Best Vacation Homes in Longboat Key
Condo
10.0(211 Reviews)
1 Bedroom
1 Bath
6 Guests
800 ft²
Oceanfront
Hot Tub
Parking
Pool
CA $850/Night
7 Nights - CA $5,950
Apartment
10.0(6 Reviews)
2 Bedrooms
1 Bath
4 Guests
1259.38 ft²
Private Pool
Private Beach- Oceanfront
- Parking
CA $397/Night
7 Nights - CA $2,777
Apartment
9.2(350 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Pool
Ocean View
Balcony/Terrace
CA $283/Night
7 Nights - CA $1,982
Condo
10.0(136 Reviews)
1 Bedroom
1 Bath
6 Guests
800 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
CA $658/Night
7 Nights - CA $4,607
Apartment
10.0(2 Reviews)
1 Bedroom
1 Bath
4 Guests
409.03 ft²
- Private Beach
- Oceanfront
- Parking
- Pool
CA $481/Night
7 Nights - CA $3,369
Condo
10.0(132 Reviews)
1 Bedroom
1 Bath
4 Guests
330 ft²
- Parking
- Pool
- Ocean View
- Balcony/Terrace
CA $687/Night
7 Nights - CA $4,809
Condo
10.0(96 Reviews)
2 Bedrooms
2 Baths
6 Guests
1100 ft²
- Hot Tub
- Parking
- Pool
- Ocean View
CA $700/Night
7 Nights - CA $4,900
Apartment
10.0(93 Reviews)
1 Bedroom
1 Bath
4 Guests
330 ft²
- Parking
- Pool
- Ocean View
- Balcony/Terrace
CA $624/Night
7 Nights - CA $4,366
Longboat Key Luxury Rentals
Condo
10.0(3 Reviews)
2 Bedrooms
2 Baths
5 Guests
3130 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
CA $2,481/Night
7 Nights - CA $17,366
Condo
1 Bedroom
2 Baths
4 Guests
1172 ft²
- Hot Tub
- Parking
- Pool
- Ocean View
CA $2,189/Night
7 Nights - CA $15,320
House
6 Bedrooms
5 Baths
10 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
CA $1,957/Night
7 Nights - CA $13,698
Condo
3 Bedrooms
3 Baths
6 Guests
- Pool
- Ocean View
View
Kitchen
CA $1,442/Night
7 Nights - CA $10,091
Apartment
10.0(1 Review)
3 Bedrooms
2 Baths
6 Guests
1743.75 ft²
- Private Beach
- Oceanfront
- Parking
- Pool
CA $1,342/Night
7 Nights - CA $9,392
Apartment
8.5(2 Reviews)
3 Bedrooms
2 Baths
6 Guests
1743.75 ft²
- Private Beach
- Oceanfront
- Parking
- Pool
CA $1,342/Night
7 Nights - CA $9,392
Condo
9.8(42 Reviews)
3 Bedrooms
2 Baths
6 Guests
1896 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
CA $1,307/Night
7 Nights - CA $9,148
Condo
10.0(15 Reviews)
3 Bedrooms
2 Baths
6 Guests
1399 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
CA $1,304/Night
7 Nights - CA $9,125
Longboat Key Pet Friendly Vacation Rentals
Condo
10.0(11 Reviews)
1 Bedroom
1 Bath
4 Guests
657 ft²
- Parking
- Balcony/Terrace
- Kitchen
Air Conditioner
CA $188/Night
7 Nights - CA $1,314
House
3 Bedrooms
1 Bath
7 Guests
1593.06 ft²
- Balcony/Terrace
- View
- Air Conditioner
Internet
CA $271/Night
7 Nights - CA $1,894
Condo
10.0(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
1096 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
CA $530/Night
7 Nights - CA $3,712
New
Apartment
2 Bedrooms
2 Baths
7 Guests
1259.38 ft²
- Private Beach
- Oceanfront
- Parking
- Pool
CA $557/Night
7 Nights - CA $3,896
House
10.0(1 Review)
2 Bedrooms
2 Baths
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $415/Night
7 Nights - CA $2,902
Condo
10.0(1 Review)
2 Bedrooms
2 Baths
5 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
CA $376/Night
7 Nights - CA $2,633
House
10.0(1 Review)
2 Bedrooms
2 Baths
4 Guests
1700 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
CA $375/Night
7 Nights - CA $2,622
House
10.0(1 Review)
2 Bedrooms
2 Baths
6 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
CA $326/Night
7 Nights - CA $2,284
Longboat Key Large Vacation Homes
Villa
9.6(4 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Air Conditioner
- Internet
Child Friendly
Laundry
CA $934/Night
7 Nights - CA $6,541
Apartment
10.0(1 Review)
21 Bedrooms
2 Baths
4 Guests
1194.79 ft²
- Private Beach
- Oceanfront
- Parking
- Pool
CA $576/Night
7 Nights - CA $4,033
Villa
2 Bedrooms
2 Baths
2 Guests
900 ft²
- Air Conditioner
- Internet
Pet Friendly- Child Friendly
CA $250/Night
7 Nights - CA $1,752
Apartment
8.7(100 Reviews)
21 Bedrooms
11 Baths
30 Guests
510.21 ft²
- Private Beach
- Oceanfront
- Parking
- Pool
CA $405/Night
7 Nights - CA $2,833
House
9.8(6 Reviews)
3 Bedrooms
3 Baths
10 Guests
2019 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Parking
CA $678/Night
7 Nights - CA $4,747
House
5 Bedrooms
6 Baths
12 Guests
5350 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
CA $1,158/Night
7 Nights - CA $8,106
Condo
4 Bedrooms
4 Baths
10 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
CA $1,063/Night
7 Nights - CA $7,440
Villa
3 Bedrooms
2 Baths
6 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
CA $869/Night
7 Nights - CA $6,083
Why Choose Rent By Owner for your Longboat Key Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Popular Areas for Longboat Key Vacation Rentals
Where are the best neighborhoods to stay in Longboat Key?
When selecting a neighborhood to stay in Longboat Key, Florida, you’ll discover a variety of charming and convenient options that cater to your preferences. From tranquil areas offering serene beachfront views to lively communities close to local amenities, each neighborhood provides a unique experience. Whether you’re seeking a peaceful retreat or an active ambiance, finding the perfect location in Longboat Key ensures your vacation is both comfortable and memorable. Explore the diverse neighborhoods and choose the ideal setting for your next getaway to this beautiful Florida destination.
Longbeach Village
This charming neighborhood offers a quaint atmosphere with scenic views and easy access to the water, making it an ideal choice for those seeking a peaceful retreat in Longboat Key. Here, you can enjoy a relaxed vibe while staying close to the area's natural beauty and local amenities.
View 2382+ Rentals in Longbeach VillageBay Isles
Known for its upscale environment and lush landscapes, Bay Isles provides a luxurious setting in the region for your stay. Here, you’ll find an exclusive atmosphere combined with convenient proximity to key attractions, perfect for a refined vacation experience.
View 819+ Rentals in Bay IslesBest Times to Visit Longboat Key
When should you plan your Vacation Rentals stay?
Choosing the ideal time to visit this destination can enhance your experience, as the region offers different climates and crowd levels throughout the year, making it important to consider seasonal factors when booking your vacation rentals.
Peak Season Highlights
Spring (March to May)
During this time, the weather warms up, making it ideal for enjoying outdoor activities and relaxing by the Gulf Coast.
Average Temperature Daytime: 78°F - 85°F - Nighttime: 60°F - 70°F
Winter (December to February)
This quieter season offers cooler temperatures and fewer crowds, perfect for those seeking a peaceful coastal retreat in the region.
Average Temperature Daytime: 65°F - 75°F - Nighttime: 50°F - 60°F
Off-Season Highlights
Summer (June to August)
While temperatures soar, summer brings vibrant local events and opportunities for water-based adventures, with fewer visitors around.
Average Temperature Daytime: 88°F - 90°F - Nighttime: 75°F - 78°F
Fall (September to November)
Enjoy the cooler, pleasant weather and lower rates during this season, as the area transitions from summer to winter.
Average Temperature Daytime: 75°F - 82°F - Nighttime: 55°F - 65°F
Weekly Weather Forecast for Longboat Key
How to Book Your Longboat Key Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy access to private or community swimming pools that overlook the scenic surroundings.
- Relax in landscaped outdoor areas with lush gardens and shaded seating options.
- Utilize outdoor grilling stations for preparing meals while enjoying the fresh air.
- Make the most of direct beach access to walk along pristine sands and soak up the sun.
- Take advantage of outdoor showers to rinse off after a day at the shoreline or pool.
- Experience the convenience of on-site tennis courts for active recreation during your stay.
- Benefit from available boat docks or piers, perfect for exploring the region by water.
Top Attractions Around Longboat Key
What attractions are nearby?
Within this charming coastal area, you can enjoy a variety of outdoor activities such as relaxing on pristine beaches, exploring local parks, or engaging in water sports just moments from your vacation rental.
Family Activities
- Beach Exploration: Spend a relaxing day building sandcastles and swimming at the expansive beaches, perfect for family fun in this coastal destination.
- Sunset Park Walks: Enjoy scenic strolls with your loved ones along waterfront parks that offer stunning views and a peaceful atmosphere for all ages.
- Wildlife Viewing: Discover local bird species and marine life just steps from your vacation rental, making it an educational experience for children.
- Water Sports Activities: Try kayaking, paddleboarding, or boat rentals available nearby to introduce your family to aquatic adventures in the region.
Adult Activities
- Sailing and Boating: You can enjoy exploring the scenic waterways of Longboat Key through guided boat tours or rent a boat to experience the region’s vibrant marine life firsthand.
- Golfing: Tee off at world-class golf courses nearby, where the lush fairways and coastal views provide an ideal setting for a relaxing day on the links.
- Fishing: Engage in freshwater or saltwater fishing excursions designed for all skill levels, offering the chance to catch local species while appreciating the area's natural beauty.
- Sunset Cruises: Indulge in a romantic sunset cruise along the Gulf of Mexico, taking in the breathtaking colors while enjoying the tranquil ocean breeze.
Other Places to Stay in Longboat Key, FL
Jewfish Key
Beer Can Island
Longbeach Village
Quick Point Nature Reserve
Cannons Marina
Harborside Golf Course at Longboat Key Club
Islandside Golf Course at Longboat Key Club
Bay Isles
Longboat Key Beaches
Longboat Key Travel Tips
How Can You Make the Most of Your Stay?
- Plan Your Activities Ahead: Take advantage of the area's serene beaches and nearby outdoor pursuits by scheduling your excursions in advance to maximize your relaxation and adventure time.
- Choose a Prime Location: Opt for vacation rentals close to the coast or local amenities to easily enjoy the scenic beauty and vibrant community atmosphere here.
- Explore Local Dining Options: Immerse yourself in the region's culinary scene by discovering nearby restaurants and cafes that showcase the area's fresh seafood and regional flavors.
- Make Use of Nearby Recreational Spots: Enhance your stay by visiting surrounding parks, golf courses, or water activities that allow you to experience the best of this coastal destination.
Transportation Options
- Rental Car Services: You can conveniently explore the area with rental car agencies that provide a variety of vehicles for your comfort and flexibility.
- Public Transportation: Local bus services offer an affordable way to navigate this coastal destination without the hassle of driving.
- Taxis and Rideshare Options: Taxis and rideshare apps like Uber and Lyft are readily available, offering quick and reliable transportation around here.
- Bicycle Rentals: Renting a bicycle allows you to enjoy scenic views and easy access to nearby beaches and attractions in this region.
Local Customs Options
- Beach Etiquette: Respect the pristine natural environment by following local guidelines for beach behavior, including designated swimming areas and protecting wildlife.
- Shell Collecting: When exploring the shoreline, be mindful to collect shells responsibly, ensuring you do not disturb the native ecosystems or leave debris behind.
- Water Sports Customs: Engage in water activities with awareness of regional safety norms, such as observing flags indicating water conditions and respecting local boating regulations.
- Community Events and Festivals: Participate in seasonal gatherings and festivals that celebrate here’s coastal culture, fostering a deeper appreciation of the area's traditions and community spirit.
Frequently Asked Questions About Longboat Key?
1. What are the top vacation rentals in Longboat Key?
There are a lot of options in Longboat Key. If you plan on staying in the Longboat Key area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Longboat Key:
- Are you ready for a luxury 5-floor penthouse 60 ft from water, 207 reviews
- 50 ft from sand, Private Island 125 +review
- Island Time!
- Beautiful, renovated Gulf Front at Sand Cay with private beach on Longboat
- THE BEACH CONDO #107 BEACHFRONT FULL VIEW
- Upscale Beachplace Condo.availability starting in May 2026.please inquire
- Unit #210 Sand Cay Beach Resort Pool View
- Unit #110 Sand Cay Beach Pool View
- Beachcomber unit 204
- Longboat Key Waterfront 3BR house w/Pool in most desirable Country Club Shores
2. How many vacation rentals have private pools in Longboat Key?
There are 93 vacation rentals with private pools near Longboat Key. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Longboat Key are best for families?
If you are looking for a family-friendly vacation home in Longboat Key, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Longboat Key:
4. How many Rentbyowner vacation rentals are available in Longboat Key?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 820 in the Longboat Key area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Longboat Key.
5. What is the cancellation policy for vacation rentals in Longboat Key?
Cancellation policies vary by property, so it's essential to review the specific listing details before booking. Contact the property owner if you need clarification on their policy or any potential fees involved.
6. Are there any additional fees associated with my stay in Longboat Key vacation rentals?
Additional fees such as cleaning charges, security deposits, or service fees are often outlined in the listing details. Be sure to read the full description and reach out to the owner if you have questions about extra costs.
7. How do I know if the vacation rental has the amenities I need?
Property listings include detailed descriptions of amenities available, so review these carefully before booking. If you require specific features, contact the owner directly to confirm their availability during your stay.
8. What is the process for checking in and checking out of a Longboat Key vacation rental?
Check-in and check-out procedures are specified in each listing, including key collection methods and checkout times. Reach out to the owner for instructions if they are not clearly provided or if you need special arrangements.
9. Is there a minimum stay requirement for booking vacation rentals in this destination?
Minimum stay requirements depend on the individual property. Make sure to verify this information in the listing details or contact the owner directly to ensure your travel plans align with their policies.
Longboat Key Top Rated Vacation Rentals
Condo
10.0(38 Reviews)
2 Bedrooms
2 Baths
4 Guests
1503 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
CA $351/Night
7 Nights - CA $2,456
Condo
10.0(36 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
CA $638/Night
7 Nights - CA $4,462
Condo
10.0(24 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
CA $629/Night
7 Nights - CA $4,401
Condo
10.0(23 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
CA $691/Night
7 Nights - CA $4,837
House
10.0(20 Reviews)
3 Bedrooms
3 Baths
6 Guests
2000 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
CA $630/Night
7 Nights - CA $4,409
House
10.0(18 Reviews)
3 Bedrooms
2 Baths
6 Guests
2075 ft²
- Private Pool
- Parking
- Pool
- Ocean View
CA $507/Night
7 Nights - CA $3,545
New
Condo
10.0(16 Reviews)
1 Bedroom
1 Bath
4 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
CA $439/Night
7 Nights - CA $3,070
Condo
10.0(12 Reviews)
2 Bedrooms
2 Baths
4 Guests
1200 ft²
- Parking
- Pool
- Ocean View
- Balcony/Terrace
CA $849/Night
7 Nights - CA $5,943
