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Grassy Key Rentals

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Price range

Per night

$10 - $500

Grassy Key Rentals

331 Houses

JINGLE ALL THE WAY to Relax Away - SOMBRERO- NEW 4BDRM W/ DOCK & PRIVATE POOL

Grassy Key house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 3 hours 14 minutes

Price per night from

$295

1 / 24

Unit 10, Furnished Studio located 50 yards from ocean

Grassy Key apartment

/ 1 bathroom / sleeps 2

Responds fast! avg. 1 hour 38 minutes

Price per night from

$150

1 / 37

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 21 minutes

Price per night from

$401

1 / 33

Paraidise with or witout boat

Grassy Key house

2 bedrooms / 2 bathrooms / sleeps 9

Price per night from

$250

1 / 22

Gulf Front Pool Home w/Privacy, Charm & Swat Mosquito System

Grassy Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$421

1 / 14

Beachfront Condo with Panoramic Ocean View! Paradise in the Florida Keys!

Grassy Key condo

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 1 hour 51 minutes

Price per night from

$225

1 / 27

Unit 9, Furnished Studio located 50 yards from ocean

Grassy Key apartment

/ 1 bathroom / sleeps 2

Responds fast! avg. 1 hour 38 minutes

Price per night from

$150

1 / 38

Efficiency 8a, located 50 yards from Ocean

Grassy Key studio

Studio / 1 bathroom / sleeps 2

Responds fast! avg. 1 hour 38 minutes

Price per night from

$140

1 / 36

P58 Grassy Key Delight--- 4 Bedroom With Pool

Grassy Key house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$429

1 / 17

Great rentals within 20 miles that match your search

Villa Sombrero, Marathon

Marathon house

5 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 2 hours 55 minutes

Price per night from

$394

1 / 31

FL Keys Waterfront Pool Home 2 Bedrooms Sleeps 8 w/ 60 Feet of Dockage

Marathon Shores house

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 hours 3 minutes

Price per night from

$201

1 / 26

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

Marathon apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Great condo with beautiful ocean views!!!!” We couldn't have picked a better condo and location!! Many great restaurants and bars only a few miles away. The pool was really nice overlooking the beach. The condo was nicely decorated and plenty of room

Responds fast! avg. 3 hours 39 minutes

Price per night from

$187

1 / 24

Keys Cove House 3

Marathon Shores house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 1 hour 13 minutes

Price per night from

$429

1 / 32

Waterfront Paradise with a heated pool and full dock in Marathon key, Florida

Marathon house

3 bedrooms / 3 bathrooms / sleeps 8

“Fabulous and Fun Getaway” This beautifully appointed three bedroom home has everything you need to have a fun vacation in the Keys. We really enjoyed the pool and the kayaks and the kids loved fishing from the dock. The sunsets were beautiful and

Responds fast! avg. 3 hours 52 minutes

Price per night from

$344

1 / 18

Vacation in the beautiful florida keys

Marathon Shores villa

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$201

1 / 8

P00 - 4 bdrm Pool home overlooking Sombrero Beach!

Marathon house

4 bedrooms / 4 bathrooms / sleeps 10

“Beach access great !” We had 10 in our party and had plenty of room. Three outside porches and one was screened in. All had fun in pool! Only thing I was disappointed with was the beach in front was not cleaned yet from Hurricane and was roped off,

Price per night from

$308

1 / 23

Manatee Haven

Marathon house

3 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 2 hours 37 minutes

Price per night from

$251

1 / 8

Dragonfly Lite a private retreat

Marathon house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 15 minutes

Price per night from

$166

1 / 22

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

$236

1 / 13

P90 ~

Marathon house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$280

1 / 18

Gulf View Place w/ Dock, Pool, Kayaks, Sandy Shore

Marathon house

4 bedrooms / 4 bathrooms / sleeps 10

“Awsomely relaxing yet centrally located for easy day trips.” Very clean and nicely equipped with everything needed for a relaxing and comfortable at home feel vacation. Lots of room for family reunions. Centrally located in the Keys so day trips eithe

Price per night from

$429

1 / 27

New, Luxury 4/3 Single Family Home w/Pool , 40 ft BoatDock, short walk to Beach

Marathon Shores house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 54 minutes

Price per night from

$398

1 / 36

P02 Southern Hospitality

Marathon house

5 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$358

1 / 38

Vaca Cove - Open Water, Protected Dockage and Great Pool, Jan, Feb Specials!!!

Marathon house

4 bedrooms / 3 bathrooms / sleeps 10

“The Perfect Vacation!” The house was perfect for three families. The nice having a toast, coffee pot, blener and every thing we needed. The dock was perfect for our 25' boat. The kids loved the pool. The owners were there and were some of the kind

Price per night from

$451

1 / 22

P85 ~ Smooth Sailing - Tropical Single Family, pool home

Marathon house

2 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$215

1 / 17

P50 - Beach Bums

Marathon house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$301

1 / 25

Waterfront fun and funky , Beautiful Duck Key

Duck Key condo

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$176

1 / 26

Key Colony Beach Tropical Pool Home-Booking for Spring/Summer & Winter Holidays

Key Colony Beach house

3 bedrooms / 2 bathrooms / sleeps 9

“You will love this Home” We have stayed in this beautiful home for the last 5 winters. It has everything needed to make your stay relaxing and enjoyable. The home has a large well stocked kitchen, large flatscreen TV, comfortable furniture and we

Responds fast! avg. 27 minutes

Price per night from

$386

1 / 25

Waterfront Hideaway

Marathon Shores house

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$201

1 / 25

P01 ~ Sun Lovers Paradise! 3 bed/3.5 bath pool home near Sombrero Beach

Marathon house

3 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$308

1 / 49

The Beach Hut

Marathon Shores condo

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 32 minutes

Price per night from

$166

1 / 11

FALL ESCAPE, $275/night + cleaning & tax, Breathtaking Views, Private, Tranquil

Marathon house

4 bedrooms / 4 bathrooms / sleeps 10

“We thoroughly enjoyed our stay.” My wife and I would highly recommend The Sunrise Getaway House in Marathon. The accomodations were everything we wanted in our trip and more. The location was excellant and the view fantastic! We also found the coop

Price per night from

$430

1 / 76

Island Time 2 (half of duplex)

Big Pine Key house

3 bedrooms / 1 bathroom / sleeps 6

Price per night from

$94

1 / 16

Our Island Thing

Big Pine Key house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$201

1 / 16

"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 24 minutes

Price per night from

$394

1 / 45

Florida Keys Fisherman and Divers Paradise

Big Pine Key house

4 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$251

1 / 28

Gulf front fishing fun

Duck Key house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$315

1 / 13

Keys Cove House 8

Marathon Shores house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 1 hour 13 minutes

Price per night from

$501

1 / 53
Viewing 38 of 331
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