Vacation Rentals in Islamorada, Florida
Islamorada, Florida Vacation Rentals and Tourism
For your next vacation, head south and discover what the Florida Keys have to offer by reserving your Islamorada lodging through Vacation Rentals.com. Islamorada, Florida Keys rentals are as conveniently located to Islamorada attractions as Islamorada hotels, but they provide you with something Islamorada hotels cannot - a sense of being at home. Live like a local in one of these many house rentals; Islamorada deserves your undivided attention after all! Truly become a part of this fisherman's paradise.
- What more help planning your vacation? Read our full Islamorada Travel Guide!
This colorful series of keys, given the Spanish name "purple island" by early Spanish explorers, has its own pace and way of life. The strict ordinances against over-development ensure that you'll experience a destination much different from the many other areas of Florida's coast. Eschewing formula retail chains, Islamorada condo rentals fit the "lack of a façade" that's the defining characteristic of the area.
So, if you're ready to trade strip malls for some of the best sports fishing in the country, check out one of the many homes for rent in Islamorada for your next vacation. These Islamorada Keys house rentals provide all the comforts of home, including laundry machines, Wi-Fi Internet access, big-screen televisions, and fully-furnished kitchens, so you can cook what you catch rather than spending all of your money in Islamorada restaurants.
Give more than just a glance to Islamorada accommodations; Florida Keys vacation rentals are best researched on Vacation Rentals.com. Choose an Islamorada vacation rental as your next home in Islamorada.
There's no better place to relax than at Islamorada. It's time you treat yourself to a vacation away from it all, staying in a luxurious but affordable Islamorada vacation rental! Among all the beaches and boat rides, don't let your budget get in the way of having fun and feeling stress-free. With great deals and discounts on Islamorada vacation rentals, you can choose from any of our low-price high value condos, town homes or beach houses. Our spacious, yet budget friendly options are perfect for a large group or for you and that special someone to enjoy a luxurious and affordable Islamorada rental home. So don't let money stop you from enjoying the sunsets, electric boat rides and relaxing on your Islamorada vacation, because our list of comfy, cheap Islamorada vacation rentals has your great deal already taken care of.
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Islamorada things to do
History of Diving Museum
If your visiting the keys and your a diver, which I would assume at least half of the people who visit the keys are then this is a must stop location. The...read more
Anne's Beach
The water is clear blue, warm, shallow enough to tread through for a good length, but I can imagine the parking can get terrible, and there really isn't...read more
Robbie's of Islamorada
Visited again 2 years later and it is still the same. Robbies is the best value in the keys that I have found. This time we stopped for souvenir...read more
Theater of the Sea
I was recently there for a rehearsal dinner. They rented out the park. Great easy walk through exhibits of marine mammals, fish, birds, and reptiles. What...read more
Islamorada Dive Center
While the Islamorada Dive Center is geared toward scuba divers, they do take along snorkelers to the dive sites. The staff is friendly and provides guidance...read more
True Island Adventures
We had a great time with Captain Hagood. I let him know in advance what kind of trip we were interested in, and he made sure our family - two adults and two...read more
Otherside Boardsports LLC
I went down to Islamorada to get married. During our week there, my fiance and I really wanted to get some kiteboarding lessons. We had set up some a time...read more
Backcountry Cowboy Outfitters
Very helpful and polite. Their store is filled with interesting stuff. They drop you off at different locations to go on your kayak trip. Pick up the...read more
A1A Watersports & Boat Rentals
Had the greatest time on the Jetski eco tour. I've been on many jet skis and never had a fun guide as great as Joe! Insist on that guy! So much fun through...read more
Indian Key State Historic Site
Today it's largely overgrown, though the state has maintained a few of the "streets" and there are some plaques detailing the events surrounding the...read more
Indian Key
luis gave the history of Indian key so I won't repeat it. Snorkeling here is one of the most peaceful ,beautiful things you could possibly do. We had a...read more
Islamorada Boat Tours
We went on a sunset cruise on the Maddie Sue. It's a newer and very clean pontoon boat with a radio, rest room and coolers to store any drinks you bring on...read more
Bump & Jump Boat Rental
I will start by saying that one of the flagged reviews is TOTALLY legit because I too rented the boat that had a seat which was held up by TAPE! I have...read more
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$300 off = $1,700 per week
- bedrooms 3
- community Bay Harbour
- rental type Condo
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- sleeps 6
- baths 2½
- rates (USD)
$1,700
- $2,400
/wk
-
$250 off = $900 per week
- bedrooms 2
- community Islamorada
- rental type Condo
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- sleeps 4
- baths 2
- rates (USD)
$775
- $1,550
/wk
-
$300 off = $1,500 per week
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Welcome Gifts
($40)
- bedrooms 2
- community Bay Harbour
- rental type Condo
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- sleeps 6
- baths 2½
- rates (USD)
$1
- $1
/nt
$1,400 - $2,000 /wk
-
$200 off = $650 per week
- bedrooms 1
- community Summer Sea
- rental type Condo
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- sleeps 4
- baths 1
- rates (USD)
$650
- $850
/wk
-
$250 off = $600 per week
- bedrooms 2
- community Futura Yacht Club
- rental type Condo
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- sleeps 6
- baths 2
- rates (USD)
$600
- $850
/wk
$2,200 - $3,200 /mth
-
15% off = $3,230 per month
- bedrooms 3
- community Islamorada
- rental type House
- sleeps 10
- baths 2
- rates (USD)
$1
- $1
/nt
$1 - $1 /wk
$3,000 - $5,000 /mth
-
10% off = $1,980 per month
- bedrooms 2
- community Islamorada South
- rental type Townhome
- sleeps 6
- baths 2
- rates (USD) $2,200 - $2,500 /mth
-
$300 off = $3,500 per month
- bedrooms 3
- community
- rental type House
- sleeps 8
- baths 3
- rates (USD) $3,800 - $4,500 /mth
-
$1,000 off = $3,500 per week
- bedrooms 5
- community
- rental type House
- sleeps 14
- baths 5
- rates (USD)
$4,000
- $6,500
/wk
-
20% off = $720 per week
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Fresh Fl Keys Fish
($100)
- bedrooms 2
- community PlantationKeyColony
- rental type House
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- sleeps 5
- baths 1
- rates (USD)
$750
- $1,000
/wk
$1,500 - $3,000 /mth
-
$200 off = $725 per week
- bedrooms 2
- community Futura Yacht Club
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$825
- $1,125
/wk
$3,000 - $3,200 /mth
-
$200 off = $1,225 per week
- bedrooms 3
- community Futura Yacht Club
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$1,025
- $1,425
/wk
$3,400 - $3,600 /mth
-
$200 off = $2,300 per week
- bedrooms 4
- community
- rental type House
- sleeps 8
- baths 3
- rates (USD)
$2,300
- $2,700
/wk
-
$200 off = $1,225 per week
- bedrooms 2
- community
- rental type Townhome
- sleeps 6
- baths 2½
- rates (USD)
$1,125
- $1,525
/wk
$3,500 - $4,500 /mth
-
10% off = $625 per week
- bedrooms 1
- community Coco Plum Terraces
- rental type Studio
- sleeps 3
- baths 1
- rates (USD)
$90
- $140
/nt
$595 - $895 /wk
$1,900 - $2,800 /mth
- bedrooms 2
- community Seagulls Condos
- rental type Condo
- sleeps 4
- baths 2
- rates (USD)
$800
- $1,250
/wk
- bedrooms 4
- community Ocean Shores Estates
- rental type House
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- sleeps 12
- baths 3
- rates (USD)
$300
- $500
/nt
$2,100 - $3,000 /wk
$6,500 - $9,700 /mth
- bedrooms 4
- community Safety Harbor
- rental type House
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- sleeps 8
- baths 4
- rates (USD) $10,000 - $12,000 /mth
- bedrooms 3
- community
- rental type House
- sleeps 6
- baths 2½
- rates (USD)
$425
- $500
/nt
$2,975 - $3,500 /wk
$8,925 - $10,500 /mth
- bedrooms 2
- community
- rental type Townhome
- sleeps 6
- baths 2½
- rates (USD)
$1,200
- $1,800
/wk
$4,000 - $6,000 /mth
- bedrooms 2
- community
- rental type Condo
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- sleeps 6
- baths 2
- rates (USD)
$1,200
- $1,400
/wk
$1,900 - $2,900 /mth
- bedrooms 3
- community White Marlin
- rental type House
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- sleeps 6
- baths 2
- rates (USD) $8,000 - $12,000 /mth
- bedrooms 3
- community
- rental type House
- sleeps 6
- baths 3
- rates (USD) $6,000 - $6,000 /mth
- bedrooms 3
- community Islamorada
- rental type House
owner badge
- sleeps 6
- baths 3
- rates (USD)
$1,000
- $1,500
/wk
$4,000 - $5,600 /mth
- bedrooms 3
- community Plantation KeyColony
- rental type House
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- sleeps 8
- baths 3
- rates (USD) $2,999 - $3,999 /mth
- bedrooms 1
- community
- rental type House
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- sleeps 2
- baths 1
- rates (USD)
$250
- $300
/nt
$1,700 - $2,050 /wk
- bedrooms 1
- community Summer Sea
- rental type Condo
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- sleeps 4
- baths 1
- rates (USD)
$795
- $1,095
/wk
$2,995 - $3,495 /mth
- bedrooms 8
- community
- rental type House
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- sleeps 14
- baths 5½
- rates (USD)
$3,750
- $9,500
/wk
- bedrooms 3
- community
- rental type Villa
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- sleeps 8
- baths 2
- rates (USD)
$1,650
- $1,850
/wk
- bedrooms 2
- community Futura Yacht Club
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$600
- $850
/wk
- bedrooms 3
- community Executive Bay Club
- rental type Townhome
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- sleeps 6
- baths 2
- rates (USD)
$180
- $220
/nt
$1,150 - $1,395 /wk
$2,400 - $3,600 /mth
- bedrooms 5
- community
- rental type House
- sleeps 10
- baths 5½
- rates (USD) $18,000 - $24,000 /mth
- bedrooms 4
- community
- rental type House
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- sleeps 10
- baths 3
- rates (USD)
$2,500
- $3,500
/wk
- bedrooms 4
- community
- rental type House
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- sleeps 10
- baths 4½
- rates (USD)
$4,000
- $6,500
/wk
- bedrooms 3
- community
- rental type House
- sleeps 6
- baths 2
- rates (USD)
$2,500
- $2,500
/wk
- bedrooms 4
- community
- rental type House
- sleeps 8
- baths 4½
- rates (USD)
$4,500
- $5,000
/wk
- bedrooms 3
- community
- rental type House
- sleeps 8
- baths 3
- rates (USD)
$4,000
- $4,000
/wk
- bedrooms 5
- community
- rental type House
- sleeps 10
- baths 6
- rates (USD)
$8,950
- $8,950
/wk
- bedrooms 3
- community
- rental type House
- sleeps 8
- baths 3
- rates (USD)
$4,000
- $4,000
/wk
$16,000 - $16,000 /mth
- bedrooms 3
- community
- rental type House
- sleeps 6
- baths 3½
- rates (USD)
$6,000
- $6,000
/wk
- bedrooms 3
- community
- rental type House
- sleeps 6
- baths 2
- rates (USD)
$3,000
- $3,000
/wk
- bedrooms 4
- community Venetian Shores
- rental type House
- sleeps 10
- baths 4
- rates (USD) $6,000 - $6,000 /mth
- bedrooms 3
- community Bay Harbour
- rental type Condo
owner badge
- sleeps 8
- baths 2½
- rates (USD)
$1,800
- $2,500
/wk
$4,000 - $5,500 /mth
- bedrooms 4
- community
- rental type House
- sleeps 8
- baths 4
- rates (USD)
$4,300
- $4,800
/wk
- bedrooms 2
- community Holiday House
- rental type House
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- sleeps 4
- baths 1
- rates (USD)
$895
- $1,095
/wk
- bedrooms 2
- community Holiday House
- rental type Villa
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- sleeps 6
- baths 2
- rates (USD)
$1,295
- $1,495
/wk
- bedrooms 2
- community
- rental type House
- sleeps 6
- baths 2
- rates (USD)
$1,300
- $1,500
/wk
$3,400 - $3,900 /mth
- bedrooms 2
- community
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$800
- $1,350
/wk
$2,500 - $3,500 /mth
- bedrooms 6
- community
- rental type House
- sleeps 14
- baths 6
- rates (USD)
$5,500
- $8,500
/wk
$20,000 - $24,000 /mth
- bedrooms 4
- community
- rental type House
- sleeps 12
- baths 4½
- rates (USD)
$4,500
- $5,800
/wk
$13,500 - $17,400 /mth
- bedrooms 2
- community Futura Yacht Club
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$800
- $1,100
/wk
$2,400 - $3,200 /mth
- bedrooms 2
- community
- rental type Apartment
owner badge
- sleeps 6
- baths 1
- rates (USD)
$140
- $140
/nt
$840 - $840 /wk
$2,520 - $2,520 /mth
- bedrooms 3
- community Islamorada
- rental type House
- sleeps 6
- baths 2
- rates (USD)
$1,000
- $1,300
/wk
$2,500 - $3,950 /mth
- bedrooms 5
- community
- rental type House
- sleeps 10
- baths 5½
- rates (USD)
$6,000
- $6,000
/wk
- bedrooms 4
- community
- rental type House
- sleeps 8
- baths 3
- rates (USD)
$4,500
- $4,500
/wk
- bedrooms 4
- community
- rental type House
- sleeps 8
- baths 4
- rates (USD)
$6,500
- $6,500
/wk
- bedrooms 2
- community Executive Bay Club
- rental type Condo
- sleeps 8
- baths 2
- rates (USD) $3,000 - $3,000 /mth
- bedrooms 2
- community
- rental type House
- sleeps 5
- baths 2
- rates (USD)
$1,300
- $1,600
/wk
$4,500 - $6,000 /mth
- bedrooms 3
- community Toll Gate Shores
- rental type House
owner badge
- sleeps 6
- baths 3
- rates (USD)
$1,800
- $2,100
/wk
$5,500 - $6,000 /mth
- bedrooms 1
- community Sea Gulls Condo
- rental type Condo
- sleeps 4
- baths 1
- rates (USD)
$700
- $950
/wk
- bedrooms 3
- community Bay Harbour
- rental type Condo
- sleeps 6
- baths 2½
- rates (USD)
$2,100
- $2,500
/wk
$6,500 - $6,500 /mth
- bedrooms 4
- community
- rental type House
- sleeps 8
- baths 3
- rates (USD)
$3,800
- $4,800
/wk
$11,400 - $14,400 /mth
- bedrooms 2
- community Plantation Key Colon
- rental type House
- sleeps 6
- baths 3
- rates (USD)
$825
- $1,225
/wk
$2,800 - $2,925 /mth
- bedrooms 3
- community
- rental type House
owner badge
- sleeps 12
- baths 3½
- rates (USD)
$1,950
- $4,000
/wk
$6,000 - $8,500 /mth
- bedrooms 1
- community
- rental type House
owner badge
- sleeps 2
- baths 1
- rates (USD)
$900
- $1,500
/wk
$3,500 - $5,000 /mth
- bedrooms 3
- community
- rental type House
- sleeps 9
- baths 2
- rates (USD)
$600
- $600
/nt
$2,500 - $2,500 /wk
$9,000 - $9,000 /mth
- bedrooms 1
- community Holiday House
- rental type Condo
owner badge
- sleeps 4
- baths 2
- rates (USD)
$1,200
- $1,300
/wk
$3,000 - $4,000 /mth
- bedrooms 3
- community
- rental type House
- sleeps 8
- baths 2
- rates (USD)
$1,200
- $2,000
/wk
- bedrooms 2
- community Summer Sea Condos
- rental type Condo
- sleeps 4
- baths 2
- rates (USD) $2,800 - $3,200 /mth
- bedrooms 2
- community
- rental type Cottage
- sleeps 5
- baths 1
- rates (USD) $3,500 - $4,000 /mth
- bedrooms 2
- community Holiday House
- rental type Villa
owner badge
- sleeps 8
- baths 2
- rates (USD)
$1,100
- $1,300
/wk
- bedrooms 2
- community
- rental type House
- sleeps 6
- baths 2
- rates (USD) $2,000 - $2,500 /mth
- bedrooms 3
- community
- rental type House
- sleeps 8
- baths 3
- rates (USD)
$1,500
- $2,000
/wk
$2,200 - $3,800 /mth
- bedrooms 1
- community Seagulls Condos
- rental type Condo
owner badge
- sleeps 3
- baths 1
- rates (USD)
$700
- $900
/wk
$1,200 - $3,400 /mth
- bedrooms 1
- community Summer Sea
- rental type Condo
- sleeps 4
- baths 1
- rates (USD)
$850
- $950
/wk
$2,800 - $2,800 /mth
- bedrooms 3
- community
- rental type House
owner badge
- sleeps 5
- baths 2
- rates (USD)
$2,500
- $3,000
/wk
$6,500 - $7,000 /mth
- bedrooms 3
- community Executive Bay Club
- rental type Townhome
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- sleeps 8
- baths 2
- rates (USD) $2,400 - $2,800 /mth
- bedrooms 2
- community Islamorada
- rental type Townhome
- sleeps 5
- baths 2
- rates (USD) $2,500 - $3,000 /mth
- bedrooms 4
- community
- rental type House
owner badge
- sleeps 10
- baths 4
- rates (USD)
$6,000
- $6,000
/wk
$19,000 - $19,000 /mth
- bedrooms 2
- community Lower Matecumbe
- rental type House
- sleeps 4
- baths 2
- rates (USD) $3,300 - $3,300 /mth
- bedrooms 4
- community
- rental type House
- sleeps 8
- baths 3
- rates (USD)
$2,500
- $2,500
/wk
$7,000 - $8,000 /mth
- bedrooms 3
- community Bay Harbour Condo
- rental type Condo
- sleeps 8
- baths 2½
- rates (USD) $6,000 - $8,200 /mth
- bedrooms 3
- community Millionaires Row
- rental type Cottage
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- sleeps 8
- baths 3
- rates (USD)
$275
- $500
/nt
$1,975 - $3,500 /wk
$5,800 - $7,800 /mth
- bedrooms 1
- community Summer Sea Condo
- rental type Condo
- sleeps 4
- baths 1
- rates (USD)
$750
- $800
/wk
$2,900 - $3,200 /mth
- bedrooms 3
- community Ocean Harbour
- rental type Condo
- sleeps 8
- baths 2½
- rates (USD) $7,000 - $8,000 /mth
- bedrooms 2
- community
- rental type Cottage
- sleeps 4
- baths 1½
- rates (USD)
$209
- $259
/nt
$1,299 - $1,599 /wk
- bedrooms 2
- community
- rental type Cottage
- sleeps 4
- baths 1
- rates (USD)
$209
- $259
/nt
$1,299 - $1,599 /wk
- bedrooms 1
- community Matecumbe Sandy Cove
- rental type Condo
- sleeps 4
- baths 1
- rates (USD)
$800
- $800
/wk
$2,500 - $2,500 /mth
- bedrooms 4
- community
- rental type House
owner badge
- sleeps 12
- baths 3
- rates (USD) $7,900 - $8,500 /mth
- bedrooms 3
- community
- rental type Condo
- sleeps 8
- baths 2½
- rates (USD)
$3,000
- $4,000
/wk
$5,000 - $10,000 /mth
- bedrooms 3
- community Bay Harbour
- rental type Condo
- sleeps 8
- baths 2½
- rates (USD)
$2,000
- $2,500
/wk
$5,500 - $6,500 /mth
- bedrooms 6
- community High Point
- rental type House
- sleeps 10
- baths 4½
- rates (USD) $7,500 - $10,000 /mth
- bedrooms 3
- community
- rental type House
- sleeps 8
- baths 3
- rates (USD) $12,000 - $12,000 /mth
- bedrooms 1
- community Windley Key MHP
- rental type House
- sleeps 4
- baths 1
- rates (USD) $1,600 - $1,600 /mth
- bedrooms 2
- community Port Antigua
- rental type House
- sleeps 6
- baths 2
- rates (USD) $5,000 - $6,000 /mth
- bedrooms 3
- community Port Antigua
- rental type House
- sleeps 8
- baths 2
- rates (USD)
$1,515
- $2,025
/wk
$4,950 - $5,850 /mth
- bedrooms 3
- community Port Antigua
- rental type House
- sleeps 8
- baths 3
- rates (USD) $2,500 - $3,000 /mth
- bedrooms 2
- community Islamorada
- rental type House
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- sleeps 4
- baths 1
- rates (USD) $2,500 - $2,500 /mth
- bedrooms 0
- community Summer Sea Condos
- rental type Studio
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- sleeps 4
- baths 1
- rates (USD)
$450
- $700
/wk
- bedrooms 2
- community Executive Bay Club
- rental type Townhome
- sleeps 6
- baths 2
- rates (USD) $2,500 - $2,500 /mth
- bedrooms 2
- community
- rental type Townhome
- sleeps 4
- baths 1½
- rates (USD)
$255
- $549
/nt
$1,275 - $2,745 /wk
$3,200 - $5,700 /mth
- bedrooms 2
- community Sea Gulls condos
- rental type Condo
- sleeps 5
- baths 2
- rates (USD)
$875
- $1,500
/wk
$3,000 - $4,400 /mth
- bedrooms 3
- community venetian shores
- rental type House
- sleeps 6
- baths 2
- rates (USD) $4,350 - $4,500 /mth
- bedrooms 2
- community Tavernier
- rental type House
- sleeps 9
- baths 2
- rates (USD) $2,000 - $4,500 /mth
- bedrooms 3
- community Port Antigua
- rental type House
- sleeps 6
- baths 3
- rates (USD) $4,400 - $4,900 /mth
- bedrooms 4
- community Venetian Shores
- rental type House
- sleeps 1
- baths 4
- rates (USD)
$3,500
- $4,500
/wk
$13,000 - $17,000 /mth
- bedrooms 7
- community
- rental type House
- sleeps 20
- baths 4
- rates (USD)
$850
- $6,500
/wk
- bedrooms 6
- community Venetian Shores
- rental type House
- sleeps 13
- baths 4½
- rates (USD)
$3,500
- $4,500
/wk
$6,500 - $8,500 /mth
- bedrooms 1
- community
- rental type House
- sleeps 6
- baths 1
- rates (USD)
$750
- $1,450
/wk
- bedrooms 2
- community
- rental type House
- sleeps 6
- baths 2
- rates (USD) $2,700 - $2,700 /mth
- bedrooms 3
- community Sandy Cove
- rental type Condo
- sleeps 6
- baths 3½
- rates (USD)
$1,650
- $1,800
/wk
- bedrooms 3
- community
- rental type House
- sleeps 10
- baths 2
- rates (USD) $1,500 - $7,500 /mth
- bedrooms 2
- community
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$900
- $1,300
/wk
- bedrooms 1
- community islamorada
- rental type Condo
- sleeps 2
- baths 1
- rates (USD)
$595
- $695
/wk
$1,750 - $2,250 /mth
- bedrooms 3
- community
- rental type House
- sleeps 8
- baths 3
- rates (USD) $5,000 - $6,000 /mth
- bedrooms 5
- community
- rental type House
- sleeps 8
- baths 4
- rates (USD)
$4,500
- $5,500
/wk
- bedrooms 3
- community White Marlin Beach
- rental type House
- sleeps 6
- baths 2
- rates (USD)
$2,600
- $2,900
/wk
- bedrooms 4
- community Venetian Shores
- rental type House
- sleeps 8
- baths 3
- rates (USD)
$2,500
- $3,500
/wk
$5,000 - $8,000 /mth
- bedrooms 2
- community
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$700
- $1,350
/wk
- bedrooms 0
- community
- rental type Studio
- sleeps 4
- baths 1
- rates (USD) $1,800 - $2,400 /mth
- bedrooms 2
- community Sea Gulls Condos
- rental type Condo
owner badge
- sleeps 4
- baths 2
- rates (USD)
$900
- $1,595
/wk
- bedrooms 3
- community
- rental type House
- sleeps 6
- baths 2
- rates (USD)
$1,650
- $2,000
/wk
$4,000 - $4,200 /mth
- bedrooms 5
- community
- rental type House
owner badge
- sleeps 10
- baths 3½
- rates (USD)
$2,500
- $3,100
/wk
$9,000 - $11,000 /mth





