Longboat Key holiday rentals

We found 11,833 holiday rentals — enter your dates for availability
Discover a selection of 20 homes, 18 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:27 Nov - 4 Dec

Your ideal mix of style, convenience, and comfort is ready and waiting for you.
Anna Maria, Florida's ocean is your ultimate fun zone!
Shopping on Anna Maria Island is like discovering hidden gems!
Pool
Exceptional
(56 reviews)

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

Bradenton

7% off
S$4,899
for 7 nights, 1 home
S$700 per night
includes taxes & fees
Luxury Family Escape: Spacious 4BR, Pool, Close to AMI, Dining & Attractions!
nm
Kitchen area
Exterior detail
Outdoor dining
Exceptional
(242 reviews)

Great Value!!! Immaculate, minutes from the beach, With heated pool !!

Sarasota

5% off
S$2,362
for 7 nights, 1 home
S$337 per night
includes taxes & fees
Great Value!!! Immaculate, minutes from the beach, With heated pool !!
Exterior detail
Property grounds
Terrace/patio
Living area
Exceptional
(101 reviews)

Sarasota Cozy & Clean, Near #1 Beach Siesta in SouthGate Neighborhood

Sarasota

8% off
S$1,180
for 7 nights, 1 apartment
S$169 per night
includes taxes & fees
Sarasota Cozy & Clean, Near #1 Beach Siesta in SouthGate Neighborhood
Outdoor dining
Pool
Living area
Property grounds
Exceptional
(137 reviews)

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

Bradenton

8% off
S$10,277
for 7 nights, 1 home
S$1,468 per night
includes taxes & fees
6 Bedrooms - Waterfront,pool, dock, great for families. Big yard, lots of room.
Terrace/patio
Interior
Living area
Room
Exceptional
(46 reviews)

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

Sarasota

7% off
S$1,517
for 7 nights, 1 home
S$217 per night
includes taxes & fees
🌴 Peaceful Sarasota Home with Patio, 2BR, 2BA Near Lido Beach & Downtown
Heated waterfront pool
Outdoor dining
Fitness facility
Marina
Very good
(164 reviews)

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

Sarasota

7% off
S$883
for 7 nights, 1 room
S$126 per night
includes taxes & fees
SARASOTA Waterfront hotel Room KING BED # 215 ON SARA BAY 7150 N Tamiami Trail
Living area
Private kitchen
Exterior
Room
Exceptional
(11 reviews)

Siesta Vista, Spacious Waterfront Home. One Block to Beach & Village. Roof Deck!

Siesta Key

6% off
S$11,490
for 7 nights, 1 home
S$1,641 per night
includes taxes & fees
Siesta Vista, Spacious Waterfront Home. One Block to Beach & Village. Roof Deck!
Living area
Interior
Dining
Living area
Exceptional
(18 reviews)

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

Bradenton

11% off
S$4,703
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
Aerial view with Gulf of Mexico in the backround.
Quiet Beaches.
Exterior
Pool
Exceptional
(280 reviews)

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

Bradenton Beach

7% off
S$4,690
for 7 nights, 1 home
S$670 per night
includes taxes & fees
Beach Access, heated pool, and new spa. Pickleball and playground along the bay!
Terrace/patio
Private kitchen
Living area
Marina
Exceptional
(110 reviews)

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

Anna Maria

8% off
S$4,265
for 7 nights, 1 home
S$609 per night
includes taxes & fees
75 ft Canal Front Anna Maria House, Great for Boaters, Newly Renovated
Private kitchen
Beautiful entrance to your private beach
Living area
Interior
Exceptional
(85 reviews)

Private Villa Beachside complex, Siesta Key private beach access 2br/2ba patio

Siesta Key

8% off
S$3,354
for 7 nights, 1 villa
S$479 per night
includes taxes & fees
Private Villa Beachside complex, Siesta Key private beach access 2br/2ba patio
Private kitchen
Sports court
Interior
Interior
Exceptional
(45 reviews)

Beautiful Blue Beach House Kids & Pets OK Aug, Sept, Oct, Nov, Dec DISCOUNTS! Beautiful Blue Beach House/AMIsland White Sand Beaches

Bradenton

6% off
S$2,163
for 7 nights, 1 home
S$309 per night
includes taxes & fees
Beautiful Blue Beach House Kids & Pets OK Aug, Sept, Oct, Nov, Dec DISCOUNTS! Beautiful Blue Beach House/AMIsland White Sand Beaches
Exterior
Beach
Property grounds
Dining
Wonderful
(16 reviews)

Luxury Waterfront Views / Pool / 1400sf / Minutes to Beach

Siesta Key

8% off
S$3,786
for 7 nights, 1 apartment
S$541 per night
includes taxes & fees
Luxury Waterfront Views / Pool / 1400sf / Minutes to Beach
Marina
Outdoor dining
Pool
Fitness facility
Very good
(174 reviews)

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

Sarasota

7% off
S$1,086
for 7 nights, 1 room
S$155 per night
includes taxes & fees
Sarasota “Deluxe King Waterfront Suite” #201 At the Hotel at 7150 N TAMIAMI TR
Bathroom
Terrace/patio
Private kitchen
Bedroom #2- Queen mattress
Exceptional
(20 reviews)

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

Sarasota

8% off
S$1,553
for 7 nights, 1 home
S$222 per night
includes taxes & fees
Charming 2-bedroom house in the heart of Sarasota—A quaint nature escape
Pool
Private kitchen
Terrace/patio
Living area
Exceptional
(62 reviews)

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

Bradenton

7% off
S$2,878
for 7 nights, 1 home
S$411 per night
includes taxes & fees
Ila's Beach House: Near IMG-Heated Salt Pool- Pets OK-Modern Organic Smart Home
Beach
Front door and porch area
Front of building
Robin Hood Rentals golf carts bikes etc
Exceptional
(15 reviews)

Siesta Key Village • Pool • Walk to Beach • Pets

Siesta Key

8% off
S$2,498
for 7 nights, 1 apartment
S$357 per night
includes taxes & fees
Siesta Key Village • Pool • Walk to Beach • Pets
Interior
Sunset Royale Condominiums
Room
Interior
Exceptional
(52 reviews)

Get here fast, then take it slow... Right — ON — Siesta Beach at Condo Kokomo!

Siesta Key

7% off
S$2,721
for 7 nights, 1 apartment
S$389 per night
includes taxes & fees
Get here fast, then take it slow... Right — ON — Siesta Beach at Condo Kokomo!
Living area
Interior
Dining
Interior
Exceptional
(42 reviews)

Luxury condo located directly on Siesta Key Beach

Siesta Key

8% off
S$3,163
for 7 nights, 1 apartment
S$452 per night
includes taxes & fees
Luxury condo located directly on Siesta Key Beach
Condo pool with tables and chairs and large shaded seating area!
Living area / king size bed with balcony, overlooking the beach.
Dining table looking into kitchenette, fridge, microwave, two burner stove.
spare bedding & pillows for the futon is in the closet.
Exceptional
(5 reviews)

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

Bradenton Beach

12% off
S$2,718
for 7 nights, 1 apartment
S$388 per night
includes taxes & fees
The Pelican's Perch, a Beachfront studio condo w/ balcony
Exterior
Pool
Room
Terrace/patio
Exceptional
(17 reviews)

New The BLUE HERON 3 bedroom oasis with heated pool

Bradenton

7% off
S$2,310
for 7 nights, 1 home
S$330 per night
includes taxes & fees
New The BLUE HERON 3 bedroom oasis with heated pool
Exterior
Beach
Room
Private kitchen
Exceptional
(102 reviews)

Low Rider - Bottom Unit -

Bradenton Beach

8% off
S$4,581
for 7 nights, 1 home
S$654 per night
includes taxes & fees
Low Rider - Bottom Unit -
Boat/Fishing Deck
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$4,452
for 7 nights, 1 apartment
S$636 per night
includes taxes & fees
Gulf & Bay Club Bayside, 1st Floor, CLEAN, 5 STARS & EXCELLENT REVIEWS!
Property grounds
Enclosed patio area with private pool
Interior
Pool
Exceptional
(55 reviews)

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

Sarasota

5% off
S$3,443
for 7 nights, 1 home
S$492 per night
includes taxes & fees
Serene yard and pool, 1 mile to beach, pets OK, patio TV, Kayaks
  • 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. Siesta Key Beach and Lido 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)
  • 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)
  • Links on Longboat (7 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:

  • Siesta Key Beach (12 mi / 19.4 km)
  • Lido Beach (8.8 mi / 14.2 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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