Photo by Monica Ferro

Grassy Key holiday rentals

We found 2,003 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Grassy Key

Showing deals for:30 Oct - 6 Nov

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Why visit Grassy Key

  • Pristine beaches: Grassy Key offers unspoiled sandy stretches perfect for relaxing seaside strolls and sunbathing.
  • Outdoor adventures: Enjoy a range of activities, from exploring local grassy flats to engaging in water sports in these tranquil surroundings.
  • Natural beauty: The island’s scenic charm and lush landscapes provide a refreshing retreat for nature enthusiasts.
  • Family-friendly ambience: Grassy Key is ideal for family holidays with its safe, welcoming environment and recreational offerings.
  • Cosy stays: Choose from a variety of affordable, comfortable accommodations that complement the island’s serene atmosphere.

Popular types of accommodation around Grassy Key

Planning a trip to Grassy Key, Florida, USA? Explore a range of choices including private holiday homes, cosy condos and elegant villas. Enjoy cheap stays and some of the best accommodations, ensuring a comfortable stay. With a focus on search accommodation and holiday rentals, Grassy Key invites you to discover its local attractions, landmarks and experiences that promise a delightful getaway.

  • Private Holiday Homes: The top choice for visitors in Grassy Key, these private escapes offer a cosy and exclusive setting for a memorable break.
  • Condos: A popular option, these well-appointed units provide a modern and comfortable stay in the heart of the locale.
  • Villas: Renowned for their spacious layouts, these elegant retreats offer a touch of luxury in Grassy Key.
  • Cottages: These quaint and charming dwellings deliver a delightful, traditional holiday experience.
  • Apartments: Offering convenience and comfort, these units are a practical choice for a relaxed stay in Grassy Key.**

Top attractions near Grassy Key

Grassy Key, Florida, United States of America offers a delightful escape for beach, outdoor, and family holidays. Enjoy the pristine beach, explore the national or state parks, and savour the island scenery. Ideal for a Florida Keys trip or a Grassy Key adventure, visitors can revel in a variety of outdoor activities and sights unique to the area. Discover the natural beauty and charm that make this destination a true gem for travellers.

  • Sombrero Beach: Enjoy a pristine beach with inviting beach vibes, located 16km from Grassy Key. Ideal for a day by the sea, soaking up the sun and relishing the coastal charm.
  • Long Key State Park: Discover the great outdoors with scenic views, ideal for adventure and outdoor pursuits, situated 14km from Grassy Key. Perfect for a nature walk or a spot of picnicking amidst spectacular landscapes.
  • Little Conch Key: Experience the allure of an island retreat, 6km from Grassy Key, offering both beach and outdoor adventures in a relaxed setting.

Things to do recommended for couples

Grassy Key offers couples the chance to unwind on its serene beaches, indulge in a sunset dinner cruise, or explore the vibrant marine life while snorkelling. Don't miss a romantic stroll through the picturesque surroundings, creating unforgettable memories together in this idyllic paradise.

Things to do recommended for families

Families visiting Grassy Key can explore family-friendly activities, including water sports and nature trails, while enjoying scenic views of the surrounding area. Local eateries offer a taste of authentic flavours, ensuring a memorable and engaging experience for all ages.

Things to do recommended for groups

Discover Grassy Key's charm by cycling through scenic coastal paths and gathering for sunset picnics. Engage in local culinary tours and explore historic sites, offering a balanced blend of relaxation and adventure for your group holiday.

*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

Whether you're travelling as part of a group, with your family, including your pets, or seeking extended stays, ensure you apply the appropriate filters. Here are some Stayz booking tips for you.

  • Traveling to Grassy Key with a group: Consider how many bedrooms you will require, along with amenities such as a fully-equipped kitchen or an outdoor area suitable for a group gathering. Luckily, you can use Stayz to filter for these features and many others.
  • Traveling to Grassy Key with young kids: Traveling with young children can be demanding. You must prioritise their comfort and safety, while ensuring access to age-appropriate facilities, such as a private swimming pool. It is also advisable to consider your closeness to attractions that appeal to families.
  • Taking your pets with you to Grassy Key: For many, a family holiday isn’t complete without their canine companion in tow. If you find yourself in this situation, consider exploring Stayz properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of the family feels perfectly at home.
  • Planning for a long term stay visiting Grassy Key: If you’re in search of holiday rentals offering 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 consider adding features like a parking space, a well-equipped kitchen, or a private pool to your search criteria.

Where to stay near Grassy Key

Grassy Key offers a serene island retreat with pristine beaches and ample outdoor adventures. Enjoy family-friendly excursions and explore the natural beauty of the Florida Keys right here in Grassy Key. From relaxing seaside strolls to discovering the local grassy flats, the village provides an ideal base for a tranquil holiday filled with friendly faces and recreational opportunities.

  • Marathon: Situated within the heart of the Florida Keys, Marathon offers a delightful blend of outdoor activities and family-friendly experiences. As the gateway to Grassy Key, this city is known for its beautiful beaches and vibrant tourist precincts. Visitors can enjoy a variety of water sports, from snorkelling to fishing, or simply relax at one of the local family beaches. The shopping malls and centres add to the charm, providing ample opportunities for unique souvenirs and local crafts. With its stunning coastal scenery and a plethora of recreational options, Marathon is a perfect stop for a memorable holiday.
  • Key Colony Beach: Located a short drive of 8km from Grassy Key, Key Colony Beach is a picturesque island city that epitomises laid-back coastal living. Renowned for its pristine beaches, this destination invites visitors to bask in the sun or partake in various outdoor activities. The recreational areas and shopping options make it a convenient spot for families seeking both relaxation and entertainment. With its scenic waterfront views and tranquil atmosphere, Key Colony Beach provides a serene escape perfect for unwinding and enjoying quality time with loved ones.
  • Duck Key: Just 5km away from Grassy Key, Duck Key is a charming village that captures the essence of island life. Known for its stunning natural beauty, this destination is ideal for families and outdoor enthusiasts alike. Visitors can explore the serene beaches and partake in a range of water activities, from kayaking to paddleboarding. The local shopping areas cater to all your needs, ensuring a fulfilling stay. With its inviting atmosphere and breathtaking landscapes, Duck Key is a delightful spot for creating lasting memories on your holiday.

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 Stayz is simple

Are you hoping to save on your upcoming journey? You might want to consider being flexible with your travel dates, as prices can vary significantly. Additionally, opting for a longer stay often results in substantial savings. To discover the perfect Stayz property that aligns with your budget, utilise our filters to sort by price, location, and type of holiday rental.

Stayz Trips: Planning as easy as it gets

Stayz's innovative Trip Board provides you with a dedicated space to craft new journeys, pick up where you left off, or review and organise your plans. Properties you have previously saved or booked are now conveniently located under Potential, Upcoming, or Current Trips. To access Trip Boards, please visit: https://www.stayz.com.au/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:

  • 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)
  • Curry Hammock State Park (2.5 mi / 4 km)

Frequently asked questions

What is the most popular type of holiday home accommodation in Grassy Key?
Houses are the most popular style of holiday home in Grassy Key, according to our data. Even if you've got a different idea in mind, Stayz 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 home 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 Stayz and the number of guests to view holiday home 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 homes in Grassy Key?
Pack a suitcase and a bone for your canine companion because Grassy Key has 50 holiday homes that throw open their doors to pets. Let your four-legged buddy have fun with the family at one of our pet-friendly holiday homes on Stayz. 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 Stayz, then spend lazy days splishing and splashing in a swimming pool that's only for you.
What are popular home amenities in Grassy Key?
Some of the most popular home 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, Stayz holiday properties have the best amenities for hanging out with the people you cherish the most.
Are there large group holiday homes 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 homes 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 homes in Grassy Key?
Grassy Key has eight one-bedroom homes 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 homes 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 homes 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 Stayz and stay connected on your getaway.
How can I find holiday homes with air conditioning in Grassy Key?
You'll find 50 holiday homes 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 home in Grassy Key?
The age limit can differ across properties on Stayz, 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 home 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 Stayz'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.