Longboat Key holiday rentals

We found 11,929 holiday rentals — enter your dates for availability
Discover a selection of 16 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:18 Dec - 25 Dec

Interior
Four barstools and large area for eating
dining room with seating for 8
Living area
Exceptional
(87 reviews)

Large pool/spa home minutes from beach with arcade games and canal for fishing.

Bradenton

7% off
S$4,047
for 7 nights, 1 home
S$578 per night
includes taxes & fees
Large pool/spa home minutes from beach with arcade games and canal for fishing.
French doors to the lanai and 60 inch TV on the wall.
Quiet spot in paradise
Gumbo tree in front yard
Have your morning coffee on the lanai.
Exceptional
(92 reviews)

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

Bradenton

8% off
S$2,167
for 7 nights, 1 home
S$310 per night
includes taxes & fees
Quiet cozy home near Anna Maria Island, Robinson Preserve, DeSoto Nt’l Monument
View of River from house
Kitchen
Landscaping behind the Cut 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$3,495
for 7 nights, 1 home
S$499 per night
includes taxes & fees
Snead Island Cut Home - Oceanfront near Anna Maria , Boat docking, pet friendly
Shopping on Anna Maria Island is like discovering hidden gems!
Anna Maria, Florida's ocean is your ultimate fun zone!
Your ideal mix of style, convenience, and comfort is ready and waiting for you.
Pool
Exceptional
(56 reviews)

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

Bradenton

8% off
S$6,491
for 7 nights, 1 home
S$927 per night
includes taxes & fees
Luxury Family Escape: Spacious 4BR, Pool, Close to AMI, Dining & Attractions!
Outdoor dining
Pool
Living area
Exterior
Exceptional
(137 reviews)

6 Bedrooms - Waterfront,pool, dock, great for families. Big yard, lots of room.

Bradenton

5% off
S$12,716
for 7 nights, 1 home
S$1,817 per night
includes taxes & fees
6 Bedrooms - Waterfront,pool, dock, great for families. Big yard, lots of room.
Dining
Pool
Property grounds
Exterior
Exceptional
(39 reviews)

6 BR/5.5 Bth-Huge Heated Pool/Spa/Water Slide...Short -1 Min Walk to Beach

Holmes Beach

42% off
S$11,749
for 7 nights, 1 home
S$1,678 per night
includes taxes & fees
6 BR/5.5 Bth-Huge Heated Pool/Spa/Water Slide...Short -1 Min Walk to Beach
Living area
Interior
Living area
Terrace/patio
Wonderful
(49 reviews)

🌴 Peaceful Sarasota Home with Patio, 2BR, 2BA Near Lido Beach & Downtown

Sarasota

7% off
S$1,501
for 7 nights, 1 home
S$214 per night
includes taxes & fees
🌴 Peaceful Sarasota Home with Patio, 2BR, 2BA Near Lido Beach & Downtown
Property grounds
Pool
Room
Fitness facility
Excellent
(156 reviews)

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

Sarasota

8% off
S$1,051
for 7 nights, 1 room
S$150 per night
includes taxes & fees
Right on the Waterfront Marina - Suite 117 - 7150 N Tamiami Tail, Sarasota FL
Fitness facility
Outdoor dining
Heated waterfront pool
Marina
Very good
(164 reviews)

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

Sarasota

8% off
S$966
for 7 nights, 1 room
S$138 per night
includes taxes & fees
SARASOTA Waterfront hotel Room KING BED # 215 ON SARA BAY 7150 N Tamiami Trail
Terrace/patio
Resort Styled 5-bdrm waterfront w/Pool/Spa/FirePit/Putting Grn/Boat/Jet Ski Lift
Dinning Room Table that Seats 10!
Exterior
Wonderful
(16 reviews)

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

Bradenton

8% off
S$8,128
for 7 nights, 1 home
S$1,161 per night
includes taxes & fees
Waterfront 5BR Luxury Home – Pool, Spa, Boat Lift, Putting Green, Fire Pit
Interior
Private kitchen
Exterior
Interior
Exceptional
(63 reviews)

Charming Beach home sits amongst huge Banyan Trees, walk to beach’s & Pine Ave.

Anna Maria

8% off
S$3,881
for 7 nights, 1 home
S$554 per night
includes taxes & fees
Charming Beach home sits amongst huge Banyan Trees, walk to beach’s & Pine Ave.
Living area
Beach
King bed
Interior
Exceptional
(24 reviews)

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

Siesta Key

8% off
S$4,666
for 7 nights, 1 apartment
S$667 per night
includes taxes & fees
Good Vibrations- Stay right ON the beach in Siesta Key! Sleeps 6
Bathroom
Terrace/patio
Private kitchen
Bedroom #2- Queen mattress
Exceptional
(21 reviews)

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

Sarasota

8% off
S$2,035
for 7 nights, 1 home
S$291 per night
includes taxes & fees
Charming 2-bedroom house in the heart of Sarasota—A quaint nature escape
Private kitchen
Interior
Interior
Interior
Wonderful
(9 reviews)

Family Pool Home Near Anna Maria Island & IMG

Bradenton

7% off
S$2,682
for 7 nights, 1 home
S$383 per night
includes taxes & fees
Family Pool Home Near Anna Maria Island & IMG
Fully stocked kitchen
Screened porch
BBQ and Outdoor patio space
King bedroom
Exceptional
(44 reviews)

Island House Resort - Waterfront 2-bedroom condo directly on Siesta Key Beach!

Siesta Key

6% off
S$3,523
for 7 nights, 1 room
S$503 per night
includes taxes & fees
Island House Resort - Waterfront 2-bedroom condo directly on Siesta Key Beach!
Large dinning room
Desk/office space
Bonus sun room with cute fireplace (non-functional!)
Pool
Exceptional
(63 reviews)

Amazing heated pool & spa just minutes from Anna Maria Island

Bradenton

8% off
S$3,286
for 7 nights, 1 home
S$469 per night
includes taxes & fees
Amazing heated pool & spa just minutes from Anna Maria Island
spare bedding & pillows for the futon is in the closet.
Living area / king size bed with balcony, overlooking the beach.
Dining table looking into kitchenette, fridge, microwave, two burner stove.
Condo pool with tables and chairs and large shaded seating area!
Exceptional
(6 reviews)

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

Bradenton Beach

8% off
S$2,961
for 7 nights, 1 apartment
S$423 per night
includes taxes & fees
The Pelican's Perch, a Beachfront studio condo w/ balcony
Room
Pool
Exterior
Property grounds
Exceptional
(17 reviews)

New The BLUE HERON 3 bedroom oasis with heated pool

Bradenton

6% off
S$2,515
for 7 nights, 1 home
S$359 per night
includes taxes & fees
New The BLUE HERON 3 bedroom oasis with heated pool
Private kitchen
Beach
Exterior
Outdoor dining
Exceptional
(104 reviews)

Low Rider - Bottom Unit -

Bradenton Beach

8% off
S$4,468
for 7 nights, 1 home
S$638 per night
includes taxes & fees
Low Rider - Bottom Unit -
Enclosed patio brand new furniture (purchased June 2024)
Quiet and safe neighborhood for families to swim, walk, bike, and fish
Front Entrance
View of spacious main pool and clubhouse.  Dry sauna and gym inside.
Exceptional
(102 reviews)

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

Siesta Key

5% off
S$5,589
for 7 nights, 1 apartment
S$798 per night
includes taxes & fees
Gulf & Bay Club Bayside, 1st Floor, CLEAN, 5 STARS & EXCELLENT REVIEWS!
Private kitchen
Private rear patio
New Queen Bed with plenty of pillows to choose to your liking.
Entry shelves with extra beach towels, cooler, futon blankets, etc
Exceptional
(21 reviews)

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

Siesta Key

8% off
S$3,341
for 7 nights, 1 apartment
S$477 per night
includes taxes & fees
Siesta Key Beach Cottage-Prime Location! Walkable. Luxury Amenities & Comfort!
  • 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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