A pier with a boat rental sign, a colorful building, and a calm sea.

Long Key Vacation Rentals

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Long Key vacation homes

A round table set for two with a view of the ocean and palm trees.

1. Tiny Villa, Big Ocean Views| Breathtaking Sunsets

Tiny Villa, Big Ocean Views| Breathtaking Sunsets
Duck Key
10.0 out of 10, Exceptional, (24 reviews)
"This was without a doubt one of the nicest places we have ever stayed! Our hostess was PHENOMENAL and went above and beyond to be sure we were comfortable and had everything we needed for our stay. Literally the best vacation we’ve had!!!’ I suggest this place to everyone!"
United States
Stephanie
The price is CA $272
CA $698 total
includes taxes & fees
Nov 18 - Nov 19
Tiny Villa, Big Ocean Views| Breathtaking Sunsets
A covered outdoor area with a ceiling fan, a view of the sea, and a distant building.

2. 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, (55 reviews)
"Great location. Pretty views of Bay. Comfortable rooms. Enjoyed our brief stay for July 4th."
United States
Jorge D.
The price is CA $238
CA $696 total
includes taxes & fees
Oct 28 - Oct 29
Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA
A living room with a sofa, two armchairs, a coffee table, and a ceiling fan. There is a large window with a view of the beach and a patio area with outdoor furniture.

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

Villa 5020 on Duck Key Boat Slip Available - 2BD 2.5BA
Duck Key
9.0 out of 10, Wonderful, (16 reviews)
"Everything was perfect. Great place to stay"
United States
Kirk r.
The price is CA $265
CA $728 total
includes taxes & fees
Oct 28 - Oct 29
Villa 5020 on Duck Key Boat Slip Available - 2BD 2.5BA
An outdoor dining area with tables and chairs, overlooking a body of water.

4. Oceanfront Tiny Villa in the Heart of the FL Keys

Oceanfront Tiny Villa in the Heart of the FL Keys
Marathon
9.8 out of 10, Exceptional, (17 reviews)
"Great stay!"
United States
Nick E.
The price is CA $263
CA $682 total
includes taxes & fees
Oct 28 - Oct 29
Oceanfront Tiny Villa in the Heart of the FL Keys
A covered outdoor area with a table and chairs, overlooking a body of water with boats and a dock.

5. Villa 7079 on Duck Key - Boat Slip Available

Villa 7079 on Duck Key - Boat Slip Available
Marathon
The price is CA $371
CA $1,076 total
includes taxes & fees
Oct 28 - Oct 29
Villa 7079 on Duck Key - Boat Slip Available
Living area

6. 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, (48 reviews)
"We had a great stay!!"
United States
lissa h.
The price is CA $378
CA $945 total
includes taxes & fees
Oct 29 - Oct 30
Charming 3-bedroom house featuring a heated private pool.
A covered outdoor area with a table set for dining, overlooking a body of water and buildings.

7. Canal Front, 3 BR, Cabana Club, Sleeps 8

Canal Front, 3 BR, Cabana Club, Sleeps 8
Marathon
9.2 out of 10, Wonderful, (5 reviews)
"Place was perfect. Property manager was amazing and always answered questions within minutes. Definitely would stay again"
United States
lori p.
The price is CA $378
CA $1,296 total
includes taxes & fees
Oct 28 - Oct 29
Canal Front, 3 BR, Cabana Club, Sleeps 8
A covered outdoor dining area with a view of a turquoise pool and palm trees.

8. 4 BR with 32 Ft Boat Slip, Sleeps 10

4 BR with 32 Ft Boat Slip, Sleeps 10
Marathon
10.0 out of 10, Exceptional, (166 reviews)
"Very nice house, nicely decorated and clean. The children really enjoyed being on the canal, fishing, paddle boarding and kayaking. Plenty of room for our boat on the nice dock. We checked out the pool that was a drive down to Key Colony Beach area but did miss having our own pool at the house for our convenience. Our host was always available and helpful with any questions."
United States
Debra B.
The price is CA $536
CA $1,514 total
includes taxes & fees
Nov 2 - Nov 3
4 BR with 32 Ft Boat Slip, Sleeps 10
A modern kitchen with a large island, pendant lights, and a view to the outside.

9. 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
9.0 out of 10, Wonderful, (2 reviews)
"Very relaxing, we were in the keys for my 65th it could not have been better.Thank you again!"
United States
Anonymous traveller
The price is CA $571
CA $1,391 total
includes taxes & fees
Oct 29 - Oct 30
Villa 7205 on Duck Key - 3 BR & 3 BA - Boat Slip available
A coastal residential area with houses featuring grey roofs and surrounded by lush greenery.

10. 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
9.8 out of 10, Exceptional, (13 reviews)
"House was awesome, great shape, comfortable beds, clean. Great location, it was central to all the keys. Would definitely stay again "
United States
gabe h.
The price is CA $824
CA $1,710 total
includes taxes & fees
Oct 31 - Nov 1
4 Bedroom 3 Bathroom Sanctuary Villa W/ Private Pool & 35ft dock upon request
A pool area with lounge chairs and a view of the ocean.

11. 🌊 Private Oasis With Pool Spa Dock and Ocean right in your backyard 🌊 allow pets

🌊 Private Oasis With Pool Spa Dock and Ocean right in your backyard 🌊 allow pets
Marathon
9.2 out of 10, Wonderful, (66 reviews)
"Location is fantastic. House needs some work on the bathrooms but overall we had a wonderful time! Would book again."
United States
Becky F.
The price is CA $701
CA $1,749 total
includes taxes & fees
Nov 7 - Nov 8
🌊 Private Oasis With Pool Spa Dock and Ocean right in your backyard 🌊 allow pets
A balcony with a view of the ocean, furnished with a table and chairs, and palm trees.

12. 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, (4 reviews)
"Our stay here was very nice. Everything was clean and comfortable. The pool was enjoyable the one time we used it. Sitting on the deck gazing out to sea was exactly what I needed. Spotting a crocodile swim by was exciting!"
United States
Anonymous traveller
The price is CA $2,333
CA $4,101 total
includes taxes & fees
Nov 20 - Nov 21
Private Beach / Private overwater dock / Heated Pool / Mahi Key
A resort with a swimming pool, lounge chairs, and a view of the ocean.

13. Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort

Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort
2.5 star property
Marathon
9.2 out of 10, Wonderful, (147 reviews)
"It is an excellent place."
United States
Arianna
The price is CA $226
CA $293 total
includes taxes & fees
Oct 28 - Oct 29
Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort
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

Kingsail Resort

Kingsail Resort

10/10 Excellent
"We were pleasantly surprised by the spacious, well-equipped room, which had a stove, fridge, and microwave. The room was clean and the king sized bed was really comfortable. The front desk staff were very kind and helpful. This resort offers a great value for the money and we will be staying here again."
Kathrine 2-night trip
Posted 1 hour ago
Kingsail Resort

Find out more about Long Key

Long Key Vacation Homes information

Number of reviews
313
Accommodation
1585 Vacation Homes
Lowest Price
CA $293
Highest Price
CA $1,906

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