Photo by Monica Ferro

Grassy Key holiday rentals

We found 1,983 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Grassy Key

Showing deals for:13 Nov - 20 Nov

Living area
Exterior
Pool
Private kitchen
Exceptional
(45 reviews)

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

Marathon

7% off
S$7,419
for 7 nights, 1 home
S$1,060 per night
includes taxes & fees
Fisherman Paradise, Dock, Pool , Ice Machine, Jacuzzi.
Second entrance to out large deep water dock
Pool and Spa and seating
Plenty of dock plus a floating kayak and jet ski dock
Living area
Exceptional
(53 reviews)

🌴Beach, Pool, Dock,Boating, and Golfing Paradise!!🌴Pets Welcomed!

Marathon

7% off
S$4,738
for 7 nights, 1 home
S$677 per night
includes taxes & fees
🌴Beach, Pool, Dock,Boating, and Golfing Paradise!!🌴Pets Welcomed!
Roomy kitchen
Exterior
View from the lanai. 🐠🌴☀️🎣
Pool
Exceptional
(111 reviews)

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

Marathon

8% off
S$6,016
for 7 nights, 1 home
S$859 per night
includes taxes & fees
Beautiful Canal front w/ dock - private pool -4/3~walk to beach~Outdoor smart tv
Family-style dining space with open concept for effortless entertaining.
Heated waterfront pool with loungers, tropical landscaping, and canal view.
Relaxing porch area with tropical breeze and waterfront backdrop.
Open, fully equipped kitchen perfect for preparing family meals together.
Exceptional
(133 reviews)

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

Marathon

9% off
S$4,552
for 7 nights, 1 home
S$650 per night
includes taxes & fees
Salty Anglers: Waterfront Heated Pool, Dock & Walk to Sombrero Beach in Marathon
View from the kitchen into the dining and living room
Property grounds
Exterior
View from the balcony
Exceptional
(33 reviews)

New Paradise On Sombrero Beach

Marathon

7% off
S$5,407
for 7 nights, 1 villa
S$772 per night
includes taxes & fees
New Paradise On Sombrero Beach
Relax poolside with a cold drink and a hot book
Pool
The spacious living and dining room makes it easy for everyone to be together
A little bamboo grove on the way to the canal out back
Exceptional
(78 reviews)

Sombrero Beach Home - Heated Pool, Kayaks, Private Road

Marathon

8% off
S$5,858
for 7 nights, 1 home
S$837 per night
includes taxes & fees
Sombrero Beach Home - Heated Pool, Kayaks, Private Road
Dining
Exterior detail
Interior
Pool
Very good
(6 reviews)

New Keys Cabins. Family sized cabins with full kitchens,

Marathon

8% off
S$3,176
for 7 nights, 1 cabin
S$454 per night
includes taxes & fees
New Keys Cabins. Family sized cabins with full kitchens,
Full Kitchen/Island/ living room and front entrance
Pool/Spa
Fire pit, boat lift, fishing table, cabana, outside chairs
Kitchen Cabinets
Exceptional
(5 reviews)

BEST House in Marathon With Ocean View!

Marathon

7% off
S$7,885
for 7 nights, 1 home
S$1,126 per night
includes taxes & fees
BEST House in Marathon With Ocean View!
A great way to start the day before jumping on the boat
Paradise found!
A complete kitchen with everything you will need to cook family meals at home!
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
S$4,589
for 7 nights, 1 home
S$656 per night
includes taxes & fees
Welcome to Paradise! Private Pool, 40' Dock, Great Location
Pool
Dining
Private kitchen
Room
Exceptional
(36 reviews)

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

Marathon

8% off
S$6,016
for 7 nights, 1 home
S$859 per night
includes taxes & fees
Harbor Hideaway - 3bed,2bath,50' dock, heated pool, tiki with all the amenities.
Interior
Property grounds
Room
Dining
Exceptional
(54 reviews)

Convenient central Marathon location, canal view.

Marathon

7% off
S$1,886
for 7 nights, 1 home
S$269 per night
includes taxes & fees
Convenient central Marathon location, canal view.
Fully equipped Kitchen including children dishware
Situated in a Gated Community
Walking distance to Duck Key Marina, water sports and a small beach.
Private heated pool with plenty of seating and outdoor games
Exceptional
(42 reviews)

Private Pool Oasis - Centrally Located in Florida Keys

Marathon

7% off
S$4,851
for 7 nights, 1 home
S$693 per night
includes taxes & fees
Private Pool Oasis - Centrally Located in Florida Keys
Canal-side living! Say hello to passing boaters, paddlers & kayakers.
A common walkway leads to Conch Cottage: Vacation vibes on Harbor Village Drive!
Enjoy a morning coffee out on your private balcony.
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
S$4,400
for 7 nights, 1 villa
S$629 per night
includes taxes & fees
Hawks Cay Island Retreat - Duck Key - Pool & Patio
Property grounds
Pool
Interior
Marina
Exceptional
(15 reviews)

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

Marathon

7% off
S$4,429
for 7 nights, 1 villa
S$633 per night
includes taxes & fees
Isla Marlin 28: Palm lined luxury villa w/dockage and sunset views
Private kitchen
Room
Second bedroom
Dining
Wonderful
(21 reviews)

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

Marathon

7% off
S$2,400
for 7 nights, 1 home
S$343 per night
includes taxes & fees
Charming 2beds 2 baths w/pool 10 mins from the beach!
Cabana Club Pool
Terrace/patio
Interior
Private kitchen
Exceptional
(16 reviews)

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

Key Colony Beach

11% off
S$4,140
for 7 nights, 1 home
S$591 per night
includes taxes & fees
Updated 3/3, Cabana Club Pool Membership, Dock, Tiki Hut 15% off promo to 12/23
Pool
Ocean Views from Balcony
Private kitchen
Living area
Exceptional
(26 reviews)

Dock, Pool, FREE RAMP, Kayaks, Jacuzzi, Amazing Ocean Views Pets are Welcomed!

Marathon

7% off
S$3,886
for 7 nights, 1 home
S$555 per night
includes taxes & fees
Dock, Pool, FREE RAMP, Kayaks, Jacuzzi, Amazing Ocean Views Pets are Welcomed!
Exterior
Pool
Private kitchen
Property grounds
Exceptional
(11 reviews)

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

Key Colony Beach

7% off
S$3,216
for 7 nights, 1 home
S$459 per night
includes taxes & fees
Key Colony Beach Home Casa Sunny Sea Key Colony Beach, Fl Keys
Private kitchen
Interior
Living area
Living area
Exceptional
(21 reviews)

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

Marathon

7% off
S$3,697
for 7 nights, 1 home
S$528 per night
includes taxes & fees
Salty Air Retreat. 2 Bedroom 1 Bathroom Half Duplex. Dockside.
Over the rainbow
Pool
Dock you boat here. Underwater lighting for night fishing off of the dock. Fun!
Pull out sofa bed w/ comfortable mattress. Property #2178313 for more reviews
Exceptional
(39 reviews)

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

Key Colony Beach

7% off
S$3,117
for 7 nights, 1 home
S$445 per night
includes taxes & fees
Tropical Paradise 🏝! POOL, Hot Tub, Dock, FREE Ice, Kayaks, Paddles, Bikes!
Private kitchen
Fully redone villa
Exterior
Marina
Exceptional
(29 reviews)

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

Marathon

7% off
S$3,451
for 7 nights, 1 home
S$493 per night
includes taxes & fees
Majestic Marina View- 2/2.5 townhome looking over Hawks Cay Marina.
Cozy & comfy, perfect for family & friends time🌴
Bay views from the bar 🌘, Book your Holiday & 2024 dates now!
Privacy bamboo fence
Enjoy 100 plus channels and YouTube on 55-inch Samsung smart TV, watch Netflix
Exceptional
(135 reviews)

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

Key Colony Beach

8% off
S$3,565
for 7 nights, 1 home
S$509 per night
includes taxes & fees
CLEAR water views @Tiki haven! Quick ocean access, Pool, HotTub, FUN! FREE ICE!
Property grounds
Interior
Pool
Exterior
Exceptional
(9 reviews)

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

Marathon

8% off
S$5,948
for 7 nights, 1 home
S$850 per night
includes taxes & fees
Gated Villa w/ Private Pool, 70" TV, Patio, Carport & Fast Wifi
Property grounds
Living area
Room
Private kitchen
Exceptional
(25 reviews)

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

Key Colony Beach

6% off
S$2,066
for 7 nights, 1 home
S$295 per night
includes taxes & fees
Key Colony Home with Dock and Cabana Club Access- Pets Welcomed

  • 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

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 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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