home near Anna Maria Island, Robinson Preserve, DeSoto Nt’l Monument
Manatee River with 120 ft dock
Kitchen
View of River from house
Rainbow at The Cut House
Exceptional
(64 reviews)

Snead Island Cut Home - Oceanfront near Anna Maria , Boat docking, pet friendly

Palmetto

8% off
S$4,081
for 7 nights, 1 home
S$583 per night
includes taxes & fees
Snead Island Cut Home - Oceanfront near Anna Maria , Boat docking, pet friendly
Living, lounging, cooking—our space does it all.
Anna Maria, Florida's ocean is your ultimate fun zone!
Pool
Your ideal mix of style, convenience, and comfort is ready and waiting for you.
Exceptional
(56 reviews)

Luxury Family Escape: Spacious 4BR, Pool, Close to AMI, Dining & Attractions!

Bradenton

8% off
S$10,084
for 7 nights, 1 home
S$1,441 per night
includes taxes & fees
Luxury Family Escape: Spacious 4BR, Pool, Close to AMI, Dining & Attractions!
Dining
Private kitchen
Room
Terrace/patio
Exceptional
(84 reviews)

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

Sarasota

8% off
S$2,377
for 7 nights, 1 home
S$340 per night
includes taxes & fees
Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.
Master Bedroom with natural light
Exterior detail
Living area
Dining
Exceptional
(33 reviews)

Downtown Sarasota near Lido and Siesta

Sarasota

8% off
S$2,580
for 7 nights, 1 home
S$369 per night
includes taxes & fees
Downtown Sarasota near Lido and Siesta
Room
Pool
Property grounds
Fitness facility
Excellent
(156 reviews)

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

Sarasota

8% off
S$1,077
for 7 nights, 1 room
S$154 per night
includes taxes & fees
Right on the Waterfront Marina - Suite 117 - 7150 N Tamiami Tail, Sarasota FL
Room
Pool
Bathroom
Room
Exceptional
(37 reviews)

Adorable 1-bedroom condo in beautiful Bradenton Beach with AC

Bradenton Beach

8% off
S$2,803
for 7 nights, 1 apartment
S$400 per night
includes taxes & fees
Adorable 1-bedroom condo in beautiful Bradenton Beach with AC
Fitness facility
Outdoor dining
Marina
Waterfront restaurant on premisis with live music
Very good
(164 reviews)

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

Sarasota

8% off
S$1,064
for 7 nights, 1 room
S$152 per night
includes taxes & fees
SARASOTA Waterfront hotel Room KING BED # 215 ON SARA BAY 7150 N Tamiami Trail
Interior
Room
Beach
Living area
Exceptional
(6 reviews)

Private Suite w/ Lounge & Private Patio

Bradenton

8% off
S$866
for 7 nights, 1 apartment
S$124 per night
includes taxes & fees
Private Suite w/ Lounge & Private Patio
Interior
Beach
King bed
Living area
Exceptional
(24 reviews)

Good Vibrations- Stay right ON the beach in Siesta Key! Sleeps 6

Siesta Key

8% off
S$4,663
for 7 nights, 1 apartment
S$666 per night
includes taxes & fees
Good Vibrations- Stay right ON the beach in Siesta Key! Sleeps 6
Cable tv
Unit 6 with vegetation no longer there
Salt Bar and Table
Local artist painted bar seats
Exceptional
(42 reviews)

Gulf Front • Steps to Sand • Sunset View • Balcony

Bradenton Beach

8% off
S$6,559
for 7 nights, 1 apartment
S$937 per night
includes taxes & fees
Gulf Front • Steps to Sand • Sunset View • Balcony
Dining
Private kitchen
Pool
Living area
Exceptional
(65 reviews)

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

Bradenton

8% off
S$6,847
for 7 nights, 1 home
S$978 per night
includes taxes & fees
Ila's Beach House: Near IMG-Heated Salt Pool- Pets OK-Modern Organic Smart Home
Children’s area
Terrace/patio
Interior
Interior
Exceptional
(16 reviews)

Beautiful house close to IMG, Anna Maria Island and Siesta Key.

Bradenton

6% off
S$4,024
for 7 nights, 1 home
S$575 per night
includes taxes & fees
Beautiful house close to IMG, Anna Maria Island and Siesta Key.
Living area
Terrace/patio
Bathroom
Bedroom #2- Queen mattress
Exceptional
(21 reviews)

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

Sarasota

8% off
S$2,193
for 7 nights, 1 home
S$313 per night
includes taxes & fees
Charming 2-bedroom house in the heart of Sarasota—A quaint nature escape
Exterior
Interior
Interior
Interior
Wonderful
(9 reviews)

Family Pool Home Near Anna Maria Island & IMG

Bradenton

7% off
S$2,828
for 7 nights, 1 home
S$404 per night
includes taxes & fees
Family Pool Home Near Anna Maria Island & IMG
Private kitchen
Marina
Living area
Exterior
Exceptional
(41 reviews)

Siesta Key Beachside Condo-direct beach access

Siesta Key

8% off
S$3,532
for 7 nights, 1 apartment
S$505 per night
includes taxes & fees
Siesta Key Beachside Condo-direct beach access
Interior
Room
Interior
Dining
Excellent
(25 reviews)

Centrally Located Charming Beach Suite in Sarasota

Sarasota

8% off
S$1,086
for 7 nights, 1 apartment
S$155 per night
includes taxes & fees
Centrally Located Charming Beach Suite in Sarasota
Room
Private kitchen
Interior
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$2,193
for 7 nights, 1 home
S$313 per night
includes taxes & fees
Renovated 2-bed 2 bath home with Pool, Garage, just a bike ride to Siesta Key!
Tiki bar and pool
Rental Boats and Tiki Bar
Interior
Pool and Tiki Bar
Exceptional
(16 reviews)

Waterfront Executive Studio Pool Marina and Bay Views Labor Day Weekend Special

Sarasota

8% off
S$2,212
for 7 nights, 1 apartment
S$316 per night
includes taxes & fees
Waterfront Executive Studio Pool Marina and Bay Views Labor Day Weekend Special
Pool
Outdoor dining
Fitness facility
Marina
Very good
(175 reviews)

Sarasota “Deluxe King Waterfront Suite” #201 At the Hotel at 7150 N TAMIAMI TR

Sarasota

8% off
S$977
for 7 nights, 1 room
S$140 per night
includes taxes & fees
Sarasota “Deluxe King Waterfront Suite” #201 At the Hotel at 7150 N TAMIAMI TR
Private kitchen
Interior
Interior
Room
Exceptional
(27 reviews)

Family Poolside Paradise on Quiet Cul-de-Sac 4.7 Miles from Siesta Key Beach

Sarasota

8% off
S$5,928
for 7 nights, 1 home
S$847 per night
includes taxes & fees
Family Poolside Paradise on Quiet Cul-de-Sac 4.7 Miles from Siesta Key Beach
Pool
Enclosed patio area with private pool
Interior
Dining table + 2 barstools for extra seating
Exceptional
(57 reviews)

Serene yard and pool, 1 mile to beach, pets OK, patio TV, Kayaks

Sarasota

5% off
S$4,387
for 7 nights, 1 home
S$627 per night
includes taxes & fees
Serene yard and pool, 1 mile to beach, pets OK, patio TV, Kayaks
Private kitchen
Private rear patio
Entry shelves with extra beach towels, cooler, futon blankets, etc
Living Room, makeup vanity or desk, and kitchen
Exceptional
(21 reviews)

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

Siesta Key

8% off
S$3,487
for 7 nights, 1 apartment
S$498 per night
includes taxes & fees
Siesta Key Beach Cottage-Prime Location! Walkable. Luxury Amenities & Comfort!
Interior
Terrace/patio
Interior
Dining
Exceptional
(13 reviews)

Gracie's Cottage 15 min to Beach

Bradenton

8% off
S$3,168
for 7 nights, 1 home
S$453 per night
includes taxes & fees
Gracie's Cottage 15 min to 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.

More holiday ideas