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Compare 1040 Vacation Homes in Grassy Key with updated reviews, rates, and availability.

Aqua Lodge Rentals At Coconut Cay

3.5 star property
9.6 out of 10, Exceptional, (146)
"The property was easy to find and staying in a boathouse was a unique experience that we will certainly do again. The boathouse was spacious and comfortable and had everything we needed for our 2 night stay in Marathon."
The price is AED 757
AED 1,396 total
includes taxes & fees
12 Mar - 13 Mar
Aqua Lodge Rentals At Coconut Cay

Beautiful Coral Lagoon #12 - Waterfront - Boat Slips Available at the Marina

10.0 out of 10, Exceptional, (128)
"Coincidentally a couple of days before we went a friend who is familiar with Coral Lagoon told us about its sinkhole which will need extensive construction to fix. As a result we learned after we booked but before we arrived about the 5’high chain link fence which walls off the canal from the condos on the east side, including #12. The lack of direct access to the water and the impaired view were disappointing since we spent most of our time on the porch. There was no active construction...
Beautiful Coral Lagoon #12 - Waterfront - Boat Slips Available at the Marina

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

WOW! WATERFRONT CANAL HOME-RELAXING, FRESH & CLEAN-FISH, SWIM, SNORKEL CLOSE BY!

9.6 out of 10, Exceptional, (77)
"Great stay, lovely setting and location! Our second time here!"
WOW! WATERFRONT CANAL HOME-RELAXING, FRESH & CLEAN-FISH, SWIM, SNORKEL CLOSE BY!

Fishing and Family Fun paradise Oceanfront 60'ft dock 3 bed 2bath private pool

10.0 out of 10, Exceptional, (22)
"This property was in a great location. The neighborhood was quiet and convenient to everything. The view was fabulous and we spent many hours on the covered patio. The home & beds were very comfortable and the owner was quick to respond to questions. We'll be back next year."
Fishing and Family Fun paradise Oceanfront 60'ft dock 3 bed 2bath private pool

Large Full Duplex with Pool / Hot tub Pet Friendly 581- 591 10th Street

10.0 out of 10, Exceptional, (6)
"This place looks recently renovated. Very fresh and clean. It has a hot tub also that I don’t remember seeing in the description (bonus)!! Very short walk to a small beach. Located dead center of the keys which makes it an excellent place for divers. Short drive up or down the keys so all dive locations are easy to drive to in the morning. All in all a perfect location for someone that wants to visit all the keys during their trip. Pricing is very reasonable. Couldn’t be happier with our...
Large Full Duplex with Pool / Hot tub Pet Friendly 581- 591 10th Street

Oceanfront PARADISE w Heated pool, 55’ dock, ocean view & bathroom in every room

10.0 out of 10, Exceptional, (10)
"We came here for a week in February and totally enjoyed it. Loved having our own pool and plenty of space for everyone. "
Oceanfront PARADISE w Heated pool, 55’ dock, ocean view & bathroom in every room

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

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

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

Beautiful Waterfront Home Perfect for Fishing.

9.4 out of 10, Exceptional, (102)
"What a wonderful experience. Our family had such a great time!"
Beautiful Waterfront Home Perfect for Fishing.

★Newly remodeled tropical townhome★ Private plunge pool close to fun activities

10.0 out of 10, Exceptional, (37)
"Loved staying in the Keys. Townhome was clean and neat and had everything we needed for the stay. Extra special touches with snacks and toiletries provided when we got there. Communication with Miguel was wonderful and information for the area and recommendations for fishing guides provided were spot on. Plunge pool and outdoor areas were really nice additions. Would highly recommend this rental. "
★Newly remodeled tropical townhome★ Private plunge pool close to fun activities

NEW 4 Bedroom/3 Bath Home w/Private Pool,40 ft. Dock near Sombrero Beach!

10.0 out of 10, Exceptional, (54)
"My family and I had a great stay! The property was perfect for the 8 of us. "
NEW 4 Bedroom/3 Bath Home w/Private Pool,40 ft. Dock near Sombrero Beach!

Private Pool Oasis - Centrally Located in Florida Keys

10.0 out of 10, Exceptional, (26)
"Absolutely loved our time at this house. Cameron was a great host and the place is even better than the photos! 100% recommend for all ages"
Private Pool Oasis - Centrally Located in Florida Keys

Key Colony Beach Paradise

9.0 out of 10, Wonderful, (44)
"Overall we enjoyed our stay. We could tell the owner’s family has enjoyed the property, which provides a certain warmth. Owners must be short of stature. Low toilets and mirrors (at 5’9” I could not see my entire face w/o squatting a bit). No usable closet in MBR. Wild life in the canal-including a manatee! Plenty of towels for bath and beach. Everyone we met was friendly at Key Colony. Very quiet. Owner was quick to respond to inquiries. Hot tub was quite clean. We would return, except maybe...
Key Colony Beach Paradise

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

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

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

10.0 out of 10, Exceptional, (69)
"First time visiting the Keys and this property was one of the nicest we have stayed in. Very clean with lots of amenities ( kayaks, swim spa, gas grill, etc). Access to the canal and the use of kayaks was a huge plus! Manatees came right up to the dock several times while we were there!! Took the kayaks out to the mangroves and really enjoyed seeing the birds and sea life. The kayaks don't have seat bacs, but we used the lifejackets for that and that worked well.The only "negative" of the trip...
Don't Miss This! Deep Water Canal, Swimspa Pool, Kayaks, Walk to Tiki Bars!!

★Welcoming Family Vacation Gated home★with private heated pool and Patio

10.0 out of 10, Exceptional, (51)
"Very clean, well appointed, and comfortable beds and other furniture. VRBO home run!"
★Welcoming Family Vacation Gated home★with private heated pool and Patio

Waterfront home perfect for fishing, water sport, fam fun in Marathon FL keys

10.0 out of 10, Exceptional, (60)
"My husband and I and our pup had a great time at Fisherman’s paradise. The pool was very nice and clean and the house itself was spotless. Located in a quiet safe neighborhood but literally all that we needed was within 10 minutes of the house. Nancy was an awesome very responsive and friendly host. The only thing we missed was having our own boat there. Also highly recommend going to have a meal or get fresh fish from this place Brutus. Right around the corner and was the best meal we had! "
Waterfront home perfect for fishing, water sport, fam fun in Marathon FL keys

DUPLEX IN DUCK KEY Grand 3/2 W/90' Private Dock, Trailer Storage included

10.0 out of 10, Exceptional, (142)
"Gorgeous spot, pleasantly surprised1! The only tricky part was the house is a duplex, and it was unclear which half was ours, but my call to the owner was answered promptly and we were all set. Would definitely rent this place again!!"
DUPLEX IN DUCK KEY Grand 3/2 W/90' Private Dock, Trailer Storage included
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

Oceanfront Sandy Beach Vacation Rental Unit 2

9.6 out of 10, Exceptional, (130)
"Nice comfortable rental, as described not a swimming beach but great views over the Atlantic. Great mid Keys location. Owner responded to the few problems that we had. Nice birding right across the highway in some backwater ponds!"
Oceanfront Sandy Beach Vacation Rental Unit 2

🌇 Ocean Sunset Views with Pool and Dock 🌇

9.2 out of 10, Wonderful, (36)
"Great property, loved the pool,screened porch, pier for fishing and just great views, Host was great. We locked ourselves out once and he sent somebody to resolve the issue in less than 10 minutes.Place is kind of "Old School"but it was right for us. Gives of a good classic Keys Vibe,"
🌇 Ocean Sunset Views with Pool and Dock 🌇

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
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.