Best Vacation Homes in Longboat Key
8 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Pool
R12,123/Night
For 7 Nights R84,861
R5,091/Night
For 7 Nights R35,635
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Fireplace/Heating
- Pool
R6,917/Night
For 7 Nights R48,426
6 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Fireplace/Heating
- Pool
R9,670/Night
For 7 Nights R67,696
1259.38 ft²
4 Guests
2 Bedrooms
1 Bathroom
Apartment
- Private Pool
- Private Beach
- Oceanfront
R4,617/Night
For 7 Nights R32,322
700 ft²
6 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Fireplace/Heating
- Pool
R7,067/Night
For 7 Nights R49,471
1250 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Fireplace/Heating
- Pool
- Ocean View
R6,001/Night
For 7 Nights R42,014
1569 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Hot Tub
- Fireplace/Heating
- Pool
R5,666/Night
For 7 Nights R39,665
Longboat Key Luxury Rentals
6 Guests
2 Bedrooms
2 Bathrooms
Condo
- Air Conditioner
- Internet
- Child Friendly
Unlock the Best Price
3130 ft²
5 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Hot Tub
- Fireplace/Heating
R34,770/Night
For 7 Nights R243,389
R26,432/Night
For 7 Nights R185,026
1172 ft²
4 Guests
1 Bedroom
2 Bathrooms
Ocean View
Condo
- Hot Tub
- Fireplace/Heating
- Pool
R25,472/Night
For 7 Nights R178,303
10 Guests
6 Bedrooms
5 Bathrooms
Ocean View
House
- Private Pool
- Hot Tub
- Fireplace/Heating
R23,569/Night
For 7 Nights R164,989
5350 ft²
12 Guests
5 Bedrooms
6 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Fireplace/Heating
R16,942/Night
For 7 Nights R118,586
1700 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Ocean View
Condo
- Private Pool
- Oceanfront
- Fireplace/Heating
R16,401/Night
For 7 Nights R114,801
5300 ft²
8 Guests
4 Bedrooms
5 Bathrooms
Family Friendly
House
- Private Pool
- Hot Tub
- Fireplace/Heating
R16,321/Night
For 7 Nights R114,246
Longboat Key Pet Friendly Vacation Rentals
657 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Condo
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
R3,249/Night
For 7 Nights R22,745
1593.06 ft²
7 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
R3,149/Night
For 7 Nights R22,043
1096 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Fireplace/Heating
- Pool
R5,330/Night
For 7 Nights R37,315
699.65 ft²
6 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Private Beach
- Oceanfront
- Pool
R7,190/Night
For 7 Nights R50,335
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
R6,655/Night
For 7 Nights R46,583
1700 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Fireplace/Heating
R4,637/Night
For 7 Nights R32,453
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
R4,489/Night
For 7 Nights R31,425
1500 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Fireplace/Heating
- Pool
R3,778/Night
For 7 Nights R26,449
Longboat Key Large Vacation Homes
2000 ft²
8 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Villa
- Hot Tub
- Spa
- Fireplace/Heating
R14,557/Night
For 7 Nights R101,895
1194.79 ft²
4 Guests
21 Bedrooms
2 Bathrooms
Apartment
- Private Beach
- Oceanfront
- Fireplace/Heating
R6,706/Night
For 7 Nights R46,942
1145 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Villa
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R4,465/Night
For 7 Nights R31,262
510.21 ft²
30 Guests
21 Bedrooms
11 Bathrooms
Ocean View
Apartment
- Private Beach
- Oceanfront
- Fireplace/Heating
R5,255/Night
For 7 Nights R36,777
6 Guests
2 Bedrooms
2 Bathrooms
Villa
- Fireplace/Heating
- Air Conditioner
- Internet
R12,998/Night
For 7 Nights R90,995
900 ft²
2 Guests
2 Bedrooms
2 Bathrooms
Couples Retreat
Villa
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
R3,060/Night
For 7 Nights R21,423
2019 ft²
10 Guests
3 Bedrooms
3 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Hot Tub
R7,694/Night
For 7 Nights R53,860
1 ft²
12 Guests
4 Bedrooms
4 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Fireplace/Heating
R13,100/Night
For 7 Nights R91,697
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 2398+ 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 810+ 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.
Explore and book the perfect rental in Longboat Key
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
- Take a peek awesome reviews 50 feet from sand
- 50 ft from sand, Private Island 125 +review
- Sun-Kissed Memories!
- 1 Week left April 18 of a kind home right on the beach then booked till July
- Client texted view crazy
- Beautiful, renovated Gulf Front at Sand Cay with private beach on Longboat
- THE BEACH CONDO #107 BEACHFRONT FULL VIEW
- Unit #218 Sand Cay Beach Resort Gulf Front
- Upscale Beachplace Condo.availability starting in May 2026.please inquire
2. How many vacation rentals have private pools in Longboat Key?
There are 96 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 842 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
800 ft²
6 Guests
1 Bedroom
1 Bathroom
Ocean View
Condo
- Oceanfront
- Hot Tub
- Fireplace/Heating
R9,615/Night
For 7 Nights R67,304
800 ft²
6 Guests
1 Bedroom
1 Bathroom
Ocean View
Condo
- Fireplace/Heating
- Pool
- Ocean View
R6,042/Night
For 7 Nights R42,292
800 ft²
6 Guests
1 Bedroom
1 Bathroom
Ocean View
Condo
- Oceanfront
- Fireplace/Heating
- Pool
R5,934/Night
For 7 Nights R41,541
330 ft²
4 Guests
1 Bedroom
1 Bathroom
Ocean View
Condo
- Fireplace/Heating
- Pool
- Ocean View
R6,878/Night
For 7 Nights R48,149
800 ft²
6 Guests
1 Bedroom
1 Bathroom
Ocean View
Condo
- Fireplace/Heating
- Pool
- Ocean View
R5,987/Night
For 7 Nights R41,900
1100 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Hot Tub
- Fireplace/Heating
- Pool
R11,178/Night
For 7 Nights R78,236
330 ft²
4 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Fireplace/Heating
- Pool
- Ocean View
R7,382/Night
For 7 Nights R51,673
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Fireplace/Heating
- Pool
R9,743/Night
For 7 Nights R68,202
