Longboat Key, FL Resort Rentals

Longboat Key Resorts

Resort

Florida's Longboat Key Paradise

10.0

Exceptional

(2 Reviews)

2 Baths 6 Guests

US $500/Night 7 Nights - US $3,500

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Hotel

The St. Regis Longboat Key Resort

8.8

Fabulous

(24 Reviews)

11 Baths 673 ft²

US $741/Night 7 Nights - US $5,187

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Highly Rated

Resort

Zota Beach Resort

9.0

Exceptional

(1011 Reviews)

1 Bath

US $315/Night 7 Nights - US $2,205

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Waterfront 2-Bedroom Retreat in Longboat Key

New

Apartment

Waterfront 2-Bedroom Retreat in Longboat Key

10.0

Exceptional

(1 Review)

2 Bedrooms 2 Baths 4 Guests 1072 ft²

US $267/Night 7 Nights - US $1,871

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LaPlaya 202E Catch the gentle Gulf breezes on your private balcony beneath the swaying palms

Apartment

LaPlaya 202E Catch the gentle Gulf breezes on your private balcony beneath the swaying palms

10.0

Exceptional

(6 Reviews)

2 Bedrooms 1 Bath 4 Guests 1259.38 ft²

US $283/Night 7 Nights - US $1,981

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Highly Rated

Hotel

The St. Regis Longboat Key Resort

9.8

Exceptional

(81 Reviews)

1 Bath

US $1,134/Night 7 Nights - US $7,938

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Condo

Longboat Key - Bayport Beach & Tennis Club Condo

2 Bedrooms 2 Baths 6 Guests 1623 ft²

US $226/Night 7 Nights - US $1,582

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Apartment

Island Time Open Sun, July 19th!

10.0

Exceptional

(2 Reviews)

1 Bedroom 1 Bath 4 Guests 333.68 ft²

US $437/Night 7 Nights - US $3,057

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Beachfront Vacation Rental With Full Gulf View

New

Condo

Beachfront Vacation Rental With Full Gulf View

2 Bedrooms 2 Baths 4 Guests

US $154/Night 7 Nights - US $1,079

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Apartment

Top Floor Sunset Paradise Gulf View Unit 501

10.0

Exceptional

(2 Reviews)

1 Bedroom 1 Bath 6 Guests 699.65 ft²

US $418/Night 7 Nights - US $2,926

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Are you ready for a luxury 5-floor penthouse 60 ft from water, 207 reviews

Highly Rated

Condo

Are you ready for a luxury 5-floor penthouse 60 ft from water, 207 reviews

10.0

Exceptional

(208 Reviews)

1 Bedroom 1 Bath 6 Guests 800 ft²

US $493/Night 7 Nights - US $3,451

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LaPlaya 204D Beach-lovers paradise 200 feet of private beach along the turquoise Gulf of Mexico

Apartment

LaPlaya 204D Beach-lovers paradise 200 feet of private beach along the turquoise Gulf of Mexico

10.0

Exceptional

(1 Review)

3 Bedrooms 2 Baths 6 Guests 1743.75 ft²

US $957/Night 7 Nights - US $6,699

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More Top-Rated Resorts in Longboat Key Area

Why Choose Rent By Owner for your Longboat Key Resorts?

What makes our Resorts 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 Resorts

Where are the best neighborhoods to stay in Longboat Key?

Discover the charm of Longboat Key, Florida, by staying in neighborhoods that offer a perfect blend of tranquility and access to beautiful beaches. The northern part of the island provides a more secluded atmosphere ideal for relaxation, while the southern area offers convenient proximity to local amenities and vibrant community events. Whichever neighborhood you choose, you'll enjoy a peaceful retreat with easy access to the scenic coastline and outdoor activities that make Longboat Key, Florida a top destination.

Longbeach Village

In this charming area, you can enjoy a peaceful coastal atmosphere while staying close to the waterfront, making it an ideal choice for those seeking relaxation and scenic views. The neighborhood offers convenient access to local amenities, ensuring a comfortable stay in this idyllic destination.

View 2398+ Rentals in Longbeach Village

Bay Isles

This upscale neighborhood provides a serene setting with lush landscapes and private avenues, perfect for visitors looking for a touch of elegance. Here, you’ll find a tranquil environment that enhances your experience on this beautiful island's region.

View 821+ Rentals in Bay Isles

Best Times to Visit Longboat Key

When should you plan your Resorts stay?

Timing your vacation here can significantly enhance your experience, as the optimal season to visit the region offers pleasant weather and fewer crowds, making it ideal for enjoying the area's renowned resorts booked through RentByOwner.com.

Peak Season Highlights

Spring (March to May)

During spring, you can enjoy warm weather and increased visitor activity, making it an ideal time for beach outings and outdoor activities at this destination.

Average Temperature Daytime: around 78°F to 85°F - Nighttime: around 60°F to 70°F

Winter Holidays (December to February)

The winter months attract travelers seeking a sunny escape, with pleasant temperatures and festive atmosphere, perfect for relaxing at resorts in the region.

Average Temperature Daytime: around 70°F to 75°F - Nighttime: around 55°F to 65°F

Off-Season Highlights

Summer (June to August)

Summertime sees fewer visitors due to higher humidity and occasional rain, providing a more tranquil environment for those looking to relax at resorts without the crowds.

Average Temperature Daytime: around 88°F to 90°F - Nighttime: around 75°F to 78°F

Fall (September to November)

In the fall, the area experiences a slight drop in tourist activity, offering a peaceful setting for enjoying the coastal scenery and resort amenities.

Average Temperature Daytime: around 80°F to 85°F - Nighttime: around 65°F to 70°F

Weekly Weather Forecast for Longboat Key

How to Book Your Longboat Key Resorts

What's our booking process?

Our platform allows you to browse a curated selection of resorts. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

Search Properties

Use our filters to find the right property that fits your needs.

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Longboat Key

More Top-Rated Resorts in Longboat Key Area

Common Resorts Amenities

What amenities can you expect?

Our Resorts 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 shared outdoor pools, perfect for relaxing under the sun.
Take advantage of lush landscaped gardens and well-maintained green spaces surrounding your accommodation.
Make the most of beachfront or oceanfront patios and decks offering stunning views of the bay or Gulf of Mexico.
Utilize outdoor grilling areas and picnic spots for al fresco dining with family and friends.
Benefit from shaded lounging areas, ideal for unwinding in the warm Floridian climate.
Explore walking trails and outdoor recreation zones close to your vacation rental.
Access to tennis courts, volleyball courts, or other sports facilities available for active pursuits outdoors.

Top Attractions Around Longboat Key

What attractions are nearby?

When staying at a resort in this region, you can enjoy a variety of nearby activities such as relaxing on pristine beaches, exploring scenic nature trails, or engaging in water sports like kayaking and paddleboarding, all just moments from your accommodations.

Family Activities

Beachcombing and Sandcastle Building: Explore the pristine sands along the shoreline, where your family can enjoy collecting shells and constructing creative sandcastles.
Outdoor Nature Tours: Discover the region's natural beauty on guided nature walks that highlight local wildlife and unique coastal ecosystems.
Family-Friendly Water Activities: Engage in calm kayaking or paddleboarding sessions suitable for all ages, giving you a fun way to experience the area's clear waters.
Sunset Cruises: Embark on a relaxing boat cruise at dusk to enjoy breathtaking sunset views over the Gulf, perfect for creating lasting family memories.

Adult Activities

Sunset Sailing Tours: Experience the stunning coastline views on a leisurely sailing tour, perfect for enjoying the region's beautiful sunsets and tranquil waters.
Golfing at Longboat Key Club: Play a round of golf at this renowned club featuring championship courses set against scenic waterfront landscapes, ideal for enthusiasts seeking a refined experience.
Beach Relaxation and Water Sports: Unwind on pristine beaches with opportunities for kayaking, paddleboarding, or simply soaking up the sun in this inviting coastal area.
Fishing Excursions: Join guided fishing trips that take you into productive waters where you can catch local species while enjoying the region’s warm climate.

Other Places to Stay in Longboat Key, FL

Longboat Key Travel Tips

How Can You Make the Most of Your Stay?

Explore the beaches: Spend your days relaxing or engaging in water activities along the pristine shoreline to fully embrace the natural beauty of this coastal area.
Visit local dining spots: Discover the region's culinary offerings by trying popular eateries that serve fresh, local seafood and regional specialties.
Plan outdoor excursions: Take advantage of nearby parks and nature reserves for scenic walks, wildlife watching, and outdoor adventures that highlight this destination’s natural landscape.
Utilize local transportation: Use convenient transportation options to easily navigate between your resort and must-see attractions for a stress-free stay in the area.

Transportation Options

Car rentals: Renting a car provides you with flexibility to explore the area at your own pace, making it easy to access nearby attractions and amenities.
Public transportation: Local bus services offer a cost-effective way to get around the region without the need for a personal vehicle.
Taxi and rideshare services: Convenient for short trips or when you prefer a direct route to your resort or dining destinations.
Bicycle rentals: Explore the scenic coastal surroundings and enjoy the fresh air by renting a bicycle, ideal for leisurely rides along designated paths.

Local Customs Options

Respect for the Environment: Visitors are encouraged to preserve the natural beauty of the region by engaging in eco-friendly practices and supporting conservation efforts.
Beach Etiquette: It is customary to adhere to local guidelines, such as cleaning up after yourself and respecting designated swimming and lounging areas.
Greeting Customs: A friendly nod or a warm smile is appreciated when meeting locals or fellow visitors, reflecting the area's welcoming spirit.
Local Dining Practices: When enjoying meals, it’s common to appreciate fresh seafood and follow traditional dining manners that highlight the regional cuisine.

Longboat Key Resorts Frequently Asked Questions

1. What are the top Resorts 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 Resorts in Longboat Key:

2. How many Resorts are available in Longboat Key?

Currently, the total number of properties listed by RBO in 2026 is over 3 in the Longboat Key area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Resorts in Longboat Key. 

3. What is the cancellation policy for resorts in Longboat Key, Florida?

The cancellation policy varies depending on the specific resort you choose. It is recommended to review the listing details or contact the property owner directly through the booking platform for accurate information regarding cancellations and any applicable fees.

4. Are there any special requirements or restrictions when booking a resort in this destination?

Some resorts may have specific requirements or restrictions such as minimum stay periods, age limits, or additional fees. To ensure a smooth booking process, please read the property description carefully or reach out to the owner for clarification.

5. How do I know if a resort in this area is available for my travel dates?

Availability is typically shown on the listing page during your selected travel dates. If you have specific dates in mind, it’s best to check real-time availability and contact the owner if needed to confirm your reservation before completing the booking.

6. What amenities can I expect at the resorts in the region?

Amenities vary by property but often include features like pool access, beachfront views, Wi-Fi, and parking. For detailed information about what’s included, please review the listing’s amenities section or contact the owner directly.

7. Is there a secure way to pay when booking a resort in this destination?

Yes, most listings offer secure payment options through the booking site. It’s advisable to use the platform’s approved payment methods to protect your transaction and ensure your reservation is confirmed seamlessly.