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Check prices for these dates

Next weekend
4 Rab. II - 6 Rab. II
In two weeks
11 Rab. II - 13 Rab. II
In one month
25 Rab. II - 27 Rab. II
In two months
23 Jum. I - 25 Jum. I

Compare 1303 Vacation Homes in Grassy Key with updated reviews, rates, and availability.

Aqua Lodge Rentals At Coconut Cay
Front of property

Aqua Lodge Rentals At Coconut Cay

3.5 star property
9.6 out of 10, Exceptional, (147)
"Loved, loved our stay, so peaceful out on the back porch having our morning coffee. So clean and stocked with all the things you need. Perfect for two people or a couple and two small kids. The free bikes were great. We will definely be back again. Thank you "
The price is SAR 773
SAR 1,426 total
includes taxes & fees
1 Apr - 2 Apr
Aqua Lodge Rentals At Coconut Cay
Dragonfly Lite – A tropical oasis with your own heated saltwater pool to enjoy!
Terrace/patio

Dragonfly Lite – A tropical oasis with your own heated saltwater pool to enjoy!

10.0 out of 10, Exceptional, (83)
"Beautiful outdoor patio, amazing pool, and a very well air conditioned house. We had a great week here, only thing we wished was different was the jacuzzi connected to the pool was the same temperature as the pool, other than that, fantastic host and property. "
Dragonfly Lite – A tropical oasis with your own heated saltwater pool to enjoy!
Coral Lagoon Single Family Home 3bed/2.5bath with 40' Boat Slip w/ Power + Water
Outdoor pool, a heated pool

Coral Lagoon Single Family Home 3bed/2.5bath with 40' Boat Slip w/ Power + Water

9.8 out of 10, Exceptional, (91)
"The host was extremely responsive to any requests that we had. We loved the stay, great location. The house met all of our needs. Walkable area to some things. The host was very helpful and accommodating, would definitely recommend. "
Coral Lagoon Single Family Home 3bed/2.5bath with 40' Boat Slip w/ Power + Water
Best Deals in Duck Key . 2 Bedroom /2 Bath w/40' 'Dock, Trailer Storage Incl,
Marina

Best Deals in Duck Key . 2 Bedroom /2 Bath w/40' 'Dock, Trailer Storage Incl,

10.0 out of 10, Exceptional, (166)
"We had the best week at this home. The house was extremely clean, decorated so cute, and was in a perfect location! The canal was amazing, we spent the days fishing and paddle boarding in it. The owner was so kind and helpful and was always available for questions! We will absolutely be back! "
Best Deals in Duck Key . 2 Bedroom /2 Bath w/40' 'Dock, Trailer Storage Incl,
COZY FAMILY HOME-POOL-HOTTUB -5 minute drive to sombrero beach-private property
Terrace/patio

COZY FAMILY HOME-POOL-HOTTUB -5 minute drive to sombrero beach-private property

10.0 out of 10, Exceptional, (34)
"Everything in the listing was completely accurate. Halfway point in the Keys. The home was very clean. Air Conditioning was spot on. We used the pool/hottub a lot. Surprised how much we used the hot tub as almost every day it was clear and hot. Although it didn’t bother us, the home is located in the direct path of a variety of planes jets and helicopters landing at Airport nearby. Noise was quite loud and may scare some dogs. Our Morkie had no issues. Definitely would rent property...
COZY FAMILY HOME-POOL-HOTTUB -5 minute drive to sombrero beach-private property
Oceanfront 165ft beach-Dock-Heated pool-4K sq.ft 4 bed/5 bath-Next avail 5.17.25
Terrace/patio

Oceanfront 165ft beach-Dock-Heated pool-4K sq.ft 4 bed/5 bath-Next avail 5.17.25

9.8 out of 10, Exceptional, (79)
"Three generations of our family enjoyed a wonderful vacation at The Last Resort. The house was beautifully appointed and well stocked as described in the listing. It had everything we needed for a memorable beach vacation. The owner was friendly, helpful, and easy to communicate with. We hope to return! back!ThownerfrieThowwith. "
Oceanfront 165ft beach-Dock-Heated pool-4K sq.ft 4 bed/5 bath-Next avail 5.17.25
2499 Rental Rate ANY WEEK March-Aug 2025 fees and taxes add, except holidays
Outdoor pool, a heated pool

2499 Rental Rate ANY WEEK March-Aug 2025 fees and taxes add, except holidays

9.6 out of 10, Exceptional, (118)
"My family (10 of us all together) stayed at this beautiful property and could not have been more pleased! It was spacious enough for all of us and close to all the things we wanted to do! Beth was super responsive anytime we reached out to her! The only thing I would note is that the house is in the DIRECT landing path for the airport down the road. It was a little startling when some of the jets were flying in. This is nothing against the house itself, just something to be aware of.We hope to...
2499 Rental Rate ANY WEEK March-Aug 2025 fees and taxes add, except holidays
VR65 Beach Nuts | 4 Bed, 2 Bath Next to Sombrero Beach
Beach

VR65 Beach Nuts | 4 Bed, 2 Bath Next to Sombrero Beach

9.6 out of 10, Exceptional, (46)
"Overall it was good. They could use more cooking bowls and sharper knives"
VR65 Beach Nuts | 4 Bed, 2 Bath Next to Sombrero Beach
Spacious Waterfront Home on a Direct Ocean Access Canal with a Chilled Pool
Outdoor pool, a heated pool

Spacious Waterfront Home on a Direct Ocean Access Canal with a Chilled Pool

9.6 out of 10, Exceptional, (65)
"Nice property with good amenities-especially for young children. Some things were not as advertised. "
Spacious Waterfront Home on a Direct Ocean Access Canal with a Chilled Pool
🌴Beach, Pool, Dock,Boating, and Golfing Paradise!!🌴Pets Welcomed!
Aerial view

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

10.0 out of 10, Exceptional, (45)
"Great week in the Keys! This property has amazing outdoor space! Great fishing off the dock, easy access to Sisters Creek and the Atlantic. The pool area is perfect and well kept. Very quiet and private neighborhood and close to everything, restaurants, grocery store, and beach. The house is well equipped and has COLD A/C, it is a bit dated but suited our family and friends just fine. We are outside people and just need a place to shower and recoup for the next day.. We would definitely stay...
🌴Beach, Pool, Dock,Boating, and Golfing Paradise!!🌴Pets Welcomed!
Coral Lagoon #13: Pool, Water Views, Both Gulf & Atlantic Access via Vaca Cut
Beach towels

Coral Lagoon #13: Pool, Water Views, Both Gulf & Atlantic Access via Vaca Cut

10.0 out of 10, Exceptional, (251)
"Highly recommend staying at this condo. "
Coral Lagoon #13: Pool, Water Views, Both Gulf & Atlantic Access via Vaca Cut
Bikini Bottom - 3 Bedroom Home Canal With Boat Lift - Rental Lic# VACA-23-244
Smart TV

Bikini Bottom - 3 Bedroom Home Canal With Boat Lift - Rental Lic# VACA-23-244

9.8 out of 10, Exceptional, (15)
"This place was nice and had some updates. The biggest thing for us is cleanliness. The housekeeper on the property needs to do a thorough job vacuuming and a least wash the floor every now and then. There were LONG dark hairs all over the place. That’s what prompted us to vacuum and the floor “looked” clean but was dirty. We washed the area we were using. We only used the main bedroom and the bed was very comfortable. The bathroom had been updated in recent years and was very roomy. The...
Bikini Bottom - 3 Bedroom Home Canal With Boat Lift - Rental Lic# VACA-23-244
Home in Marathon w/ boat lift
Fridge, microwave, oven, stovetop

Home in Marathon w/ boat lift

Home in Marathon w/ boat lift
Luxury Waterfront Oasis w Heated Pool and 50' Dock
On the beach, beach towels

Luxury Waterfront Oasis w Heated Pool and 50' Dock

10.0 out of 10, Exceptional, (26)
"Our family had an absolutely wonderful stay at this fantastic property! From the moment we arrived, we were impressed by how clean, spacious, and well-equipped the home was. It was the perfect size for our group, with plenty of room for the kids to play and the adults to relax. The kitchen had everything we needed to cook meals together, which was a huge plus for our family. The beds were super comfortable, and the living areas were cozy and inviting—perfect for our movie nights. The outdoor...
Luxury Waterfront Oasis w Heated Pool and 50' Dock
KCB-access Private Cabana Club, Dock on Canal, PET Friendly, Pickle ball courts
On the beach

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

9.4 out of 10, Exceptional, (78)
"The property was very nice and well maintained. The location was good. A couple lawn chairs for the patio/dock would be great."
KCB-access Private Cabana Club, Dock on Canal, PET Friendly, Pickle ball courts
Manatee Bay: Escape to this 2BR Duck Key Villa, Private Patio, Dip Pool & Easy Access to Marathon
Pool

Manatee Bay: Escape to this 2BR Duck Key Villa, Private Patio, Dip Pool & Easy Access to Marathon

9.8 out of 10, Exceptional, (27)
"Excellent location off the main drag with quiet stay and perfect place to have as a base of operation for sightseeing and fishing."
Manatee Bay: Escape to this 2BR Duck Key Villa, Private Patio, Dip Pool & Easy Access to Marathon
Open Water views, 100' dock Private Pool Ice machine DIRECT ACCESS open water
Outdoor pool, a heated pool

Open Water views, 100' dock Private Pool Ice machine DIRECT ACCESS open water

10.0 out of 10, Exceptional, (146)
"Pool and hot tube was great Househad everything you need for a long stay "
Open Water views, 100' dock Private Pool Ice machine DIRECT ACCESS open water
Don't Miss This! Deep Water Canal, Swimspa Pool, Kayaks, Walk to Tiki Bars!!
Terrace/patio

Don't Miss This! Deep Water Canal, Swimspa Pool, Kayaks, Walk to Tiki Bars!!

10.0 out of 10, Exceptional, (70)
"We had a wonderful time during our stay in the Florida Keys! The home and adjacent canal lot were spacious, comfortable, and very inviting. We completely recommend staying at Kathy's property!"
Don't Miss This! Deep Water Canal, Swimspa Pool, Kayaks, Walk to Tiki Bars!!
Beach House, Waterfront, Sombrero Beach, Florida Keys Rental, Private Pool, Dock
Outdoor pool, a heated pool

Beach House, Waterfront, Sombrero Beach, Florida Keys Rental, Private Pool, Dock

10.0 out of 10, Exceptional, (17)
"This property was amazing. The kids had plenty to do at the house and it was only a short walk to the beach. Perfect location. Can’t wait to come back again!"
Beach House, Waterfront, Sombrero Beach, Florida Keys Rental, Private Pool, Dock
Paradise Oceanside Estate- 6 Bedrooms & 9 BR + Office + Theater Room – SLEEPS 14
Aerial view

Paradise Oceanside Estate- 6 Bedrooms & 9 BR + Office + Theater Room – SLEEPS 14

Paradise Oceanside Estate- 6 Bedrooms & 9 BR + Office + Theater Room – SLEEPS 14
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Grassy Key

Waterfront Beauty 8-guests, Dock, Kayaks and more
Marina

Waterfront Beauty 8-guests, Dock, Kayaks and more

10.0 out of 10, Exceptional, (7)
"Wow! We enjoyed this beautiful home and had everything we could possibly need. The house has more than you need and it is clean and the beds are very comfortable. All the furniture was comfortable and the outdoors are amazing. I can’t describe just how special this home feels. I would highly recommend."
Waterfront Beauty 8-guests, Dock, Kayaks and more
Oceanfront Spanish Villa: 4 bed, loft, 8 guests
Outdoor dining

Oceanfront Spanish Villa: 4 bed, loft, 8 guests

2.0 star property
10.0 out of 10, Exceptional, (1)
"Best house ever. Very friendly host and ready to please with any requests. The beds were top quality. The house is perfect for families, the kitchen is great to cook, they have games, fishing poles and is very clean. We have never seen such beautiful sunsets. Easy to get to from anywhere in the country. Marathon is a unique destination, great food, quaint and you don’t get tired of coming back every year. WE RECOMMEND THIS HOUSE."
Oceanfront Spanish Villa: 4 bed, loft, 8 guests
🌊 Private Oasis With Pool Spa Dock and Ocean right in your backyard 🌊 allow pets
Outdoor pool, a heated pool

🌊 Private Oasis With Pool Spa Dock and Ocean right in your backyard 🌊 allow pets

9.2 out of 10, Wonderful, (40)
"Most an amazing place, with an amazing view. Frank was great to work with if had any questions or needs. We have been coming down to Marathon for 10 years and had one place we rented be sold, this was our first year at this location. So private, pool was amazing, kitchen had everything you need, all bedrooms had own bathroom, screen porch had unreal views. We will definitely be back next year and hopefully many years in the future. A little piece of heaven on earth."
🌊 Private Oasis With Pool Spa Dock and Ocean right in your backyard 🌊 allow pets
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.