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Check prices for these dates

In two weeks
20 Mar - 22 Mar
In two months
1 May - 3 May
In three months
29 May - 31 May
In four months
26 Jun - 28 Jun

Our top choices for Long Key vacation homes

Outdoor dining

Private Beach / Private overwater dock / Heated Pool / Mahi Key

Private Beach / Private overwater dock / Heated Pool / Mahi Key
Matecumbe
10.0 out of 10, Exceptional, (1 review)
"This property and the entire community was amazing. This was a fantastic vacation. One of the best we have had in years!"
United States
Gmac W.
The price is AED 9,014
AED 13,493 total
includes taxes & fees
14 Mar - 15 Mar
Private Beach / Private overwater dock / Heated Pool / Mahi Key
Property grounds

Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA

Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA
Duck Key
9.6 out of 10, Exceptional, (48 reviews)
"Clean property! Great views! Great communication with owner! Perfect location- close to marathon and key west! "
United States
candi b.
The price is AED 1,172
AED 2,534 total
includes taxes & fees
9 Mar - 10 Mar
Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA
Outdoor dining

Tiny Villa, Big Ocean Views| Breathtaking Sunsets

Tiny Villa, Big Ocean Views| Breathtaking Sunsets
Duck Key
10.0 out of 10, Exceptional, (15 reviews)
"Beautiful views. Very nice accommodations. Wonderfull location!"
United States
michael h.
The price is AED 1,153
AED 2,328 total
includes taxes & fees
9 Mar - 10 Mar
Tiny Villa, Big Ocean Views| Breathtaking Sunsets
Outdoor pool

SPECIAL-2 Bed 2.5 Bath Villa including Cabana Club membership

SPECIAL-2 Bed 2.5 Bath Villa including Cabana Club membership
Marathon
9.8 out of 10, Exceptional, (144 reviews)
"Great location and very neat place!"
United States
FERNANDO S.
The price is AED 1,282
AED 2,673 total
includes taxes & fees
12 Mar - 13 Mar
SPECIAL-2 Bed 2.5 Bath Villa including Cabana Club membership
Outdoor dining

Oceanfront Tiny Villa in the Heart of the FL Keys

Oceanfront Tiny Villa in the Heart of the FL Keys
Marathon
10.0 out of 10, Exceptional, (13 reviews)
"Would stay here again! Fast and responsive host. Beautiful views!"
United States
Carson F.
The price is AED 1,153
AED 2,376 total
includes taxes & fees
13 Mar - 14 Mar
Oceanfront Tiny Villa in the Heart of the FL Keys
TV

Villa 5020 on Duck Key Boat Slip Available - 2BD 2.5BA

Villa 5020 on Duck Key Boat Slip Available - 2BD 2.5BA
Duck Key
8.6 out of 10, Excellent, (11 reviews)
"Unit was very clean and had everything we needed"
United States
Vanessa L.
The price is AED 1,576
AED 3,044 total
includes taxes & fees
10 Mar - 11 Mar
Villa 5020 on Duck Key Boat Slip Available - 2BD 2.5BA
Outdoor dining

Villa 5023 on Duck Key Boat Slip Available - 2BD 1.5BA

Villa 5023 on Duck Key Boat Slip Available - 2BD 1.5BA
Duck Key
9.4 out of 10, Exceptional, (33 reviews)
"Perfect for our get away"
United States
Kelly H.
The price is AED 1,539
AED 2,999 total
includes taxes & fees
12 Mar - 13 Mar
Villa 5023 on Duck Key Boat Slip Available - 2BD 1.5BA
Exterior

Blue Waters Stay - 2BR 3BA Coastal Villa

Blue Waters Stay - 2BR 3BA Coastal Villa
Duck Key
9.0 out of 10, Wonderful, (2 reviews)
"Excellent host, great location, great amenities, tidy & reasonably clean. Our host, Ana, had a booklet which includes everything from A-Z about the accomodations & area. The location is perhaps the quietest key - one road in, one out. The place is tidy with many amenities. Note the villas are attached and you can hear your neighbors to some extent, especially the washer/dryers. We would have given 5-stars, except for the lack of attention to the cleanliness of some areas of the kitchen and...
United States
Sherianne H.
The price is AED 1,081
AED 2,397 total
includes taxes & fees
11 Mar - 12 Mar
Blue Waters Stay - 2BR 3BA Coastal Villa
Exterior

Charming 3-bedroom house featuring a heated private pool.

Charming 3-bedroom house featuring a heated private pool.
Duck Key
10.0 out of 10, Exceptional, (10 reviews)
"This villa exceeded our expectations. All the bedrooms have king size beds and there is a 3/4 bath on the first floor which was unexpected and perfect as all the couples had there own bathroom. Melissa was very fast to respond to some issues (smoke alarm in one of the bedrooms needed batteries) and maintenance was there within the hour. The pool was heated and very private. I would highly recommend this place to stay. "
United States
Melissa B.
Charming 3-bedroom house featuring a heated private pool.
Outdoor dining

Waterfront! 4 Bed/3 BA Townhome, 32FTDock, Cabana Club, Paddleboard, Beach Gear!

Waterfront! 4 Bed/3 BA Townhome, 32FTDock, Cabana Club, Paddleboard, Beach Gear!
Marathon
10.0 out of 10, Exceptional, (161 reviews)
"Awesome place on the canal. Great view, clean, and just about everything we needed was there. Other than needing a water hose down by the dock for washing the boat at the end of the day. Overall, couldn’t be happier with this place. Definitely would stay here again. "
United States
JD F.
The price is AED 2,615
AED 5,501 total
includes taxes & fees
9 Mar - 10 Mar
Waterfront! 4 Bed/3 BA Townhome, 32FTDock, Cabana Club, Paddleboard, Beach Gear!
Exterior

4 Bedroom 3 Bathroom Sanctuary Villa W/ Private Pool & 35ft dock upon request

4 Bedroom 3 Bathroom Sanctuary Villa W/ Private Pool & 35ft dock upon request
Duck Key
9.6 out of 10, Exceptional, (8 reviews)
"The villa is in a great location, and has a very private and secluded feeling to it when inside and around the pool. We had a great time, the villa met and exceeded or expectations, there were 6 of us staying there and the age ranges were from 27 to 64, we rented a charter boat out of marathon so the villa location was perfect.Thank you very much for such a great place to stay, we will try and stay here again if we come back down."
United States
Kevin J.
The price is AED 3,486
AED 6,165 total
includes taxes & fees
8 Mar - 9 Mar
4 Bedroom 3 Bathroom Sanctuary Villa W/ Private Pool & 35ft dock upon request
Outdoor dining

Lovely Water View! 3 Bed, 3 BA Townhome, Cabana Club: Oceanfront Beach, Pool!

Lovely Water View! 3 Bed, 3 BA Townhome, Cabana Club: Oceanfront Beach, Pool!
Marathon
6.0 out of 10, (1 review)
"Easy booking process and host was gracious and welcoming, available through duration of our stay.Unit: location was good, unit was clean when we arrived, easy to access with front door code, reasonably stocked bathrooms with necessities. Layout is exactly what we expected and gave our family of four plenty of space to spread out, probably more space than we needed but we had larger party at time of booking and several backed out semi-last minute. Living room furniture was tired and worn, patio...
United States
Stephanie B.
The price is AED 1,976
AED 4,694 total
includes taxes & fees
22 Mar - 23 Mar
Lovely Water View! 3 Bed, 3 BA Townhome, Cabana Club: Oceanfront Beach, Pool!
Pool

Piece of Paradise located at Hawks Cay in Duck Key

Piece of Paradise located at Hawks Cay in Duck Key
Duck Key
9.6 out of 10, Exceptional, (18 reviews)
"Amazing place. "
United States
Pilar G.
The price is AED 4,040
AED 5,437 total
includes taxes & fees
22 Mar - 23 Mar
Piece of Paradise located at Hawks Cay in Duck Key
Interior

Villa 7205 on Duck Key - 3 BR & 3 BA - Boat Slip available

Villa 7205 on Duck Key - 3 BR & 3 BA - Boat Slip available
Duck Key
The price is AED 3,302
AED 5,903 total
includes taxes & fees
19 Mar - 20 Mar
Villa 7205 on Duck Key - 3 BR & 3 BA - Boat Slip available
Exterior

Heated Pool, Views, Vaca Cut , Gulf & Atlantic Access. Availability Nov + Dec

Heated Pool, Views, Vaca Cut , Gulf & Atlantic Access. Availability Nov + Dec
Coral Lagoon
10.0 out of 10, Exceptional, (272 reviews)
"Excellent stay for a family."
United States
Sandra P.
The price is AED 1,636
AED 3,238 total
includes taxes & fees
10 Mar - 11 Mar
Heated Pool, Views, Vaca Cut , Gulf & Atlantic Access. Availability Nov + Dec
Terrace/patio

Charming 2-bedroom house in Marathon with pool

Charming 2-bedroom house in Marathon with pool
Marathon
8.0 out of 10, Very Good, (2 reviews)
"Great Home & Location & Enjoyable Stay! Thanks!"
United States
James J.
The price is AED 1,286
AED 3,028 total
includes taxes & fees
18 Mar - 19 Mar
Charming 2-bedroom house in Marathon with pool
Marina

Escape To Marathon in Large 4BR 3BA Canal Front Home Sleep 10 with Heated Pool

Escape To Marathon in Large 4BR 3BA Canal Front Home Sleep 10 with Heated Pool
Marathon
9.6 out of 10, Exceptional, (94 reviews)
"Had a wonderful time. Great location, private pool and everything you could think of. This trip it was just the two of us. This would be a great place for a family. 100% would come back and would recommend spending your vacation here. "
United States
Melissa L.
Escape To Marathon in Large 4BR 3BA Canal Front Home Sleep 10 with Heated Pool
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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Top Long Key Hotel Reviews

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

2/10 Terrible
"Overpriced for a view of the parking lot on the ground floor."
Peter 2-night trip
Posted 2 hours ago
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort