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Grassy Key holiday rentals

We found 1,973 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Grassy Key

Showing deals for:11 Dec - 18 Dec

Family-style dining space with open concept for effortless entertaining.
Heated waterfront pool with loungers, tropical landscaping, and canal view.
Open, fully equipped kitchen perfect for preparing family meals together.
Bright two-story living space with soaring ceilings and modern design.
Exceptional
(134 reviews)

Salty Anglers: Waterfront Heated Pool, Dock & Walk to Sombrero Beach in Marathon

Marathon

10% off
AU$5,258
for 7 nights, 1 home
AU$751 per night
includes taxes & fees
Salty Anglers: Waterfront Heated Pool, Dock & Walk to Sombrero Beach in Marathon
View from the balcony
Property grounds
Exterior
View from the kitchen into the dining and living room
Exceptional
(34 reviews)

New Paradise On Sombrero Beach

Marathon

8% off
AU$5,769
for 7 nights, 1 villa
AU$824 per night
includes taxes & fees
New Paradise On Sombrero Beach
Private kitchen
Exterior
Living area
Living area
Exceptional
(45 reviews)

Fisherman Paradise, Dock, Pool , Ice Machine, Jacuzzi.

Marathon

7% off
AU$7,955
for 7 nights, 1 home
AU$1,136 per night
includes taxes & fees
Fisherman Paradise, Dock, Pool , Ice Machine, Jacuzzi.
Pool
Exterior
View from the lanai. 🐠🌴☀️🎣
Roomy kitchen
Exceptional
(112 reviews)

Beautiful Canal front w/ dock - private pool -4/3~walk to beach~Outdoor smart tv

Marathon

8% off
AU$6,448
for 7 nights, 1 home
AU$921 per night
includes taxes & fees
Beautiful Canal front w/ dock - private pool -4/3~walk to beach~Outdoor smart tv
Marina
Property grounds
Dining
Interior
Exceptional
(54 reviews)

Convenient central Marathon location, canal view.

Marathon

7% off
AU$1,856
for 7 nights, 1 home
AU$265 per night
includes taxes & fees
Convenient central Marathon location, canal view.
Dining
Exterior
Marina
Private kitchen
Exceptional
(12 reviews)

Sleeps 10 - Private house with 110’ of Deep Water Dockage, Pool, Hot Tub & more!

Marathon

9% off
AU$25,852
for 7 nights, 1 home
AU$3,693 per night
includes taxes & fees
Sleeps 10 - Private house with 110’ of Deep Water Dockage, Pool, Hot Tub & more!
Room
Exterior detail
Interior
Pool
Very good
(6 reviews)

New Keys Cabins. Family sized cabins with full kitchens,

Marathon

8% off
AU$3,403
for 7 nights, 1 cabin
AU$486 per night
includes taxes & fees
New Keys Cabins. Family sized cabins with full kitchens,
A little bamboo grove on the way to the canal out back
Pool
Relax poolside with a cold drink and a hot book
New kitchen opens up to living and dining room
Exceptional
(79 reviews)

Sombrero Beach Home - Heated Pool, Kayaks, Private Road

Marathon

8% off
AU$6,571
for 7 nights, 1 home
AU$939 per night
includes taxes & fees
Sombrero Beach Home - Heated Pool, Kayaks, Private Road
Kitchen Cabinets
Pool/Spa
Kitchen Island
Fire pit, boat lift, fishing table, cabana, outside chairs
Exceptional
(5 reviews)

BEST House in Marathon With Ocean View!

Marathon

7% off
AU$8,459
for 7 nights, 1 home
AU$1,208 per night
includes taxes & fees
BEST House in Marathon With Ocean View!
Enjoy a morning coffee out on your private balcony.
A common walkway leads to Conch Cottage: Vacation vibes on Harbor Village Drive!
Kick back, read, play board games & watch TV in the well-appointed living area.
Conch Cottage from above, with so much more outdoor space than our neighbors.
Wonderful
(9 reviews)

Hawks Cay Island Retreat - Duck Key - Pool & Patio

Marathon

8% off
AU$5,609
for 7 nights, 1 villa
AU$801 per night
includes taxes & fees
Hawks Cay Island Retreat - Duck Key - Pool & Patio
Living area
Outdoor dining
Private kitchen
Dining
Exceptional
(32 reviews)

Open Ocean View, Private Hot Tub, Ice Machine, Moor 26' Boat!

Marathon

7% off
AU$5,109
for 7 nights, 1 home
AU$730 per night
includes taxes & fees
Open Ocean View, Private Hot Tub, Ice Machine, Moor 26' Boat!
Its not a Mirage...its Mirage Manor
Pool
Huge Porch View 2
Interior
Exceptional
(38 reviews)

Marathon 3BR on 55' Canal Boat Dock w Pool Spa Hot Tub Free pool heat bay side

Marathon

8% off
AU$6,309
for 7 nights, 1 home
AU$901 per night
includes taxes & fees
Marathon 3BR on 55' Canal Boat Dock w Pool Spa Hot Tub Free pool heat bay side
Exterior
Marina
Pool
Sectional couch in living room
Exceptional
(60 reviews)

Marlin House 52: Gated Luxury Villa w/ Dockage, Sunset Views and Pool

Marathon

7% off
AU$4,635
for 7 nights, 1 villa
AU$662 per night
includes taxes & fees
Marlin House 52: Gated Luxury Villa w/ Dockage, Sunset Views and Pool
Property grounds
Pool
Interior
Property grounds
Exceptional
(16 reviews)

Isla Marlin 28: Palm lined luxury villa w/dockage and sunset views

Marathon

8% off
AU$4,724
for 7 nights, 1 villa
AU$675 per night
includes taxes & fees
Isla Marlin 28: Palm lined luxury villa w/dockage and sunset views
Second bedroom
Room
Private kitchen
Interior
Wonderful
(21 reviews)

Charming 2beds 2 baths w/pool 10 mins from the beach!

Marathon

7% off
AU$2,537
for 7 nights, 1 home
AU$362 per night
includes taxes & fees
Charming 2beds 2 baths w/pool 10 mins from the beach!
A complete kitchen with everything you will need to cook family meals at home!
Paradise found!
Your arrival
Relax and watch the kiddos in the pool
Exceptional
(43 reviews)

Welcome to Paradise! Private Pool, 40' Dock, Great Location

Key Colony Beach

8% off
AU$5,931
for 7 nights, 1 home
AU$847 per night
includes taxes & fees
Welcome to Paradise! Private Pool, 40' Dock, Great Location
Property grounds
Pool
Property grounds
Private kitchen
Exceptional
(11 reviews)

Key Colony Beach Home Casa Sunny Sea Key Colony Beach, Fl Keys

Key Colony Beach

8% off
AU$5,311
for 7 nights, 1 home
AU$759 per night
includes taxes & fees
Key Colony Beach Home Casa Sunny Sea Key Colony Beach, Fl Keys
Interior
Terrace/patio
Dining
Private kitchen
Exceptional
(16 reviews)

15% off promo to 12/23-Updated 3/3, Cabana Club Pool Membership, Dock, Tiki Hut

Key Colony Beach

11% off
AU$4,415
for 7 nights, 1 home
AU$631 per night
includes taxes & fees
15% off promo to 12/23-Updated 3/3, Cabana Club Pool Membership, Dock, Tiki Hut
Living area
Dining
Pool
Room
Exceptional
(36 reviews)

Harbor Hideaway - 3bed,2bath,50' dock, heated pool, tiki with all the amenities.

Marathon

8% off
AU$6,714
for 7 nights, 1 home
AU$959 per night
includes taxes & fees
Harbor Hideaway - 3bed,2bath,50' dock, heated pool, tiki with all the amenities.
Pull out sofa bed w/ comfortable  mattress. Property #2178313 for more reviews
Pool
Over the rainbow
Flat screen Smart TV in living room with HBO & Showtime anytime
Exceptional
(41 reviews)

Tropical Paradise 🏝! POOL, Hot Tub, Dock, FREE Ice, Kayaks, Paddles, Bikes!

Key Colony Beach

8% off
AU$4,005
for 7 nights, 1 home
AU$572 per night
includes taxes & fees
Tropical Paradise 🏝! POOL, Hot Tub, Dock, FREE Ice, Kayaks, Paddles, Bikes!
Take a walk to Sunset Park
Relax on a bench or at a table
Facilities on site
Grab a chair... We have a perfect place to enjoy your morning coffee
Dock has a lower section also
Our dock is a perfect place to enjoy your favorite evening beverage on
Exceptional
(94 reviews)

KCB-access Private Cabana Club, Dock on Canal, PET Friendly, Pickle ball courts

Key Colony Beach

9% off
AU$2,143
for 7 nights, 1 home
AU$306 per night
includes taxes & fees
KCB-access Private Cabana Club, Dock on Canal, PET Friendly, Pickle ball courts
Exterior
Pool
Room
Property grounds
Exceptional
(15 reviews)

Charming 3-Bedroom Villa Centrally Located in the Florida Keys

Marathon

7% off
AU$5,052
for 7 nights, 1 villa
AU$722 per night
includes taxes & fees
Charming 3-Bedroom Villa Centrally Located in the Florida Keys
Privacy bamboo fence
Bay views from the bar 🌘, Book your Holiday & 2024 dates now!
Enjoy 100 plus channels and YouTube on 55-inch Samsung smart TV, watch Netflix
Cozy & comfy, perfect for family & friends time🌴
Exceptional
(136 reviews)

CLEAR water views @Tiki haven! Quick ocean access, Pool, HotTub, FUN! FREE ICE!

Key Colony Beach

8% off
AU$4,527
for 7 nights, 1 home
AU$647 per night
includes taxes & fees
CLEAR water views @Tiki haven! Quick ocean access, Pool, HotTub, FUN! FREE ICE!
Marina
Property grounds
Living area
Exterior
Exceptional
(203 reviews)

Finest location in Coral Lagoon. End unit with bay views and boat slip!

Marathon

8% off
AU$6,760
for 7 nights, 1 home
AU$966 per night
includes taxes & fees
Finest location in Coral Lagoon. End unit with bay views and boat slip!
  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

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:

  • 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 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.

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