Photo by Monica Ferro

Grassy Key holiday homes

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

Holiday rentals with weekly discounts – Grassy Key

Showing deals for:11 Dec - 18 Dec

Open, fully equipped kitchen perfect for preparing family meals together.
Heated waterfront pool with loungers, tropical landscaping, and canal view.
Relaxing porch area with tropical breeze and waterfront backdrop.
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

9% off
NZ$6,306
for 7 nights, 1 home
NZ$901 per night
includes taxes & fees
Salty Anglers: Waterfront Heated Pool, Dock & Walk to Sombrero Beach in Marathon
Exterior
Property grounds
Kitchen sitting area
View from the balcony
Exceptional
(34 reviews)

New Paradise On Sombrero Beach

Marathon

7% off
NZ$7,253
for 7 nights, 1 villa
NZ$1,036 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
NZ$10,032
for 7 nights, 1 home
NZ$1,433 per night
includes taxes & fees
Fisherman Paradise, Dock, Pool , Ice Machine, Jacuzzi.
Upstairs Lanai
Exterior
Roomy kitchen
View from the lanai. 🐠🌴☀️🎣
Exceptional
(112 reviews)

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

Marathon

8% off
NZ$8,088
for 7 nights, 1 home
NZ$1,155 per night
includes taxes & fees
Beautiful Canal front w/ dock - private pool -4/3~walk to beach~Outdoor smart tv
Room
Property grounds
Interior
Dining
Exceptional
(54 reviews)

Convenient central Marathon location, canal view.

Marathon

7% off
NZ$2,266
for 7 nights, 1 home
NZ$324 per night
includes taxes & fees
Convenient central Marathon location, canal view.
Pool
Exterior detail
Interior
Dining
Very good
(6 reviews)

New Keys Cabins. Family sized cabins with full kitchens,

Marathon

8% off
NZ$4,240
for 7 nights, 1 cabin
NZ$606 per night
includes taxes & fees
New Keys Cabins. Family sized cabins with full kitchens,
Marina
Exterior
Exterior
Dining
Exceptional
(12 reviews)

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

Marathon

9% off
NZ$32,294
for 7 nights, 1 home
NZ$4,613 per night
includes taxes & fees
Sleeps 10 - Private house with 110’ of Deep Water Dockage, Pool, Hot Tub & more!
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
NZ$8,242
for 7 nights, 1 home
NZ$1,177 per night
includes taxes & fees
Sombrero Beach Home - Heated Pool, Kayaks, Private Road
Fire pit, boat lift, fishing table, cabana, outside chairs
Pool/Spa
Kitchen Cabinets
Kitchen Island
Exceptional
(5 reviews)

BEST House in Marathon With Ocean View!

Marathon

7% off
NZ$10,662
for 7 nights, 1 home
NZ$1,523 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!
Conch Cottage from above, with so much more outdoor space than our neighbors.
Kick back, read, play board games & watch TV in the well-appointed living area.
Wonderful
(9 reviews)

Hawks Cay Island Retreat - Duck Key - Pool & Patio

Marathon

8% off
NZ$7,058
for 7 nights, 1 villa
NZ$1,008 per night
includes taxes & fees
Hawks Cay Island Retreat - Duck Key - Pool & Patio
Private kitchen
Outdoor dining
Living area
Dining
Exceptional
(32 reviews)

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

Marathon

7% off
NZ$6,441
for 7 nights, 1 home
NZ$920 per night
includes taxes & fees
Open Ocean View, Private Hot Tub, Ice Machine, Moor 26' Boat!
If Bananas are ripe then eat em
Pool
Huge Porch View 2
Its not a Mirage...its Mirage Manor
Exceptional
(38 reviews)

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

Marathon

8% off
NZ$7,917
for 7 nights, 1 home
NZ$1,131 per night
includes taxes & fees
Marathon 3BR on 55' Canal Boat Dock w Pool Spa Hot Tub Free pool heat bay side
Exterior
Marina
Sectional couch in living room
Pool
Exceptional
(60 reviews)

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

Marathon

7% off
NZ$5,880
for 7 nights, 1 villa
NZ$840 per night
includes taxes & fees
Marlin House 52: Gated Luxury Villa w/ Dockage, Sunset Views and Pool
Marina
Pool
Interior
Property grounds
Exceptional
(16 reviews)

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

Marathon

7% off
NZ$5,991
for 7 nights, 1 villa
NZ$856 per night
includes taxes & fees
Isla Marlin 28: Palm lined luxury villa w/dockage and sunset views
Interior
Room
Private kitchen
Second bedroom
Wonderful
(21 reviews)

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

Marathon

7% off
NZ$3,121
for 7 nights, 1 home
NZ$446 per night
includes taxes & fees
Charming 2beds 2 baths w/pool 10 mins from the beach!
Your arrival
Paradise found!
Relax and watch the kiddos in the pool
A complete kitchen with everything you will need to cook family meals at home!
Exceptional
(44 reviews)

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

Key Colony Beach

8% off
NZ$7,449
for 7 nights, 1 home
NZ$1,064 per night
includes taxes & fees
Welcome to Paradise! Private Pool, 40' Dock, Great Location
Property grounds
Pool
Exterior
Property grounds
Exceptional
(11 reviews)

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

Key Colony Beach

7% off
NZ$6,690
for 7 nights, 1 home
NZ$956 per night
includes taxes & fees
Key Colony Beach Home Casa Sunny Sea Key Colony Beach, Fl Keys
Private kitchen
Terrace/patio
Dining
Cabana Club Pool
Exceptional
(16 reviews)

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

Key Colony Beach

11% off
NZ$5,600
for 7 nights, 1 home
NZ$800 per night
includes taxes & fees
15% off promo to 12/23-Updated 3/3, Cabana Club Pool Membership, Dock, Tiki Hut
Pull out sofa bed w/ comfortable  mattress. Property #2178313 for more reviews
Pool
Over the rainbow
Dock you boat here. Underwater lighting for night fishing off of the dock. Fun!
Exceptional
(41 reviews)

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

Key Colony Beach

8% off
NZ$5,081
for 7 nights, 1 home
NZ$726 per night
includes taxes & fees
Tropical Paradise 🏝! POOL, Hot Tub, Dock, FREE Ice, Kayaks, Paddles, Bikes!
Our dock is a perfect place to enjoy your favorite evening beverage on
Grab a chair... We have a perfect place to enjoy your morning coffee
Take a walk to Sunset Park
Relax on a bench or at a table
Facilities on site
Hot tub next to the pool at the Private Cabana Club
Exceptional
(94 reviews)

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

Key Colony Beach

9% off
NZ$2,688
for 7 nights, 1 home
NZ$384 per night
includes taxes & fees
KCB-access Private Cabana Club, Dock on Canal, PET Friendly, Pickle ball courts
Property grounds
Pool
Exterior
Property grounds
Exceptional
(15 reviews)

Charming 3-Bedroom Villa Centrally Located in the Florida Keys

Marathon

7% off
NZ$6,320
for 7 nights, 1 villa
NZ$903 per night
includes taxes & fees
Charming 3-Bedroom Villa Centrally Located in the Florida Keys
Enjoy 100 plus channels and YouTube on 55-inch Samsung smart TV, watch Netflix
Bay views from the bar 🌘, Book your Holiday & 2024 dates now!
Privacy bamboo fence
Bright and blue, pool is heated December to March! Private pool and tiki bar..
Exceptional
(136 reviews)

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

Key Colony Beach

8% off
NZ$5,741
for 7 nights, 1 home
NZ$820 per night
includes taxes & fees
CLEAR water views @Tiki haven! Quick ocean access, Pool, HotTub, FUN! FREE ICE!
Marina
Property grounds
Private kitchen
Exterior
Exceptional
(203 reviews)

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

Marathon

8% off
NZ$8,473
for 7 nights, 1 home
NZ$1,210 per night
includes taxes & fees
Finest location in Coral Lagoon. End unit with bay views and boat slip!
Marina
Terrace/patio
Marina
Pool
Exceptional
(68 reviews)

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

Key Colony Beach

7% off
NZ$2,741
for 7 nights, 1 apartment
NZ$392 per night
includes taxes & fees
KCB-access Private Cabana Club,Dock on Canal,PET Friendly, Pickle ball courts
  • 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

  • Sandy Beaches: Enjoy Grassy Key’s pristine shores perfect for family picnics or a romantic stroll.
  • National State Parks: Explore lush parks offering outdoor adventures and local wildlife encounters.
  • Island Vibes: Experience the laid-back, welcoming community and scenic coastal charm.
  • Family-friendly Activities: Engage in a variety of outdoor pursuits suitable for all ages.
  • Picturesque Getaway: Unwind with the natural beauty and relaxed atmosphere unique to Grassy Key.

Top attractions near Grassy Key

Grassy Key, Florida, offers a blend of beautiful beaches, inviting national state parks, and a charming island vibe. Perfect for an outdoor or family holiday, visitors can enjoy a range of local attractions that celebrate both the natural culture and scenic beauty of the area. Whether you’re exploring the coastline or venturing into nature, Grassy Key is a delightful destination for a memorable escape.

  • Coco Plum Beach: A sandy haven with beach vibes, located 6km away, perfect for a relaxed day under the sun.
  • Little Conch Key: An island offering a blend of beach and outdoor experiences, 6km away, ideal for a leisurely exploration.
  • Curry Hammock State Park: A national state park 3km away, providing scenic outdoor adventures and a taste of local nature.

Things to do recommended for couples

Grassy Key offers a tranquil escape for couples. Enjoy a sunset kayak tour through the mangroves, or unwind with a beach picnic at Sombrero Beach. Don’t miss a romantic dinner at a waterfront restaurant, where you can savour fresh seafood while watching the sun dip below the horizon.

Things to do recommended for families

Families visiting Grassy Key can explore the fascinating marine life at the Dolphin Research Center, enjoy a day of fun at the nearby Sombrero Beach, and embark on an exciting kayak adventure in the beautiful waters of the Florida Keys, creating unforgettable memories together.

Things to do recommended for groups

Groups visiting Grassy Key can enjoy kayaking through mangroves, birdwatching, and local seafood feasts, immersing in the relaxing island vibe while reveling in the authentic Floridian coastal culture.

*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

If you're travelling with a group, family, or pets, or if you're considering longer stays, it's important to filter your options according to your priorities. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Grassy Key with a group: Think about how many bedrooms you’ll require, as well as features like a fully equipped kitchen or outdoor areas for socialising. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Grassy Key with young kids: Travelling with young kids can be quite demanding. It's important to prioritise their comfort and safety, as well as access to suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to attractions that are enjoyable for the whole family.
  • Taking your pets with you to Grassy Key: For many, a family holiday isn't truly complete without their furry companion. If that resonates with you, take a look at Vrbo listings that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring everyone feels comfortable and at home.
  • Planning for a long term stay visiting Grassy Key: If you're searching for holiday rentals with special offers for stays of a month or more, you've come to the right spot. By using the appropriate filters, 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 as well.

Where to stay near Grassy Key

Grassy Key offers a charming island getaway perfect for a family holiday or a romantic escape, complete with sandy beaches and outdoor adventures. Visitors can enjoy the relaxed atmosphere, explore the natural beauty and recreational activities, and experience the welcoming community spirit unique to the Florida Keys. Ideal for those seeking a laid-back retreat, Grassy Key invites travellers to unwind and create lasting memories on its picturesque island shores.

  • Marathon: Situated in the heart of the Florida Keys, Marathon is a vibrant city renowned for its stunning beaches and outdoor activities. With Grassy Key as part of Marathon, visitors can easily access family-friendly beaches and enjoy a range of water sports. The area boasts excellent shopping venues and recreational facilities that cater to all ages. Don't miss the chance to explore local landmarks, including the famous Seven Mile Bridge, which connects you to breathtaking views and delightful experiences.
  • Key Colony Beach: Just a short drive of 8km from Grassy Key, Key Colony Beach is a picturesque island city that invites visitors to unwind and explore. Known for its charming beach atmosphere, this destination is perfect for families looking to enjoy outdoor activities and soak up the sun. Key Colony Beach features well-maintained recreational areas and delightful shopping options, making it an ideal spot for a leisurely day. The pristine beaches here are perfect for swimming, sunbathing, or simply enjoying the serene surroundings.
  • Duck Key: Located merely 5km from Grassy Key, Duck Key is a quaint village that epitomises the laid-back island lifestyle. Surrounded by beautiful waters and lush landscapes, it’s a favourite for families and outdoor enthusiasts alike. Visitors can indulge in various activities, from water sports to shopping at local centres. The village's stunning beaches provide ample opportunities for relaxation and recreation, making it a perfect stop for those seeking a tranquil escape in 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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January70.9°F (21.6°C)No Rain (Dry)Mostly Sunny
February72.1°F (22.3°C)No Rain (Dry)Mostly Sunny
March73.2°F (22.9°C)No Rain (Dry)Mostly Sunny
April76.8°F (24.9°C)No Rain (Dry)Mostly Sunny
May79.3°F (26.3°C)Light RainMostly Sunny
June82.6°F (28.1°C)Light RainMostly Sunny
July84.0°F (28.9°C)Light RainMostly Sunny
August84.4°F (29.1°C)Light RainMostly Sunny
September83.5°F (28.6°C)Light RainMostly Sunny
October80.6°F (27.0°C)Light RainMostly Sunny
November76.5°F (24.7°C)Light RainMostly Sunny
December73.6°F (23.1°C)No Rain (Dry)Mostly Sunny

Booking with Vrbo is a breeze

Looking to cut costs on your next adventure? Try keeping your travel dates flexible – prices tend to vary, and you might snag a better deal. A longer stay could also save you a pretty penny. To discover the perfect Vrbo property that suits your budget, simply use our filters to sort by price, location, and rental type.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board provides a convenient platform for you to plan new adventures, refine your travel arrangements, or manage your bookings with ease. Your saved or booked properties are conveniently categorised into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.bookabach.co.nz/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)
  • Sunset Park Beach (5.5 mi / 8.9 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, Bookabach 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 Bookabach 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 Bookabach. 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 Bookabach, 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, Bookabach 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 Bookabach 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 Bookabach, 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 Bookabach'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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