Grassy Key holiday lettings

We found 1,955 holiday rentals — enter your dates for availability

Why visit Grassy Key

  • Stunning beaches: Relax on picturesque beaches and soak up the sun in the beautiful Florida Keys.
  • Outdoor activities: Explore the scenic Grassy Key Trail and enjoy a variety of recreational activities.
  • Dolphin experiences: Engage with dolphins for a memorable and unique wildlife encounter.
  • Florida Keys Overseas Heritage Trail: Perfect for adventure enthusiasts wanting to cycle or walk through stunning landscapes.
  • Diverse accommodation options: Choose from charming cottages, condos, luxury villas, and RV parks.

Popular types of accommodation around Grassy Key

Vrbo offers a diverse selection of accommodation in Grassy Key, catering to every traveller's needs. Whether you're seeking the comfort of private holiday cottages, the convenience of condos, or the luxury of villas, you’ll find the perfect fit. Popular options include Grassy Key hotels and the charming Grassy Flats Resort, along with house rentals and an RV park for those looking to embrace the outdoors. Discover your ideal getaway today!

  • Houses: The top choice for visitors in Grassy Key, these homes offer spacious and comfortable living, perfect for families or groups seeking a homely atmosphere.
  • Condos: A popular option, condos provide a blend of convenience and luxury, often featuring stunning views and shared amenities.
  • Villas: Stylish and spacious, villas are an ideal choice for those looking for a touch of elegance during their stay.
  • Cottages: Charming and quaint, cottages offer a cosy retreat, perfect for couples or solo travellers wanting a peaceful getaway.
  • Apartments: A practical choice for many, apartments provide essential comforts and are conveniently located near local attractions.**

Top attractions near Grassy Key

Grassy Key is ideal for outdoor and family holidays, offering stunning beaches and national parks to explore. Visitors can enjoy various attractions, including dolphin experiences and the Florida Keys Overseas Heritage Trail, perfect for adventure enthusiasts. Don’t miss the picturesque Grassy Key Trail for memorable photos. Whether you're seeking relaxation or adventure, Grassy Key has something for everyone.

  • Sombrero Beach: A beautiful sandy haven located 6.2km from Grassy Key, Sombrero Beach offers a relaxed atmosphere perfect for sunbathing and swimming. Enjoy stunning sunsets and beach vibes while taking in the crystal-clear waters and palm trees swaying in the breeze.
  • Curry Hammock State Park: Situated 1.2km from Grassy Key, this state park is an outdoor enthusiast's paradise. With diverse wildlife, scenic views, and numerous trails, visitors can indulge in kayaking, hiking, and birdwatching amidst the park's natural beauty.
  • Crawl Key: Just 1.2km away, this charming island features gorgeous beaches ideal for outdoor activities. Explore the coastline, relax on the sandy shores, or enjoy water sports in the warm, inviting waters, all while soaking in the laid-back beach vibes.

Things to do recommended for couples

Planning a romantic getaway in Grassy Key? Indulge in the luxurious ambiance at the Florida Keys Country Club, just 5.6km away. For adventure enthusiasts, Pigeon Key offers thrilling water sports and outdoor fun, located 8.1km from your base. Perfect for couples seeking both relaxation and excitement!

Things to do recommended for families

Families visiting Grassy Key can delight in the Dolphin Research Center, where they can interact with dolphins, and explore the beautiful beaches for swimming and sunbathing. Additionally, nearby, the Florida Keys Aquarium Encounters offers hands-on marine life experiences suitable for all ages.

Things to do recommended for groups

Experience the thrill of water sports at Keys Cable Park, located in Grassy Key. Gather your friends for an exhilarating day filled with adventure vibes, perfect for making lasting memories together.

What do I need to keep in mind when booking a vacation around Grassy Key

If you’re travelling with a group, family, pets, or seeking longer stays, be sure to filter according to your key priorities. Here are some helpful booking tips for Vrbo.

  • Traveling to Grassy Key with a group: Think about how many bedrooms you'll require, as well as features like a complete kitchen or outdoor area for group gatherings. Thankfully, you can refine your search for all these options and more on Vrbo.
  • Traveling to Grassy Key with young kids: Travelling with young children can be a bit demanding. It's essential to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, you might want to think about how close you are to attractions that are friendly for families.
  • Taking your pets with you to Grassy Key: For many, a family holiday wouldn’t be the same without their furry companion. If this resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Grassy Key: If you’re seeking holiday rentals with discounts for stays of a month or more, you’ve come to the right spot. By using the appropriate filter, you can effortlessly discover and save on monthly rentals. Don’t forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay near Grassy Key

Grassy Key offers a delightful escape into the beauty of the Florida Keys, perfect for outdoor enthusiasts and families alike. Explore the scenic Grassy Key Trail, unwind on the picturesque beaches, and enjoy the friendly atmosphere that surrounds this charming village. With its stunning lagoon and abundance of recreational activities, Grassy Key promises a relaxing holiday filled with memorable excursions and warm hospitality.

  • Marathon: Located 5.6km from Grassy Key, Marathon is a vibrant city known for its excellent outdoor and family-friendly experiences. This bustling destination boasts beautiful beaches and a variety of resorts, making it ideal for relaxation and recreation. Explore the local shopping mall and vibrant shopping areas, where you can find unique souvenirs and delightful dining options. Notable attractions include the stunning family beach and the lively tourist precinct, ensuring visitors have a wealth of activities to choose from.
  • Key Colony Beach: Situated 3.1km from Grassy Key, Key Colony Beach is a charming island city that emphasises its natural beauty. This locale is perfect for families and beach enthusiasts, offering a mix of recreational areas and shopping opportunities. Spend your days lounging on the pristine beaches or engaging in various outdoor activities. The area is renowned for its family beach and picturesque island scenery, promising a tranquil yet engaging getaway for all ages.
  • Duck Key: Just 1.9km from Grassy Key, Duck Key is a lovely village that captures the essence of island life. Known for its stunning outdoor spaces and family-oriented experiences, Duck Key offers an array of resorts and shopping areas. Visitors can revel in the beauty of the local beaches, with family-friendly options available. The inviting atmosphere and natural charm of this village make it a perfect spot for relaxation and exploration.

Best time to go to Grassy Key

If you're planning a trip to Grassy Key, Marathon, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs in February to March and July, while off-peak times, like September to November tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January70.9°F (21.6°C)No Rain (Dry)Mostly SunnyAverageSlightly Low
February72.1°F (22.3°C)No Rain (Dry)Mostly SunnyModerately HighAverage
March73.2°F (22.9°C)No Rain (Dry)Mostly SunnyModerately HighAverage
April76.8°F (24.9°C)No Rain (Dry)Mostly SunnyAverageAverage
May79.3°F (26.3°C)Light RainMostly SunnyAverageAverage
June82.6°F (28.1°C)Light RainMostly SunnyAverageSlightly High
July84.0°F (28.9°C)Light RainMostly SunnyModerately HighSlightly High
August84.4°F (29.1°C)Light RainMostly SunnyAverageAverage
September83.5°F (28.6°C)Light RainMostly SunnyModerately LowSlightly Low
October80.6°F (27.0°C)Light RainMostly SunnyModerately LowSlightly Low
November76.5°F (24.7°C)Light RainMostly SunnyModerately LowAverage
December73.6°F (23.1°C)No Rain (Dry)Mostly SunnyAverageSlightly High

Booking with Vrbo is a breeze

Are you hoping to save on your upcoming adventure? Being flexible with your travel dates can be beneficial, as prices often fluctuate. Additionally, you can enjoy considerable savings by opting for a longer stay. To discover a Vrbo property that suits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo’s cutting-edge Trip Board offers you a dedicated space to plan new journeys, pick up where you last left off, and manage your travel arrangements. You can easily access properties you have previously saved or booked, now conveniently organised under Potential, Upcoming, or Current Trips. To explore the Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Delight in the beachside landscape of Grassy Key

The beaches and surrounding scenery provide a peaceful ambience to your holiday home in Grassy Key. This city is well-known for its dolphin watching and seafood restaurants. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Exploring the beaches and other natural features in Grassy Key

Travellers enjoy Grassy Key for its seaside and sunsets. 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 Grassy Key. Here are some of the area’s most stunning sights, all within 30 miles (48.2 km) of the city centre:

  • Curry Hammock State Park (2.5 mi / 4 km)
  • Coco Plum Beach (3.8 mi / 6.1 km)
  • Sombrero Beach (9.7 mi / 15.6 km)
  • Vaca Key (11.3 mi / 18.1 km)
  • Fiesta Key (11.4 mi / 18.4 km)
  • Anne's Beach (14.6 mi / 23.5 km)

Frequently asked questions

What is the most popular type of holiday rental accommodation in Grassy Key?
Houses are the most popular style of holiday rental in Grassy Key, according to our data. Even if you've got a different idea in mind, Vrbo has holiday homes in all sizes and shapes. Take a look at our options to find your perfect match.
How much does it cost to rent a holiday rental in Grassy Key?
The average price for a holiday home in Grassy Key can vary based on factors such as property type, length of stay and season. Whether you're thinking about a sprawling villa with room to move around or a comfy cabin just enough for two, just enter your travel dates to discover some great-value stays.
How much does it cost to rent a beach house in Grassy Key?
Prices for beach houses in Grassy Key vary depending on the type and size of the property and when you plan to travel. Simply enter your travel dates into Vrbo and the number of guests to view holiday rental options and prices. From there you can use the filters to refine your search results by ratings, nearby activities and more.
Are there pet-friendly holiday rentals in Grassy Key?
Pack a suitcase and a bone for your canine companion because Grassy Key has 50 holiday rentals that throw open their doors to pets. Let your four-legged buddy have fun with the family at one of our pet-friendly holiday rentals on Vrbo. Simply enter your destination and travel dates, then check our "Pets allowed" filter box.
Can I rent a house with a pool in Grassy Key?
Add a whole new level of fun to your getaway by staying in one of the 35 houses with a private pool in Grassy Key. Use our search filter to find properties with pools on Vrbo, then spend lazy days splishing and splashing in a swimming pool that's only for you.
What are popular rental amenities in Grassy Key?
Some of the most popular rental amenities people look for in Grassy Key are a nearby waterfront, an ocean view and a garden. Whether you're holidaying with friends, family or even pets, Vrbo holiday properties have the best amenities for hanging out with the people you cherish the most.
Are there large group holiday rentals in Grassy Key?
You'll discover eight holiday properties in Grassy Key that can accommodate a group of 10 or more guests. Whether you're organising a get-together with extended family or an event like a birthday party, there's enough space to get your favourite people together under the same roof.
Are there holiday rentals in Grassy Key that welcome kids?
Grassy Key has 50 family-friendly holiday homes. And booking a stay that welcomes little ones is super easy with our "Properties good for families" filter. On top of having the whole place to yourselves, you'll get perks and conveniences such as dining rooms, pools and kitchens.
What are the top attractions for families in Grassy Key?
You'll find lots of awesome things to see and do with the family in Grassy Key, such as:

  • Coco Plum Beach
  • Florida Keys Aquarium Encounters
  • Crane Point Museum and Nature Centre

Are there one-bedroom holiday rentals in Grassy Key?
Grassy Key has eight one-bedroom rentals available. Typically located in sought-after areas thanks to their smaller size, a one-bedroom holiday property is ideal if you're getting away with a pal or your partner. And with comforts like air conditioning and more privacy than a standard hotel, you'll be able to kick back and relax while exploring this amazing destination.
Can I find two-bedroom holiday rentals in Grassy Key?
Gather your loved ones and enjoy total privacy and comfort in one of the seven two-bedroom holiday homes Grassy Key has to offer.
Are there holiday rentals with WiFi in Grassy Key?
Whether you'd like to keep up with world events, reply to emails or surf your social networks, there are 18 holiday homes with WiFi in Grassy Key. Check the "WiFi" box when searching on Vrbo and stay connected on your getaway.
How can I find holiday rentals with air conditioning in Grassy Key?
You'll find 50 holiday rentals with air conditioning in Grassy Key offering that gentle, cool breeze and extra comfort level. Simply enter your preferred dates of travel and then use our handy filters to find properties with air conditioning.
How old do you have to be to rent a holiday rental in Grassy Key?
The age limit can differ across properties on Vrbo, so be sure to check the rules of the holiday home in Grassy Key you want to book. But typically, it's 16, 18 or 21.
How long can I rent a holiday rental in Grassy Key for?
It's down to the Grassy Key property. To browse a list of options offering extended stays, just enter your dates and guest number into Vrbo's search page. Look forward to having the entire property to yourself, along with home comforts like air conditioning, a kitchen and a yard where your little ones can play. Be on the lookout for any long-term stays that offer discounted weekly or monthly prices.

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