Longboat Key holiday rentals

We found 12,224 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:29 Jan - 5 Feb

Picture #1
Exceptional
(83 reviews)

Jamaica Royale | 3 Pools, Beach & Free Activities

Siesta Key

7% off
S$4,571
for 7 nights, 1 apartment
S$653 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$4,818
for 7 nights, 1 apartment
S$688 per night
includes taxes & fees
Lulu’s Loggerhead, Heated Pool, Walk to Village
Interior
Exceptional
(45 reviews)

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

Sarasota

8% off
S$4,082
for 7 nights, 1 home
S$583 per night
includes taxes & fees
KEY DREAMS-LARGE HEATED POOL-3 BR-10 MIN TO SIESTA KEY-SLEEPS 8-GULF GATE
Private kitchen
Excellent
(18 reviews)

Heated Pool | Hot Tub | Waterfront Views | IMG

Bradenton

25% off
S$5,916
for 7 nights, 1 home
S$845 per night
includes taxes & fees
Heated Pool | Hot Tub | Waterfront Views | IMG
Enjoy your morning coffee and cereal in the backyard with singing Seaside Sparrows....
Exceptional
(47 reviews)

Perfect Location, Dog Friendly, Mins to Siesta Key

Sarasota

7% off
S$3,735
for 7 nights, 1 home
S$534 per night
includes taxes & fees
Perfect Location, Dog Friendly, Mins to Siesta Key
BACKYARD OASIS WITH PRIVATE POOL
Exceptional
(52 reviews)

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

Siesta Key

8% off
S$14,298
for 7 nights, 1 home
S$2,043 per night
includes taxes & fees
Siesta Coastal Oasis - 5 Min Paved Walk to the Private Beach
Kitchen
Exceptional
(65 reviews)

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

Palmetto

8% off
S$3,872
for 7 nights, 1 home
S$553 per night
includes taxes & fees
Snead Island Cut Home - Oceanfront near Anna Maria , Boat docking, pet friendly
Exterior
Exceptional
(5 reviews)

Coastal Canopy, Private Pool: 15 Min to Beach

Bradenton

8% off
S$2,964
for 7 nights, 1 home
S$423 per night
includes taxes & fees
Coastal Canopy, Private Pool: 15 Min to Beach
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$5,035
for 7 nights, 1 apartment
S$719 per night
includes taxes & fees
Walk to Beach + Village, Beach Gear Included, Pool
Large living area with million dollar views of the Gulf of Mexico!
Excellent
(13 reviews)

Ocean Views! Across from Siesta Beach, Heated Pool

Siesta Key

7% off
S$5,600
for 7 nights, 1 apartment
S$800 per night
includes taxes & fees
Ocean Views! Across from Siesta Beach, Heated Pool
Interior
Exceptional
(20 reviews)

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

Bradenton

12% off
S$5,200
for 7 nights, 1 home
S$743 per night
includes taxes & fees
5BR with New Heated Pool ! 6mi from AMI Beach & IMG Academy! Spring Break Sales
Picture #1
Wonderful
(65 reviews)

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

Siesta Key

7% off
S$5,700
for 7 nights, 1 apartment
S$814 per night
includes taxes & fees
2-Story Townhome: Steps from the Sand & Gulf Views
Enjoy morning coffee or evening sunsets on the shared bayfront patio—complete with stunning water views.
Exceptional
(19 reviews)

Siesta Key Base | Walk to Beach | Free Activities

Siesta Key

7% off
S$3,377
for 7 nights, 1 apartment
S$482 per night
includes taxes & fees
Siesta Key Base | Walk to Beach | Free Activities
Exterior
Exceptional
(44 reviews)

Siesta Key Beachside Condo-direct beach access

Siesta Key

8% off
S$3,548
for 7 nights, 1 apartment
S$507 per night
includes taxes & fees
Siesta Key Beachside Condo-direct beach access
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$8,753
for 7 nights, 1 home
S$1,250 per night
includes taxes & fees
Waterfront 5BR Luxury Home – Pool, Spa, Boat Lift, Putting Green, Fire Pit
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$5,290
for 7 nights, 1 apartment
S$756 per night
includes taxes & fees
Bayfront 2025 Reno - 2 King Suites - Pool - Boat Dock - Walk to Beach & Pier
Terrace/patio
Exceptional
(8 reviews)

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

Bradenton

9% off
S$2,328
for 7 nights, 1 villa
S$333 per night
includes taxes & fees
For family fun or a romantic escape close to sarasota and the area"s beaches
Complex heated pool and private tennis court overlooking Crescent Beach!. (complex aerial view). What are you waiting for?!!
Wonderful
(145 reviews)

House of Sun: Beachfront | VIP Perks | Bunkbeds

Siesta Key

7% off
S$7,422
for 7 nights, 1 apartment
S$1,060 per night
includes taxes & fees
House of Sun: Beachfront | VIP Perks | Bunkbeds
Room
Exceptional
(7 reviews)

Private Suite with Lounge & Private Patio

Bradenton

8% off
S$863
for 7 nights, 1 apartment
S$123 per night
includes taxes & fees
Private Suite with Lounge & Private Patio
Pool
Excellent
(156 reviews)

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

Sarasota

8% off
S$1,087
for 7 nights, 1 room
S$155 per night
includes taxes & fees
Right on the Waterfront Marina - Suite 117 - 7150 N Tamiami Tail, Sarasota FL
A "close-up" view from the balcony.....
Exceptional
(104 reviews)

Siesta Sands Private Beach | Gulf Views | Htd Pool

Siesta Key

7% off
S$7,145
for 7 nights, 1 apartment
S$1,021 per night
includes taxes & fees
Siesta Sands Private Beach | Gulf Views | Htd Pool
Interior
Exceptional
(28 reviews)

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

Sarasota

8% off
S$4,782
for 7 nights, 1 home
S$683 per night
includes taxes & fees
Family Poolside Paradise on Quiet Cul-de-Sac 4.7 Miles from Siesta Key Beach
Private kitchen
Exceptional
(111 reviews)

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

Anna Maria

8% off
S$5,402
for 7 nights, 1 home
S$772 per night
includes taxes & fees
75 ft Canal Front Anna Maria House, Great for Boaters, Newly Renovated
Private kitchen
Exceptional
(67 reviews)

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

Bradenton

8% off
S$4,038
for 7 nights, 1 home
S$577 per night
includes taxes & fees
Ila's Beach House: Near IMG-Heated Salt Pool- Pets OK-Modern Organic Smart Home
  • Peace of mind

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  • 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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