Photo by Monica Ferro

Grassy Key holiday lettings

We found 2,001 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Grassy Key

Showing deals for:16 Oct - 23 Oct

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Why visit Grassy Key

  • Stunning Beaches: Grassy Key boasts beautiful sandy shores, ideal for sunbathing and relaxation.
  • Outdoor Adventures: Engage in a variety of activities, including water sports and nature walks amidst lush surroundings.
  • Serene Atmosphere: Enjoy the tranquil vibe, perfect for both family excursions and romantic getaways.
  • Vibrant Marine Life: Discover captivating wildlife and marine experiences, making it a paradise for nature enthusiasts.
  • Diverse Accommodations: Choose from charming vacation homes, cosy condos, and luxurious villas for a perfect stay.

Popular types of accommodation around Grassy Key

Welcome to Grassy Key, Florida, a hidden gem in the heart of the Florida Keys. This tranquil paradise offers stunning coastal views, vibrant marine life, and a variety of outdoor activities. Whether you're looking to unwind in a private vacation home, a cosy condo, or a luxurious villa, Grassy Key has the perfect accommodation for your getaway. Explore the local attractions, from beautiful beaches to captivating wildlife experiences, and make unforgettable memories in this idyllic destination.

  • Houses: The top choice for visitors seeking a homely experience, offering spacious living areas and full amenities.
  • Condos: A popular option providing modern comforts, often with stunning views and shared facilities.
  • Villas: Luxurious accommodations featuring exquisite designs and private outdoor spaces for relaxation.
  • Cottages: Charming and quaint, perfect for those wanting a cosy retreat close to nature.
  • Apartments: Convenient and flexible, ideal for travellers looking for a self-catering stay.**

Top attractions near Grassy Key

Grassy Key, Florida, offers a perfect getaway for beach lovers and outdoor enthusiasts alike. With its stunning beaches, scenic parks, and tranquil island vibes, visitors can indulge in a variety of adventures. Families can enjoy the natural beauty while exploring local attractions that highlight the area's charm and recreational opportunities. Whether you're seeking relaxation or outdoor excitement, Grassy Key promises a delightful vacation experience suited for all ages.

  • Sombrero Beach: A beautiful stretch of sand perfect for sunbathing and swimming, featuring calm waters and picturesque sunsets, ideal for a relaxing day by the sea.
  • Curry Hammock State Park: A natural paradise offering hiking trails, birdwatching, and kayaking, surrounded by stunning scenery and diverse wildlife, perfect for outdoor enthusiasts.
  • Little Conch Key: A tranquil island escape with beautiful beaches and outdoor activities, providing a serene atmosphere for swimming, picnicking, and exploring nature.

Things to do recommended for couples

Grassy Key offers a romantic escape with sunset kayaking through mangroves, intimate beach picnics, and snorkelling adventures in crystal-clear waters. Don't miss a scenic drive along the Overseas Highway, where breathtaking views set the perfect backdrop for a couple's getaway.

Things to do recommended for families

Families visiting Grassy Key can explore the enchanting Dolphin Research Center, where kids can interact with dolphins, and enjoy a day at the beautiful Sombrero Beach, perfect for sandcastle building and swimming in the warm waters of the Florida Keys.

Things to do recommended for groups

Explore the beautiful waters with a group kayaking adventure through the mangroves or indulge in a thrilling day of fishing chartering. Enjoy a sunset cruise for stunning views, or visit the Dolphin Research Center to learn about marine life and engage with these playful creatures.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

When planning your trip, whether you're travelling with a group, as a family, bringing along your pets, or seeking extended stays, it's essential to apply the appropriate filters based on your priorities. Here are some helpful booking tips for Vrbo.

  • Traveling to Grassy Key with a group: Think about how many bedrooms you require, along with features like a fully equipped kitchen or outdoor areas for socialising. Thankfully, you can easily refine your search for all these options and more on Vrbo.
  • Traveling to Grassy Key with young kids: Travelling with young children can present its own set of challenges. It's important to prioritise their comfort and safety, along with ensuring access to suitable amenities like a private swimming pool. Additionally, it would be wise to think about your closeness to family-friendly attractions.
  • Taking your pets with you to Grassy Key: For many families, a holiday isn't truly fulfilling without their furry companion by their side. If that resonates with you, explore Vrbo properties that welcome pets. Most of these 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 that offer discounts for stays of a month or more, you've come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don’t forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Grassy Key

Grassy Key, Florida, offers a delightful island getaway perfect for families and couples alike. With its stunning beaches and lush surroundings, visitors can indulge in outdoor adventures, from water sports to relaxing sunbathing. The friendly atmosphere invites exploration, making it an ideal destination for family-friendly excursions and romantic retreats. Immerse yourself in the natural beauty of the Florida Keys as you create unforgettable memories in this serene coastal paradise.

  • Marathon: Marathon is a vibrant city that encompasses Grassy Key, offering a delightful blend of beach and outdoor experiences perfect for families. The city boasts a variety of accommodations, from luxurious resorts to quaint motels, ensuring a comfortable stay. Visitors can enjoy the popular family beach and explore the bustling tourist precinct filled with shops and dining options. The scenic beauty of Marathon, with its stunning beaches and waterfront activities, makes it an ideal destination for sun seekers and adventure enthusiasts alike.
  • Key Colony Beach: Situated a mere 8km from Grassy Key, Key Colony Beach is a picturesque island city that invites visitors to unwind in a serene environment. This community is renowned for its beautiful beaches and outdoor recreational areas, perfect for family outings. The local shopping mall centre provides convenient access to various shops and eateries, enhancing the overall travel experience. Key Colony Beach offers a tranquil escape for those looking to relax on the sandy shores or engage in water sports.
  • Duck Key: Only 5km from Grassy Key, Duck Key is a charming village that captures the essence of island living. With a focus on outdoor and family-friendly activities, visitors can explore the lovely beaches and vibrant community. Duck Key is home to several resorts and shopping areas, making it an accessible destination for tourists. Its idyllic setting and inviting atmosphere provide a perfect backdrop for relaxation, family bonding, and enjoying the beautiful Florida Keys lifestyle.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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 next holiday? Being flexible with your travel dates can be a great way to take advantage of price fluctuations. Additionally, opting for a longer stay often results in significant savings. To discover the perfect Vrbo property that fits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board provides a convenient platform for you to create new trips, manage your plans, or review and organise your bookings. Your saved or booked properties are thoughtfully categorised into Potential, Upcoming, or Current Trips. To explore the Trip Boards, please 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:

  • Sombrero Beach (9.7 mi / 15.6 km)
  • Curry Hammock State Park (2.5 mi / 4 km)
  • Coco Plum Beach (3.8 mi / 6.1 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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