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Grassy Key Rentals with Pools

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193 Houses in Grassy Key with pools

Efficiency 8a, located 50 yards from Ocean

Grassy Key studio

Studio / 1 bathroom / sleeps 2

Responds fast! avg. 3 hours 54 minutes

Match: Swimming pool

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Price per night from

$229

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

Grassy Key house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 1 hour 29 minutes

Match: Swimming pool

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Price per night from

$567

Unit 10, Furnished Studio located 50 yards from ocean

Grassy Key apartment

/ 1 bathroom / sleeps 2

Responds fast! avg. 3 hours 54 minutes

Match: Swimming pool

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Price per night from

$252

Unit 9, Furnished Studio located 50 yards from ocean

Grassy Key apartment

/ 1 bathroom / sleeps 2

Responds fast! avg. 3 hours 54 minutes

Match: Swimming pool

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Price per night from

$252

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

Grassy Key house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 44 minutes

Match: Swimming pool

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Price per night from

$687

Great rentals within 20 miles that match your search

Escape to Paradise --2 bedroom oceanfront condo on Coco Plum

Marathon apartment

2 bedrooms / 2 bathrooms / sleeps 5

“Beautiful location with lots to enjoy!!” This property is exactly as pictured! It was a wonderful vacation with an ideal location.It was right on the ocean so you could watch the sun rise through the screened lanai, along with other various ocean activities.The owners were wonderful to work with and even apologized about parking lot maintenance being completed during our visit, which was no big deal. Please be aware that the property has one of the rare sand beaches in the Keys but seaweed washes up also. Although it can be unsightly, it didn't bother me. The beachcomber does come every few days to clean it up. There was still plenty of sand to the left (North) for me to walk on the beach and search for baby shells. There are so many places to choose for dinners. I recommend Havanna Jack's for oceanfront dining, Florida Keys Steak and Lobster House for lobster, Burdine's for fries and sunset, and Key Colony Inn for early bird special.I truly enjoyed the Dolphin Research Center and also seeing a turtle release from the Turtle Hospital at Sombrero Beach. I enjoyed the heated pool every day because the weather was perfect! If you aren't familiar with the Keys, Marathon is the middle Key. We went to Key West for the day (1 1/2 hr drive) because my friend had never experienced it. The ladies at the Marathon Visitor Center were the best! Great souvenir shop was Marooned in Marathon. You will not believe how many unique gifts they have. I plan to return to this Coco Plum property if/when I am lucky enough to go back to the Keys! I feel we saw alot but there is still so much more to enjoy!

Match: Swimming pool

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Price per night from

$287

Spacious Top Floor Condo w/ Water View!!

Marathon apartment

3 bedrooms / 2 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$373

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. 3 hours 11 minutes

Match: Swimming pool

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Price per night from

$343

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

Key Colony Beach house

2 bedrooms / 2 bathrooms / sleeps 6

“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. 43 minutes

Match: Swimming pool

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Price per night from

$247

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.

Match: Swimming pool

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Price per night from

$235

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.

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Price per night from

$186

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

Match: Swimming pool

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Price per night from

$275

East Sister Rock Island

Marathon Shores house

3 bedrooms / 2 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$1,718

Villa Sombrero, Marathon

Marathon house

5 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 1 hour 14 minutes

Match: Swimming pool

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Price per night from

$654

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!

Match: Swimming pool

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Price per night from

$271

Reef Resort Getaway 205

Marathon studio

Studio / 1 bathroom / sleeps 3

Match: Swimming pool

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Price per night from

$196

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

Key Colony Beach house

2 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$229

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!!!!

Match: Swimming pool

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Price per night from

$974

Waterfront Get Hooked

Marathon house

4 bedrooms / 3 bathrooms / sleeps 10

“AMAZING” Beyond perfect. Beautiful home, has everything you need. Spotlessly clean. I will be renting again. I would recommend to families and friends to stay.

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Price per night from

$350

Match: Swimming pool

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Price per night from

$258

Private Heated Pool, New Boat Dock and Ready Enjoyment!

Key Colony Beach house

2 bedrooms / 1 bathroom / sleeps 4

“Keys” This house was awesome!! My family really enjoyed staying here! We plan on booking this house for next year already. It has everything you need! And it is fully renovated all throughout! We are happy we were able to find this!!

Match: Swimming pool

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Price per night from

$263

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

Match: Swimming pool

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Price per night from

$493

MARATHON MAJIC

Marathon house

3 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$287

Paradise Retreat with Special Rates!! Book Now and Save!!

Key Colony Beach condo

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 1 hour 26 minutes

Match: Swimming pool

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Price per night from

$188

The Beach Hut

Marathon Shores condo

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 15 minutes

Match: Swimming pool

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Price per night from

$251

House on 7th ST in KEY Colony Beach W/CABANA CLUB

Key Colony Beach house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 33 minutes

Match: Swimming pool

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Price per night from

$213

RENOVATED 2 BED MARATHON TOWNHOME w/ DOCK SPACE - WALK TO BEACH!

Marathon Shores townhouse

2 bedrooms / 3 bathrooms / sleeps 4

Match: Swimming pool

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Price per night from

$331

Family Friendly Boutique Resort with Heated Pool - Marlin Bay Resort & Marina

Marathon house

3 bedrooms / 3 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$499

Gated Luxury Resort with Private Bayside Marina - Marlin Bay Resort & Marina

Marathon house

3 bedrooms / 3 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$579

Spacious Home w/ Roof Top Deck & Gourmet Kitchen - Marlin Bay Resort & Marina

Marathon house

3 bedrooms / 3 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$579

Professionally Decorated Standalone 3 Story Home - Marlin Bay Resort & Marina

Marathon house

3 bedrooms / 3 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$499

Boutique Resort with Luxury Homes & Large Pool - Marlin Bay Resort & Marina

Marathon house

3 bedrooms / 3 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$579

Luxurious Hidden Gem with Gorgeous Sunset Views - Marlin Bay Resort & Marina

Marathon house

3 bedrooms / 3 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$699

Clean & Pristine w/ Roof Top Deck & Water Views - Marina Bay Resort & Marina

Marathon house

3 bedrooms / 3 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$579

The Ocean Never Felt So Close!

Key Colony Beach house

2 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$221

Key Colony Beach Home

Key Colony Beach house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 46 minutes

Match: Swimming pool

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Price per night from

$264

Duck Key 50% off October

Duck Key house

3 bedrooms / 2 bathrooms / sleeps 9

Responds fast! avg. 2 hours 11 minutes

Match: Swimming pool

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Price per night from

$567

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

Marathon Shores house

4 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 2 hours 28 minutes

Match: Swimming pool

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Price per night from

$430

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rentals in Grassy Key

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