Grassy Key Holiday Rentals

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Holiday Rentals in Grassy Key

🌊 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

Sunsets in Paradise~ Gulf Front Pool Home, 22' Dock, Kayaks, Bikes & Paddleboards

9.0 out of 10, Wonderful, (24)
"Great property with great views."
Sunsets in Paradise~ Gulf Front Pool Home, 22' Dock, Kayaks, Bikes & Paddleboards

🌇 Ocean Sunset Views with Pool and Dock 🌇

9.0 out of 10, Wonderful, (37)
"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 🌇

Breeze On Inn: A Waterfront Retreat with 2 Bedrooms 2 bathrooms and Dockage

8.6 out of 10, Excellent, (9)
"Overall a great property but needs a few updates. Would still recommend and return."
Breeze On Inn: A Waterfront Retreat with 2 Bedrooms 2 bathrooms and Dockage

Morton Manor: Updated 9-Bed, 7.5-Bath Estate with Private Pool, Pickleball, Tiki

10.0 out of 10, Exceptional, (1)
"This house is spectacular! Not only did the size of the house (and it’s two separate guest houses on site) and amenities accommodate our group, but it was also outfitted in high end accessories that created an experience that was top notch. Even before we arrived, every question was answered quickly by the booking agent and the staff who help take care of the property were available at any time to address other questions we had while we were there (how to turn the heat on the hot tub). The house...
Morton Manor: Updated 9-Bed, 7.5-Bath Estate with Private Pool, Pickleball, Tiki

Casa De La Playa Oceanfront the Key to the Beach and 2 kayaks included

9.0 out of 10, Wonderful, (13)
"This is the first vacation for our three blended families. The house was just as the pictures indicated. We were able to kayak from the beach. The house was well stocked and cool when we arrived.we had a wonderful week. It is a great place to stay."
Casa De La Playa Oceanfront the Key to the Beach and 2 kayaks included

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

Skipjack Resort & Marina

3.0 star property
8.6 out of 10, Excellent, (1173)
"We really enjoyed pur stay at SkipJack. Rooms are super clean. Bar & grill onsite has excellent food. The extra amenities (courts, bikes, beach chairs) could use an update, but overall a veey nice stay."
The price is HK$1,931
HK$2,451 total
includes taxes & fees
27 Apr - 28 Apr
Skipjack Resort & Marina

Yacht Haven Marina

3.5 star property
9.8 out of 10, Exceptional, (136)
"The manatees came right to the patio. Was amazing. Didnt like the hidden cleaning fees tho, so gave 1 less star. Otherwise perfect experience"
The price is HK$1,388
HK$2,531 total
includes taxes & fees
27 Apr - 28 Apr
Yacht Haven Marina

Aqua Lodges at 47th Street Gulfside

3.0 star property
8.2 out of 10, Very good, (30)
"The view is incredible "
The price is HK$1,110
HK$2,218 total
includes taxes & fees
1 May - 2 May
Aqua Lodges at 47th Street Gulfside

Tropical Cottages

3.0 star property
8.4 out of 10, Very good, (799)
"Loved outdoor bath. Air worked great. Liked contactless checkin. "
The price is HK$1,047
HK$1,178 total
includes taxes & fees
11 May - 12 May
Tropical Cottages

Aqua Lodge Rentals At Coconut Cay

3.5 star property
9.6 out of 10, Exceptional, (157)
"Truly enjoyed our time in such a unique experience. "
The price is HK$1,466
HK$2,783 total
includes taxes & fees
27 Apr - 28 Apr
Aqua Lodge Rentals At Coconut Cay

Knight's Key Suites

3.0 star property
9.0 out of 10, Wonderful, (1104)
"Great Location"
The price is HK$1,000
HK$1,292 total
includes taxes & fees
8 May - 9 May
Knight's Key Suites

Cabins at Bonefish Bay

3.0 star property
10.0 out of 10, Exceptional, (39)
"We had a fantastic stay in the cabins. Very clean with everything you need. Quiet, cozy and the kayaks provided a unique way to see the island. We will definitely be back!"
Cabins at Bonefish Bay

Beach Residence / Private overwater dock / Heated Pool / Mahi Key

Beach Residence / Private overwater dock / Heated Pool / Mahi Key

The Reef at Marathon, Florida Keys

4.0 star property
8.8 out of 10, Excellent, (3)
"We really enjoyed staying at The Reef. I would say that it would have been a better experience if the washing machine worked properly- does not drain. Also we had to leave at 4 am to catch a flight- we should not be ask to take off the linens and put in the washing machine before leaving. It was not feasible. Thank you "
The Reef at Marathon, Florida Keys

Sunshine Key RV Resort & Marina

2.0 star property
8.8 out of 10, Excellent, (146)
"I enjoyed staying in a tiny house. The property was amazing!"
Sunshine Key RV Resort & Marina

PERFECT OCEAN FRONT/PRIVATE ELEVATOR/DOCK/HEAT POOL. MARATHON LIC PLR2017-00465

9.4 out of 10, Exceptional, (46)
"We stayed with Grandchildren and loved how the property was central to many attractions in the area. "
PERFECT OCEAN FRONT/PRIVATE ELEVATOR/DOCK/HEAT POOL. MARATHON LIC PLR2017-00465

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

9.6 out of 10, Exceptional, (119)
"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

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

10.0 out of 10, Exceptional, (253)
"Property was spacious and comfortable for our group of 6. Location was perfect/central within Marathon and the Keys. Best to drive to restaurants with kids to avoid busy road."
Coral Lagoon #13: Pool, Water Views, Both Gulf & Atlantic Access via Vaca Cut
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 types of properties in Grassy Key you may be interested in

Rainbow Bend Resort

2.5 star property
8.2 out of 10, Very good, (612)
"Great family vacation getaway. Super quiet and relaxing. Friendly staff and excellent food at the restaurant. If you’re looking to relax perfect destination. Sunrise views are spectacular. "
The price is HK$803
HK$1,252 total
includes taxes & fees
28 Apr - 29 Apr
Rainbow Bend Resort

Gulf View Waterfront Resort

2.5 star property
8.6 out of 10, Excellent, (447)
"Clean and curtious "
The price is HK$1,389
HK$1,562 total
includes taxes & fees
15 Apr - 16 Apr
Gulf View Waterfront Resort

Grassy Flats Resort & Beach Club

2.5 star property
9.4 out of 10, Exceptional, (265)
"beautiful rooms"
The price is HK$2,608
HK$2,934 total
includes taxes & fees
30 Apr - 1 May
Grassy Flats Resort & Beach Club
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.