Longboat Key holiday rentals

We found 12,051 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:1 Jan - 8 Jan

Outdoor dining
Living area
Pool
Dining
Exceptional
(81 reviews)

Charming Coastal Oasis 2Bed/2 Bath Cottage Close to Beach and Downtown-Southgate

Sarasota

8% off
S$3,632
for 7 nights, 1 cottage
S$519 per night
includes taxes & fees
Charming Coastal Oasis 2Bed/2 Bath Cottage Close to Beach and Downtown-Southgate
Living room with connected enclosed patio
Sundeck on rooftop with partial ocean views
Fireplace, large ceiling fan, and HDTV
Main bedroom with direct access to enclosed balcony
Exceptional
(14 reviews)

Sundeck with Ocean View, Private Access to Beach & 500ft to the Village

Siesta Key

8% off
S$7,386
for 7 nights, 1 apartment
S$1,055 per night
includes taxes & fees
Sundeck with Ocean View, Private Access to Beach & 500ft to the Village
Living area
Beach
King bed
Interior
Exceptional
(25 reviews)

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

Siesta Key

8% off
S$3,960
for 7 nights, 1 apartment
S$566 per night
includes taxes & fees
Good Vibrations- Stay right ON the beach in Siesta Key! Sleeps 6
Property grounds
Beach chairs are offered for our guests in the private beach area of our complex
Pool
Terrace/patio
Exceptional
(99 reviews)

Great rates for September! SIESTA KEY GULF 2 bed 2 bath condo Jamaica Royale 104

Siesta Key

8% off
S$5,138
for 7 nights, 1 apartment
S$734 per night
includes taxes & fees
Great rates for September! SIESTA KEY GULF 2 bed 2 bath condo Jamaica Royale 104
Large dining room opens to living area, offering seamless entertaining space.
Sophisticated and serene Mediterranean beach home.
Private, heated pool and spa with canal views and your own private dock.
75" TV perfect for movie nights.
Exceptional
(14 reviews)

Casa del Siesta— Mediterranean Luxury by the Beach with Pool, Spa & Private Dock

Siesta Key

7% off
S$9,663
for 7 nights, 1 home
S$1,380 per night
includes taxes & fees
Casa del Siesta— Mediterranean Luxury by the Beach with Pool, Spa & Private Dock
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$6,052
for 7 nights, 1 home
S$865 per night
includes taxes & fees
Luxury Family Escape: Spacious 4BR, Pool, Close to AMI, Dining & Attractions!
Landscaping behind the Cut House
Kitchen
Rainbow at The Cut House
Manatee River with 120 ft dock
Exceptional
(64 reviews)

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

Palmetto

8% off
S$4,090
for 7 nights, 1 home
S$584 per night
includes taxes & fees
Snead Island Cut Home - Oceanfront near Anna Maria , Boat docking, pet friendly
Living area
Private kitchen
Interior
Living area
Exceptional
(69 reviews)

Waterfront/Kayak with Manatees/Heated Pool/Bikes/Firepit/Fish/close to Beaches

Bradenton

7% off
S$4,444
for 7 nights, 1 home
S$635 per night
includes taxes & fees
Waterfront/Kayak with Manatees/Heated Pool/Bikes/Firepit/Fish/close to Beaches
Outdoor fire pit. Please note guests are responsible for refilling propane
additional bar area seating
sliding door in kitchen leads to patio area
Pool
Exceptional
(129 reviews)

HEATED pool, bike to Siesta, quiet street, 1 MILE to SK beach, kayaks & bikes

Sarasota

5% off
S$4,234
for 7 nights, 1 home
S$605 per night
includes taxes & fees
HEATED pool, bike to Siesta, quiet street, 1 MILE to SK beach, kayaks & bikes
Have your morning coffee on the lanai.
Quiet spot in paradise
Gumbo tree in front yard
Patio French door with keypad left of door.
Exceptional
(92 reviews)

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

Bradenton

8% off
S$2,209
for 7 nights, 1 home
S$316 per night
includes taxes & fees
Quiet cozy home near Anna Maria Island, Robinson Preserve, DeSoto Nt’l Monument
Private kitchen
Beach
Living area
Room
Exceptional
(150 reviews)

Villas By The Sea #2, Anna Maria Island Condo, one block from beach, heated pool

Bradenton Beach

8% off
S$2,457
for 7 nights, 1 apartment
S$351 per night
includes taxes & fees
Villas By The Sea #2, Anna Maria Island Condo, one block from beach, heated pool
Private kitchen
Marina
Property grounds
Exterior
Exceptional
(43 reviews)

Siesta Key Beachside Condo-direct beach access

Siesta Key

8% off
S$3,573
for 7 nights, 1 apartment
S$510 per night
includes taxes & fees
Siesta Key Beachside Condo-direct beach access
Living area
Terrace/patio
Private kitchen
Room
Exceptional
(7 reviews)

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

Bradenton

9% off
S$2,628
for 7 nights, 1 villa
S$375 per night
includes taxes & fees
For family fun or a romantic escape close to sarasota and the area"s beaches
Private kitchen
Property grounds
Pool
Beach
Exceptional
(38 reviews)

Perfect 1-bedroom condo with AC in Bradenton Beach

Bradenton Beach

8% off
S$3,208
for 7 nights, 1 apartment
S$458 per night
includes taxes & fees
Perfect 1-bedroom condo with AC in Bradenton Beach
Outdoor dining
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$1,091
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
Bedroom #2- Queen mattress
Terrace/patio
Living area
Bathroom
Exceptional
(21 reviews)

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

Sarasota

8% off
S$2,392
for 7 nights, 1 home
S$342 per night
includes taxes & fees
Charming 2-bedroom house in the heart of Sarasota—A quaint nature escape
Terrace/patio
Private kitchen
Dining
Living area
Exceptional
(65 reviews)

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

Bradenton

8% off
S$4,467
for 7 nights, 1 home
S$638 per night
includes taxes & fees
Ila's Beach House: Near IMG-Heated Salt Pool- Pets OK-Modern Organic Smart Home
Outdoor dining
Living area
Room
Private kitchen
Exceptional
(106 reviews)

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

Bradenton

6% off
S$2,267
for 7 nights, 1 apartment
S$324 per night
includes taxes & fees
Shorewalk The Palm Condo 2Bed/2Bath Close to IMG / Beach
Front Entrance
Quiet and safe neighborhood for families to swim, walk, bike, and fish
Enclosed patio brand new furniture (purchased June 2024)
Boat/Fishing Deck
Exceptional
(102 reviews)

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

Siesta Key

5% off
S$4,893
for 7 nights, 1 apartment
S$699 per night
includes taxes & fees
Gulf & Bay Club Bayside, 1st Floor, CLEAN, 5 STARS & EXCELLENT REVIEWS!
Heated waterfront pool
Outdoor dining
Waterfront restaurant on premisis with live music
Marina
Very good
(164 reviews)

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

Sarasota

8% off
S$1,078
for 7 nights, 1 room
S$154 per night
includes taxes & fees
SARASOTA Waterfront hotel Room KING BED # 215 ON SARA BAY 7150 N Tamiami Trail
third bedroom details
Plush greens outside of the pool area
Exterior
sitting area by coffee station
Exceptional
(23 reviews)

Free Early Check-in / Min to Beaches/ Heated pool

Bradenton

8% off
S$3,336
for 7 nights, 1 home
S$477 per night
includes taxes & fees
Free Early Check-in / Min to Beaches/ Heated pool
Room
Terrace/patio
Interior
Interior
Exceptional
(13 reviews)

Gracie's Cottage 15 min to Beach

Bradenton

8% off
S$3,175
for 7 nights, 1 home
S$454 per night
includes taxes & fees
Gracie's Cottage 15 min to Beach
Dining table + 2 barstools for extra seating
Enclosed patio area with private pool
Interior
Property grounds
Exceptional
(57 reviews)

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

Sarasota

5% off
S$4,094
for 7 nights, 1 home
S$585 per night
includes taxes & fees
Serene yard and pool, 1 mile to beach, pets OK, patio TV, Kayaks
Outdoor dining
Beach
Private kitchen
Room
Exceptional
(105 reviews)

Low Rider - Bottom Unit -

Bradenton Beach

8% off
S$4,460
for 7 nights, 1 home
S$637 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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