Search Vacation Homes in Long Key

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

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, (159)
"Clean extremely well cared for resort and accommodation, but not really the area we wanted. Expected to have bars restaurants close by but had to drive . Worked well for trips out to key West and local state parks. Pool was clean and empty. Enjoyed the free kayaks. Beds comfy and perfect if self catering. "
The price is SAR 571
SAR 1,175 total
includes taxes & fees
29 Apr - 30 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, (87)
"Very nice, lovely stay. Backyard is very relaxing, house is just right size. Close to everywhere we wanted to go. Bridge is walking distance. Has about anything you need to start your stay. "
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, (169)
"Beautiful place in the keys, and felt larger than the photos showed. Owner is very communicative! "
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

10.0 out of 10, Exceptional, (81)
"If you are lucky enough to find an opening for this house, just book it.The house and property are truly exceptional. Everything is thoughtfully labeled in the house, which is really handy when you just want to know what light switch turns on which light! The kitchen and bathrooms are VERY well stocked.The canal out back is very nice and my kids actually caught some cool fish out there. Manatees came to visit there are well. We loved the kayaks and paddle boards. The home is over 100 years old...
Oceanfront 165ft beach-Dock-Heated pool-4K sq.ft 4 bed/5 bath-Next avail 5.17.25

LAST MINUTE SPECIAL! May 10-17th 1950 + the fees!!!

9.6 out of 10, Exceptional, (120)
"House was clean, pool was great, location fabulous."
LAST MINUTE SPECIAL! May 10-17th 1950 + the fees!!!

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, (67)
"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, (111)
"Love Chausie and her properties! Top notch! "
5 bedroom - Deep Dockage & Heated Pool in Islamorada.

Coral Lagoon #13: Pool, Water Views, Both Gulf & Atlantic Access via Vaca Cut

10.0 out of 10, Exceptional, (254)
"I took my sons fishing in Marathon and wanted a nice place to stay. This house was perfect - clean, convenient, and comfortable. I would stay there again and highly recommend it. "
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

10.0 out of 10, Exceptional, (1)
"Great vacation spot. The unit was just as described and the host was super responsive. Any questions we had were addressed right away . Really could not ask for more. The access to the ocean was excellent, beds were comfortable, lots of towels, and updated appliances. Will most definitely be returning for another visit. Thank you. "
Home in Marathon w/ boat lift

Luxury Waterfront Oasis w Heated Pool and 50' Dock

9.8 out of 10, Exceptional, (28)
"We had a wonderful stay, however it was unfortunate that there were no TVs in two of the bedrooms. It’s important when you travel with other couples to be able to have your own “space“ and not having TV available in two of the bedrooms was disappointing. "
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, (31)
"This is a great spot if you’re coming to the keys. The location made it easy for day trips to visit other keys. The communication with the property manager was quick and easy. The location was clean and we enjoyed spending time on the outside patio watching the sunrise. The beds were comfy, the WiFi was fast and we loved being able to stream Netflix and Disney at night. It’s also walking distance to restaurants and the marina. Highly recommend this place for a great getaway! "
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, (148)
"The pool—the tiki hut—and the access to water was exactly what we wanted. The icemaker was icing on the cake! All beds are kings—and each has its own bathroom. Perfect! We are coming back for sure!"
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, (73)
"Peaceful spot at the end of a short street. Such attention to detail by the owner with everything you could need. The beds are super comfy as is the huge cosy sofa in the lounge. A fabulous week in a fabulous house. Thank you. "
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

Oceanfront Estate with Private 350 foot Pier, Heated Pool, Pet Friendly

9.4 out of 10, Exceptional, (93)
"Would definitely stay here again. Absolutely peaceful and amazing and exactly what we needed! JP was extremely helpful, friendly and amazing as well. Great place "
Oceanfront Estate with Private 350 foot Pier, Heated Pool, Pet Friendly
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.
Don't see what you're looking for?
See all available properties in Long Key
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Long Key

Skipjack Resort & Marina

3.0 star property
8.6 out of 10, Excellent, (1179)
"Incredibl"
The price is SAR 822
SAR 1,059 total
includes taxes & fees
29 Apr - 30 Apr
Skipjack Resort & Marina

Breezy Palms Resort

2.5 star property
8.6 out of 10, Excellent, (460)
"Expedia let me down. I ordered a room with two beds, and when we arrived, they gave me a room with a king bed. We are two hetero men on a fishing trip, and we were not really wanting to share a bed. BP blamed it on Expedia and said they couldn't give me a different room and said they didn't have another room with two beds to give us anyway. They did give us a roll-away bed, but the couch was more comfortable! We toughed it out in the King bad, but that was a bad start to the stay! "
The price is SAR 420
SAR 666 total
includes taxes & fees
4 May - 5 May
Breezy Palms Resort

Yacht Haven Marina

3.5 star property
9.8 out of 10, Exceptional, (138)
"Perfect location, perfect accommodations, fun place to stay"
The price is SAR 559
SAR 1,098 total
includes taxes & fees
4 May - 5 May
Yacht Haven Marina
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.