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Compare 1681 Vacation Homes in Long Key with updated reviews, rates, and availability.

Aqua Lodge Rentals At Coconut Cay

3.5 star property
9.6 out of 10, Exceptional, (155)
"Truly enjoyed our time in such a unique experience. "
The price is SAR 740
SAR 1,384 total
includes taxes & fees
8 Apr - 9 Apr
Aqua Lodge Rentals At Coconut Cay

Dragonfly Lite – A tropical oasis with your own heated saltwater pool to enjoy!

10.0 out of 10, Exceptional, (84)
"This was our first visit to the Keys and we were very pleased. The house is cozy and clean, and the outdoor pool area is phenomenal. Jerry and Lynn were wonderful hosts. The only bad part of the trip was returning to central Illinois weather. "
Dragonfly Lite – A tropical oasis with your own heated saltwater pool to enjoy!

Coral Lagoon Single Family Home 3bed/2.5bath with 40' Boat Slip w/ Power + Water

9.8 out of 10, Exceptional, (93)
"We were very pleased with this house - very clean and comfortable! It will be even better when the canal construction fencing is down and the use of the canal is restored -- we plan to return, maybe with our boat next time! "
Coral Lagoon Single Family Home 3bed/2.5bath with 40' Boat Slip w/ Power + Water

Best Deals in Duck Key . 2 Bedroom /2 Bath w/40' 'Dock, Trailer Storage Incl,

10.0 out of 10, Exceptional, (167)
"We all LOVED this place! It was simply perfect in every way, so Keys. Great location and the house was clean, so nicely decorated and just easy. Would totally stay here again anytime. "
Best Deals in Duck Key . 2 Bedroom /2 Bath w/40' 'Dock, Trailer Storage Incl,

COZY FAMILY HOME-POOL-HOTTUB -5 minute drive to sombrero beach-private property

10.0 out of 10, Exceptional, (34)
"Everything in the listing was completely accurate. Halfway point in the Keys. The home was very clean. Air Conditioning was spot on. We used the pool/hottub a lot. Surprised how much we used the hot tub as almost every day it was clear and hot. Although it didn’t bother us, the home is located in the direct path of a variety of planes jets and helicopters landing at Airport nearby. Noise was quite loud and may scare some dogs. Our Morkie had no issues. Definitely would rent property...
COZY FAMILY HOME-POOL-HOTTUB -5 minute drive to sombrero beach-private property

Oceanfront 165ft beach-Dock-Heated pool-4K sq.ft 4 bed/5 bath-Next avail 5.17.25

9.8 out of 10, Exceptional, (80)
"Everything just great except need better vaccum"
Oceanfront 165ft beach-Dock-Heated pool-4K sq.ft 4 bed/5 bath-Next avail 5.17.25

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

9.6 out of 10, Exceptional, (118)
"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

VR65 Beach Nuts | 4 Bed, 2 Bath Next to Sombrero Beach

9.6 out of 10, Exceptional, (46)
"Overall it was good. They could use more cooking bowls and sharper knives"
VR65 Beach Nuts | 4 Bed, 2 Bath Next to Sombrero Beach

Spacious Waterfront Home on a Direct Ocean Access Canal with a Chilled Pool

9.6 out of 10, Exceptional, (66)
"We chose this location due to how easy it was for us to access the ocean. The home has all the necessities, including, a big plus -- an outside ice maker and freezer. Very boater friendly - with nice neighbors. Sadly the weather did not cooperate the week we chose, giving us 25-33 mph winds, causing us to leave the boat on the trailer for 2 days. We have never experienced this type weather down in the Keys. It was even too chilly to swim in the pool, and some of the area around US1 near Florida...
Spacious Waterfront Home on a Direct Ocean Access Canal with a Chilled Pool

5 bedroom - Deep Dockage & Heated Pool in Islamorada.

10.0 out of 10, Exceptional, (110)
"This is our 2nd stay at this amazing home. Everything was perfect! This vacation rental has everything you could need for a fabulous stay in Islamorada!!! Excellent location for dining and well as a quick boat ride out to the sandbar. Our teens spent hours catching fish from the dock! Periodic visits from the local manatees was spectacular. We can’t wait to return to paradise next year!"
5 bedroom - Deep Dockage & Heated Pool in Islamorada.

🌴Beach, Pool, Dock,Boating, and Golfing Paradise!!🌴Pets Welcomed!

10.0 out of 10, Exceptional, (45)
"Great week in the Keys! This property has amazing outdoor space! Great fishing off the dock, easy access to Sisters Creek and the Atlantic. The pool area is perfect and well kept. Very quiet and private neighborhood and close to everything, restaurants, grocery store, and beach. The house is well equipped and has COLD A/C, it is a bit dated but suited our family and friends just fine. We are outside people and just need a place to shower and recoup for the next day.. We would definitely stay...
🌴Beach, Pool, Dock,Boating, and Golfing Paradise!!🌴Pets Welcomed!

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

Bikini Bottom - 3 Bedroom Home Canal With Boat Lift - Rental Lic# VACA-23-244

9.8 out of 10, Exceptional, (17)
"Stayed at this wonderful relaxing place with our best friends. We were able to relax, shop, visit throughout the keys then come back at the end of the day to rest and rejuvenate. John, the owner was very good at supplying us with all the details needed to access the VRBO along with info running appliances as well as what to do at check out. Thank you for allowing us to stay at your beautiful place.The Lillies"
Bikini Bottom - 3 Bedroom Home Canal With Boat Lift - Rental Lic# VACA-23-244

Home in Marathon w/ boat lift

Home in Marathon w/ boat lift

Luxury Waterfront Oasis w Heated Pool and 50' Dock

10.0 out of 10, Exceptional, (26)
"Our family had an absolutely wonderful stay at this fantastic property! From the moment we arrived, we were impressed by how clean, spacious, and well-equipped the home was. It was the perfect size for our group, with plenty of room for the kids to play and the adults to relax. The kitchen had everything we needed to cook meals together, which was a huge plus for our family. The beds were super comfortable, and the living areas were cozy and inviting—perfect for our movie nights. The outdoor...
Luxury Waterfront Oasis w Heated Pool and 50' Dock

KCB-access Private Cabana Club, Dock on Canal, PET Friendly, Pickle ball courts

9.4 out of 10, Exceptional, (79)
"Weather was great! Answered all my questions quickly"
KCB-access Private Cabana Club, Dock on Canal, PET Friendly, Pickle ball courts

Manatee Bay: Escape to this 2BR Duck Key Villa, Private Patio, Dip Pool & Easy Access to Marathon

9.8 out of 10, Exceptional, (28)
"Duck Key was beautiful and the perfect location. The house was clean and had everything we needed for our stay! Will definitely be back"
Manatee Bay: Escape to this 2BR Duck Key Villa, Private Patio, Dip Pool & Easy Access to Marathon

Open Water views, 100' dock Private Pool Ice machine DIRECT ACCESS open water

10.0 out of 10, Exceptional, (147)
"Pool and hot tube was great Househad everything you need for a long stay "
Open Water views, 100' dock Private Pool Ice machine DIRECT ACCESS open water

Don't Miss This! Deep Water Canal, Swimspa Pool, Kayaks, Walk to Tiki Bars!!

10.0 out of 10, Exceptional, (71)
"We had a wonderful time during our stay in the Florida Keys! The home and adjacent canal lot were spacious, comfortable, and very inviting. We completely recommend staying at Kathy's property!"
Don't Miss This! Deep Water Canal, Swimspa Pool, Kayaks, Walk to Tiki Bars!!

Beach House, Waterfront, Sombrero Beach, Florida Keys Rental, Private Pool, Dock

10.0 out of 10, Exceptional, (17)
"This property was amazing. The kids had plenty to do at the house and it was only a short walk to the beach. Perfect location. Can’t wait to come back again!"
Beach House, Waterfront, Sombrero Beach, Florida Keys Rental, Private Pool, Dock
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 property types in Long Key

Skipjack Resort & Marina

3.0 star property
8.6 out of 10, Excellent, (1170)
"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 SAR 1,010
SAR 1,271 total
includes taxes & fees
8 Apr - 9 Apr
Skipjack Resort & Marina

Breezy Palms Resort

2.5 star property
8.6 out of 10, Excellent, (441)
"Best motel we’ve stayed at in Keys! Outstanding!"
The price is SAR 401
SAR 645 total
includes taxes & fees
14 Apr - 15 Apr
Breezy Palms Resort

Tropical Cottages

3.0 star property
8.4 out of 10, Very Good, (796)
"Nice, clean and cute little private bungalows. We were visiting friends in the area and this was the perfect location. "
The price is SAR 432
SAR 486 total
includes taxes & fees
9 Apr - 10 Apr
Tropical Cottages
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.