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Grassy Key Rentals

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114 Houses

Relax Away- SOMBRERO BEACH- NEW 4BDRM W/ 40FT DOCK & POOL

Grassy Key house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$565

Unit 10, Furnished Studio located 50 yards from ocean

Grassy Key apartment

/ 1 bathroom / sleeps 2

Price per night from

$251

Sunset Catch- Gulf Front Home Incredible Views Pool Dock private and spacious

Grassy Key house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 7 minutes

Price per night from

$799

Unit 9, Furnished Studio located 50 yards from ocean

Grassy Key apartment

/ 1 bathroom / sleeps 2

Price per night from

$252

Efficiency 8a, located 50 yards from Ocean

Grassy Key studio

Studio / 1 bathroom / sleeps 2

Price per night from

$228

Glamping in the Florida Keys

Grassy Key caravan/mobile home

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$183

Great rentals within 20 miles that match your search

Amazing Ocean View Condo on the Beach!

Marathon apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Our Spirits were renewed!” Things don't happen by chance! Little did we know six months ago when we booked our vacation how much we would really, really NEED a quiet and peaceful week! This little corner of Marathon is exactly that: quiet and peaceful. The condo is very comfortably furnished, very clean, and the view is - well, I don't think there is a 'better' view anywhere! It's picture perfect - even to the gorgeous green iguana on the palm tree! (but you have to look quick - they move fast!). We had our son, daughter in law and two little grandkids with us...it was perfect! Sunrise with coffee by the pool, under the Chickee or on the patio...awesome! Lots to do for families or singles very close by...yup...you really can even have pizza delivered if you don't want delicious, fresh seafood!..and wow! are there some awesome spots for that!! Communication with the owners is impeccable...could NOT be better. These are the folks with whom you love to do business!! Thanks so much, Todd and Jamie!

Responds fast! avg. 2 hours 34 minutes

Price per night from

$341

Now booking Spring/Summer 2021! Dock, Bikes, Kayak, 2 beach clubs

Key Colony Beach house

2 bedrooms / 2 bathrooms / sleeps 5

“Wonderful Place to Stay” Place was exactly as described! Has all of the amenities needed for a relaxing, sun filled vacation! Pool, beach, location is perfect for any stay in the Florida Keys. Central to everything!

Responds fast! avg. 1 hour 34 minutes

Price per night from

$257

CHARMING KEY COLONY BEACH POOL COTTAGE, PVT POOL,46 FT DCK,WIFI

Key Colony Beach cottage

2 bedrooms / 2 bathrooms / sleeps 4

“Most wonderful vacation home ever.” The pool, the hammock, the dock, the decor....it was the best place i have ever stayed. I didnt want to leave. Laying in the hammock every night listening to the palm trees swaying in the breeze. Watching the snook hit the greenies over the underwater light at the dock. Taking a refreshing swim after a long day on the boat. An evening bike ride around key colony. It was everything we wanted on our vacation. And the house was decorated exactly as my own tropical retreat would be decorated, and it is such a comfortable home. I am hoping to come back for 2 weeks next summer.

Price per night from

$242

CARIBBEAN SOUL SAILING CHARTER Bayfront 2 BR cottage w/ 23 foot Sailboat or dock

Conch Key cottage

2 bedrooms / 1 bathroom / sleeps 6

“Perfect get-away cottage exceeded our expectations.” Just back from enjoying the cottage, Conched Out, at Caribbean Soul Charters on Conch Key. Awesome rustic cottage with tons of nautical character and a sailboat right out the back door. Great location near Marathon allowed us to easily day trip up to Key Largo and down to Key West. My family took the 23' Compact sailboat out 3 times during the week and the sailing was awesome. Our boat was in great shape and the motor operated flawlessly. One of the best family vacations we've ever enjoyed. We can't wait to come back. The owners, Barry and Tammy Jo, were very friendly and great sources of local information.

Price per night from

$325

Kokomo Cove Boat House

Marathon house

2 bedrooms / 2 bathrooms / sleeps 8

“Boat ramp and beautiful pool in the heart of the Keys” We wanted a house on a canal in the Marathon area, where we have been vacationing for years. This house had its own boat ramp, so we rented kayaks for a week and launched effortlessly right on site. The pool is lovely and relaxing. The house is well equipped and centrally located so trips up to Key Largo and down to Key West are quick.

Price per night from

$214

Royal Palm House

Marathon house

2 bedrooms / 2 bathrooms / sleeps 6

“Beautiful Home in Marathon” We truly loved this place, the home was clean, spacious and very comfortable! My husband still claims to this day that was the best sleep he has had in years and that's a big compliment coming from him! We loved having water access (although we didn't have a boat) it really made for some beautiful sunsets and sunrises! We found a couple of amazing restaurants that we visited on several occasions, the first and our favorite was Tarpon Creek following as a very close second was The Sunset Grill and Raw Bar, also our favorite breakfast spot became Juice Paradise Cuban Cafe (the best coffee). I'm only just now getting around to reviewing this place because we are planning another trip to the Keys in December and I was checking this place out and i didn't see our review and ask my husband about it (I thought he posted it and he thought I posted it), so finally 2 yrs later I'm giving our review!!! Unfortunately I see it's booked for our time frame and we are very disappointed about that but I know whoever booked it WILL NOT be disappointed! Thanks so much for an amazing experience, Gina & Scott PS we actually stayed Sept 2014 but it would only let me go back to Oct 2014! :-)

Price per night from

$214

OCEANFRONT LUXURY "Mar Azul"

Marathon house

3 bedrooms / 3 bathrooms / sleeps 7

Price per night from

$498

Florida Keys Beach Home Pool Fishing Diving

Marathon house

2 bedrooms / 2 bathrooms / sleeps 6

“Wonderful stay” Post hurricane and still a spectacular place to stay. Office staff was great. Free use of tennis court, rackets, and balls. Pool and jacuzzi were very excellent. TG

Price per night from

$285

OUTSTANDING Oceanfront House with Pool and Deep water dockage!!

Marathon house

4 bedrooms / 3 bathrooms / sleeps 10

“Marathon house” A great house with an awesome ocean view! The house was very clean and the kitchen was well stocked with all we needed. We especially looked the pool area and boat dock. It accommodated our 38 ft fishing boat we brought with no problems. I would highly recommend this rental

Responds fast! avg. 2 hours 34 minutes

Price per night from

$863

Island Time 1 (half of duplex)

Big Pine Key house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$125

Island Time 2 (half of duplex)

Big Pine Key house

3 bedrooms / 1 bathroom / sleeps 6

Price per night from

$128

Island Time (both halves of duplex)

Big Pine Key house

5 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$234

Our Island Thing

Big Pine Key house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$256

Villa Sombrero, Marathon

Marathon house

5 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$652

Reef Resort - Peaceful Getaway 204

Marathon condo

1 bedroom / 2 bathrooms / sleeps 4

“A lovely condo” The condo was nicely appointed and was a great mid location to explore the Florida Keys. The pool was large & refreshing. There were bikes, kayaks & paddle boats to use. We met a few residents who were very friendly. A very nice condo!

Price per night from

$301

Reef Resort Getaway 205

Marathon studio

Studio / 1 bathroom / sleeps 3

Price per night from

$236

500 Ocean - Tropical Florida Keys Vacation Home

Marathon house

2 bedrooms / 2 bathrooms / sleeps 6

“Zen Oasis with a Dock” Loved 500 Ocean. Quiet, Local, Relaxed. Great location, Good fishing and amenities for the boat ( tons of dock space, bait freezer, fish cleaning station) You have to watch that canal though it's super shallow (as in barely 2 feet most of the way). Everything is the house was nice and comfortable. Coconut Chuck was super helpful with our stay and provided a lot of information ahead of time!

Responds fast! avg. 1 hour 49 minutes

Price per night from

$113

Palm Cottage - Upscale, 2BR/2BA, Cabana Club Pool

Key Colony Beach house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$228

Florida Keys Fishing & Diving, waterfront Home heated pool, deep dock, parking

Marathon house

4 bedrooms / 5 bathrooms / sleeps 10

“PERFECT multi-family” House was great for us, our kids, and another family. It's a split-living type house, and was PERFECT!!! The pool was very nice, not too small. We spend most of the time on the boat, or in the pool. DEFINITELY recommend this house!!!!

Price per night from

$970

Best waterfront view in Marathon, pool, golf, dock

Marathon condo

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$152

Outstanding Oceanfront Condo on the Beach!!

Marathon condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 34 minutes

Price per night from

$341

Price per night from

$314

Ocean Side View on Canal, Great for Fishing, Near Sombrero Beach & Restaurants

Marathon Shores house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$685

Get out of the cold Feb.5-12, 2018 in Florida Keys at Marathon,The Hammocks

Marathon Shores villa

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$491

The Beach Hut

Marathon Shores condo

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$250

Waterfront fun and funky , Beautiful Duck Key

Duck Key condo

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$325

Paradise with or without a boat Clean Waterfront Beach Near Pet free

Marathon Shores house

2 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 17 minutes

Price per night from

$340

Key Colony Beach Home

Key Colony Beach house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 9 minutes

Price per night from

$263

Duck Key 50% off October

Duck Key house

3 bedrooms / 2 bathrooms / sleeps 9

Responds fast! avg. 4 minutes

Price per night from

$656

"Gulfside Grouper", Waterfront-Ground floor, 60' Dockage, Pool/Hot Tub, Pets OK

Marathon Shores house

4 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$978

PARADISE OCEAN FRONT HOME

Marathon house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 2 hours 56 minutes

Price per night from

$628

Harbour Dream~3/2..DKKB24~McGinnis

Duck Key house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 8 minutes

Price per night from

$671

Viewing 38 of 114
rentals in Grassy Key

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