Photo by Monica Ferro

Grassy Key vacation rentals

We found 1,994 vacation rentals — enter your dates for availability

Welcome to Grassy Key, where stunning sandy beaches meet vibrant marine life in a laid-back paradise. This idyllic destination invites you to bask in the sun, snorkel through colorful reefs, and explore the natural wonders of nearby parks. With charming vacation rentals ranging from cozy cottages to beachfront villas, groups and families can enjoy the comfort and convenience of home while creating unforgettable memories together in this welcoming community.

Holiday rentals with weekly discounts - Grassy Key

Showing deals for:Nov 6 - Nov 13

Exterior
Exterior
Exterior
Exterior
Exceptional
(43 reviews)

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

Marathon

8% off
$755
$5,286 for 7 nights
All fees included
Fisherman Paradise, Dock, Pool , Ice Machine, Jacuzzi.
Downstairs master bedroom
Exterior
Master bedroom
King size bed
Exceptional
(111 reviews)

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

Marathon

8% off
$618
$4,329 for 7 nights
All fees included
Beautiful Canal front w/ dock - private pool -4/3~walk to beach~Outdoor smart tv
Spacious living room with plush seating, flat-screen TV, and natural light.
Charming canal-side home with private dock and lush tropical landscaping.
Private deep-water dock with fast ocean access for boating and fishing.
Open, fully equipped kitchen perfect for preparing family meals together.
Exceptional
(132 reviews)

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

Marathon

10% off
$514
$3,595 for 7 nights
All fees included
Salty Anglers: Waterfront Heated Pool, Dock & Walk to Sombrero Beach in Marathon
Full Equipped Kitchen
Exterior
Villa exterior
Kitchen sitting area
Exceptional
(33 reviews)

New Paradise On Sombrero Beach

Marathon

8% off
$548
$3,835 for 7 nights
All fees included
New Paradise On Sombrero Beach
Large sectional sofa has room for everyone
Enjoy relaxing in and around the pool, overlooking a secluded canal
New kitchen opens up to living and dining room
New kitchen is a pleasure to cook in or just hang out on the bar stools
Exceptional
(78 reviews)

Sombrero Beach Home - Heated Pool, Kayaks, Private Road

Marathon

8% off
$597
$4,176 for 7 nights
All fees included
Sombrero Beach Home - Heated Pool, Kayaks, Private Road
Interior
Exterior
Exterior
Exterior detail
Very Good
(6 reviews)

New Keys Cabins. Family sized cabins with full kitchens,

Marathon

8% off
$325
$2,274 for 7 nights
All fees included
New Keys Cabins. Family sized cabins with full kitchens,
Gated Accessible parking
Paradise Pool/Heat Spa
Front of House
Garge with washer/dryer
Exceptional
(5 reviews)

BEST House in Marathon With Ocean View!

Marathon

8% off
$801
$5,610 for 7 nights
All fees included
BEST House in Marathon With Ocean View!
Pool
Welcome to Paradise!!
Sunsets from the patio 😍
Manatees are frequent visitors to the dock!
Exceptional
(43 reviews)

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

Key Colony Beach

8% off
$469
$3,281 for 7 nights
All fees included
Welcome to Paradise! Private Pool, 40' Dock, Great Location
Pool
Dining
Dining
Property grounds
Exceptional
(36 reviews)

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

Marathon

8% off
$612
$4,286 for 7 nights
All fees included
Harbor Hideaway - 3bed,2bath,50' dock, heated pool, tiki with all the amenities.
Dining
Living area
Dining
Dining
Exceptional
(54 reviews)

Convenient central Marathon location, canal view.

Marathon

8% off
$192
$1,346 for 7 nights
All fees included
Convenient central Marathon location, canal view.
Living room opens to the Florida Bay
Beach
Kitchen
Living room
Exceptional
(72 reviews)

Stay where you play, On the water w/Boat dock & Trailer parking. Pet friendly!

Long Key

8% off
$302
$2,111 for 7 nights
All fees included
Stay where you play, On the water w/Boat dock & Trailer parking. Pet friendly!
Uncluttered kitchen features granite countertops & stainless-steel appliances.
Welcome to the Conch Cottage at Hawks Cay Resort in Duck Key, Florida.
Ultra-private resort-style living. Tropical gardens flank the plunge pool.
A quintessential island retreat w/ private entrance leading to big back patio.
Wonderful
(9 reviews)

Hawks Cay Island Retreat - Duck Key - Pool & Patio

Marathon

8% off
$446
$3,122 for 7 nights
All fees included
Hawks Cay Island Retreat - Duck Key - Pool & Patio
Aerial view
Property grounds
Marina
Pool
Exceptional
(15 reviews)

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

Marathon

8% off
$454
$3,177 for 7 nights
All fees included
Isla Marlin 28: Palm lined luxury villa w/dockage and sunset views
Exterior
Exterior
Exterior
Exterior
Exceptional
(10 reviews)

Luxurious 3-bedroom home with Pool and Dock in Key Colony Beach

Key Colony Beach

7% off
$649
$4,542 for 7 nights
All fees included
Luxurious 3-bedroom home with Pool and Dock in Key Colony Beach
Outdoor dining
Gorgeous sunsets on the large 2nd-floor balcony
2nd-floor fully stocked gourmet kitchen with stainless steel Bosch appliances
Living area
Exceptional
(45 reviews)

FALL & WINTER SPECIALS! 5 Bdrm 5 Bath,Elevator, Private Pool,Dock, Walk to Beach

Marathon

8% off
$869
$6,083 for 7 nights
All fees included
FALL & WINTER SPECIALS! 5 Bdrm 5 Bath,Elevator, Private Pool,Dock, Walk to Beach
Interior
Interior
Room
Living area
Wonderful
(21 reviews)

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

Marathon

8% off
$246
$1,722 for 7 nights
All fees included
Charming 2beds 2 baths w/pool 10 mins from the beach!
Terrace/patio
Cabana Club Pool
Canal View- Dock 37’ in length
Terrace/patio
Exceptional
(16 reviews)

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

Key Colony Beach

12% off
$423
$2,964 for 7 nights
All fees included
Updated 3/3, Cabana Club Pool Membership, Dock, Tiki Hut 15% off promo to 12/23
Beach
Living area
Private kitchen
Pool
Exceptional
(21 reviews)

Salty Air Retreat. 2 Bedroom 1 Bathroom Half Duplex. Dockside.

Marathon

8% off
$374
$2,619 for 7 nights
All fees included
Salty Air Retreat. 2 Bedroom 1 Bathroom Half Duplex. Dockside.
Kitchen with new Samsung stainless steel 4-door refrigerator w/ ice maker
Tiki hut vibes....Relax and unwind here 2/2 is Prop #2178313 & 1/1 is #3396030
Pool, Hot Tub, Tiki, Outdoor cooking, Grill, griddle, Ice! Book this 1/1 or both
Pull out sofa bed w/ comfortable  mattress. Property #2178313 for more reviews
Exceptional
(38 reviews)

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

Key Colony Beach

7% off
$295
$2,065 for 7 nights
All fees included
Tropical Paradise 🏝! POOL, Hot Tub, Dock, FREE Ice, Kayaks, Paddles, Bikes!
A very comfortable pull out (Brand new)
Best views duck key has to offer
Fully redone villa
Exterior
Exceptional
(29 reviews)

Majestic Marina View- 2/2.5 townhome looking over Hawks Cay Marina.

Marathon

8% off
$356
$2,495 for 7 nights
All fees included
Majestic Marina View- 2/2.5 townhome looking over Hawks Cay Marina.
Living area
Outdoor dining
Living area
Living area
Exceptional
(97 reviews)

Razz's Retreat at KCB!

Key Colony Beach

7% off
$268
$1,873 for 7 nights
All fees included
Razz's Retreat at KCB!
Gorgeous sunset out front 🏠
Wake up to this everyday 🌞 while you're on vacay. Watch the sunrise w/ coffee
Night cap... guests enjoying a relaxing massage in hot tub!
Lighted dock, underwater lighting for night time fishing 🎣.  Fun on the back!
Exceptional
(135 reviews)

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

Key Colony Beach

8% off
$373
$2,614 for 7 nights
All fees included
CLEAR water views @Tiki haven! Quick ocean access, Pool, HotTub, FUN! FREE ICE!
Room
Living area
Pool
Bathroom
Exceptional
(8 reviews)

Gated Villa w/ Private Pool, 70" TV, Patio, Carport & Fast Wifi

Marathon

8% off
$623
$4,359 for 7 nights
All fees included
Gated Villa w/ Private Pool, 70" TV, Patio, Carport & Fast Wifi
Interior
Living area
Living area
Living area
Exceptional
(25 reviews)

Key Colony Home with Dock and Cabana Club Access- Pets Welcomed

Key Colony Beach

7% off
$249
$1,741 for 7 nights
All fees included
Key Colony Home with Dock and Cabana Club Access- Pets Welcomed
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • All the privacy of home

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

    More space, more privacy, more amenities — more value
  • A place for everyone

    We stand for diversity, inclusion and families everywhere.
    Learn more

Find out more about Grassy Key

Why visit Grassy Key

  • Stunning Beaches: Grassy Key boasts beautiful sandy shores perfect for sunbathing and relaxation.
  • Outdoor Adventures: Engage in a variety of activities such as snorkeling, kayaking, and exploring nearby national parks.
  • Charming Accommodations: Choose from a range of vacation rentals including cozy cottages and beachfront villas for a homey experience.
  • Vibrant Marine Life: Discover incredible snorkeling spots teeming with colorful reefs and diverse aquatic species.
  • Welcoming Atmosphere: Enjoy the friendly local community and laid-back vibe that enhances your vacation experience.

Popular types of accommodation around Grassy Key

Explore the charm of Grassy Key with a variety of vacation rentals that cater to every traveler’s needs. Choose from houses, condos, or villas, each offering unique amenities. Popular options include Grassy Flats Resort and other private beach FL vacation rentals. Whether you're seeking a relaxing getaway or an adventurous escape, Grassy Key vacation rentals provide the perfect base for your unforgettable experience.

  • Houses: The top choice for visitors to Grassy Key, these homes offer spacious accommodations perfect for families or groups seeking privacy and comfort.
  • Condos: A popular option for travelers, condos provide amenities like pools and ocean views, making them ideal for a relaxing getaway.
  • Villas: These luxurious properties boast elegant designs and ample space, perfect for those looking to indulge during their stay.
  • Cottages: Charming and cozy, cottages in Grassy Key are great for couples or small families wanting a quaint retreat.
  • Apartments: Convenient and often centrally located, apartments are a practical choice for travelers wanting easy access to local attractions.**

Top attractions near Grassy Key

Grassy Key is an ideal destination for beach lovers and families seeking outdoor adventures. Visitors can explore stunning beaches, vibrant islands, and nearby national and state parks. With a variety of attractions catering to outdoor enthusiasts and families alike, Grassy Key promises an unforgettable vacation experience filled with sun, sand, and fun activities for all ages.

  • Curry Hammock State Park: Located 2 miles from Grassy Key, this park offers stunning scenery and a variety of outdoor activities. Enjoy hiking, bird watching, and exploring the unique coastal ecosystems, all while soaking in the natural beauty of the Florida Keys.
  • Coco Plum Beach: Situated 4 miles away, this serene beach is perfect for sunbathing and swimming. With its soft sands and tranquil waters, it's an ideal spot to relax and enjoy the picturesque sunset.
  • Little Conch Key: Just 4 miles from Grassy Key, this charming island features beautiful beaches and outdoor activities. Explore the coastline, go fishing, or simply unwind in nature’s embrace.

Things to do recommended for couples

For a romantic getaway in Grassy Key, indulge in the luxury vibes at the Florida Keys Country Club, located 9 miles away. Enjoy a round of golf or relax at the club's amenities, creating unforgettable memories together in a picturesque setting.

Things to do recommended for families

Families vacationing in Grassy Key can explore the beautiful Dolphin Research Center, where kids can interact with dolphins and learn about marine life. They can also enjoy a day at the nearby Bahia Honda State Park, perfect for swimming, picnicking, and hiking along stunning beaches.

Things to do recommended for groups

Explore the stunning waters of the Florida Keys with a group snorkeling adventure at Sombrero Reef or enjoy a relaxing day at the beach with paddleboarding. Don't miss the chance to experience a sunset cruise for breathtaking views and unforgettable memories.

*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 you're planning a trip—whether it's with friends, family, pets, or for an extended stay—be sure to prioritize your preferences when filtering options. Here are some helpful Vrbo booking tips for you.

  • Traveling to Grassy Key with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and many more on Vrbo.
  • Traveling to Grassy Key with young kids: Traveling with young kids can be quite demanding. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, keeping in mind the distance to family-friendly attractions can enhance your experience.
  • Taking your pets with you to Grassy Key: For many families, a vacation wouldn't be the same without their furry companion. If that resonates with you, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and cozy beds, ensuring that everyone feels at home.
  • Planning for a long term stay visiting Grassy Key: If you're in search of vacation rentals that offer great deals for month-long stays, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rental options. Don't forget to include features 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 offers a delightful escape in the Florida Keys, boasting sandy beaches and tropical cottages perfect for family vacations. Explore the nearby reefs for incredible snorkeling adventures or relax in the charming atmosphere filled with friendly locals and outdoor recreation. With its idyllic setting and warm hospitality, Grassy Key is an ideal destination for travelers seeking relaxation and adventure in a beautiful island paradise.

  • Marathon: Marathon is a vibrant city located at the heart of the Florida Keys, with Grassy Key nestled within its boundaries. This destination is perfect for families, offering stunning beaches and outdoor activities. Enjoy a day at the beach or explore the local shopping mall and area. Notable attractions include family-friendly beaches and a bustling tourist precinct, making it an ideal spot for relaxation and fun. With its diverse range of resorts and recreational options, Marathon invites travelers to enjoy both adventure and leisure in a picturesque setting.
  • Key Colony Beach: Located 5 miles from Grassy Key, Key Colony Beach is a charming island city that offers a tranquil escape for families and beach lovers. Known for its beautiful shoreline and outdoor recreation, visitors can relish in the sun while enjoying various water sports or simply lounging on the beach. The area features delightful shopping options and recreational spaces, ensuring there’s something for everyone. With its serene ambiance and friendly community, Key Colony Beach is a perfect destination for those looking to unwind and enjoy family-friendly activities.
  • Duck Key: Just 3 miles from Grassy Key, Duck Key is a picturesque village renowned for its stunning island landscapes. This destination is ideal for outdoor enthusiasts and families seeking adventure and relaxation. Visitors can indulge in the local resorts and shopping areas or soak up the sun on the beautiful beaches. Duck Key's close proximity to family-friendly beaches makes it a great spot for making lasting memories. Whether you're swimming, dining, or exploring, Duck Key offers a delightful experience that captures the essence of the Florida Keys.

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 next adventure? Staying flexible with your travel dates can really pay off, as prices can vary quite a bit. Additionally, opting for an extended stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to narrow down options by price, location, and type of vacation rental. We're here to help you make the most of your travel experience.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board provides a convenient platform for you to plan new trips, manage your existing plans, and organize your bookings efficiently. The properties you’ve saved or reserved are neatly categorized into Potential, Upcoming, or Current Trips. To dive into your Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Delight in the beachside landscape of Grassy Key

The beaches and surrounding scenery provide a peaceful ambiance to your vacation 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 vacation rentals feature full kitchens and laundry facilities.

Exploring the beaches and other natural features in Grassy Key

Travelers enjoy Grassy Key for its seaside and sunsets. Whether you're looking for exciting outdoor activities or just want to take in the scenery, Grassy Key is a great spot to appreciate mother nature. These are a few of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city center:

  • 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

How much does it cost to rent a vacation rental in Grassy Key?
Length of stay, property type and season are some of the things that can influence the price of a vacation home. Simply enter your dates of travel to find your ideal match. From comfy cottages to expansive villas, all Vrbo vacation rentals provide unbeatable value.
How much does it cost to rent a beach house in Grassy Key?
The average price for a vacation rental close to the beach in Grassy Key will depend on when you're going and the style and size of property you're looking for. You can find prices easily and quickly on Vrbo by entering your travel dates. Then use our handy filter tool to select the number of bedrooms and amenities important to you, such as WiFi, air conditioning and a pool.
How old do you have to be to rent a vacation rental in Grassy Key?
The minimum age permitted can differ between properties on Vrbo, so be sure to look at the rules of the vacation rental in Grassy Key you want. But in general, it's 16, 18 or 21.
How long can I rent a vacation rental in Grassy Key for?
The amount of time you can stay in a Grassy Key vacation rental for is up to each property. Just enter your preferred travel dates to see options that offer extended stays. They have everything you need to make your extended vacation more convenient and enjoyable, such as laundries and air conditioning. Some vacation rentals may also offer weekly or monthly discounts, so you can stick around for longer for less.
Does Vrbo offer discounts for vacation homes in Grassy Key?
On Vrbo, we've got plenty of fantastic deals and discounts for Grassy Key. Check out our newly listed homes, as well as our weekly and monthly discounts on vacation rentals. Whether you're off on a mini getaway or a longer stay, Vrbo has a variety of options for all styles and budgets.

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