Long Key vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Long Key

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Guest favorite

Townhouse in Duck Key

4.98 out of 5 average rating, 140 reviews

3Bd 3Ba Cottage/Village at Hawks Cay/Ocean Views

Our Cottage is located between Islamorada and Marathon Key on Duck Key at the Village of Hawks Cay; one of the most desirable locations in the Florida Keys. This is at Mile Marker 61. With ocean views, high end finishes, comfy beds and plenty to do in the surrounding areas, the Cottage offers something for everyone. The outdoor green space overlooking the water is gorgeous. Sunsets are amazing right off the screened in lanai. We hope to host you as our guest in the beautiful Florida Keys.

Nov 30 – Dec 7

R9,029 ZAR per night
Guest favorite

Guest suite in Marathon

4.98 out of 5 average rating, 140 reviews

Casa Mariposa: Sombrero Beach Neighborhood

Book your getaway now at Casa Mariposa in the heart of the Florida Keys! See why we were rated a top 15 cozy retreat in the Keys, selected as 1 0f 24 amazing AirBNB rentals in the Keys, and 1 of 23 Amazing Airbnbs in The Keys. Step out the door from your private suite to a coral path that leads to our 50' heated/cooled lap pool, waterfall and large patio. Avoid beach parking fees with a short walk from your suite at Casa Mariposa! Contact us if you are interested in an other lengths of stay.

May 3 – 10

R3,681 ZAR per night
Guest favorite

Cottage in Islamorada

4.85 out of 5 average rating, 124 reviews

1 BD PRIVATE HOUSEBOAT/ COTTAGE TARPON

Tucked away in the vibrant Florida Keys, is our pristine paradise. We are located in the heart of Islamorada, where the weather is always gorgeous, the fishing never disappoints, and the sunsets are mesmerizing. If you are seeking a relaxing get away, look no further. On site, you will have the luxury of renting your own private boat. Boat rentals are 20% off for guests! Unfortunately, we do not have spare slips for private boats at this time. A 5% lodging tax will be charged on arrival.

Nov 16 – 23

R3,703 ZAR per night

Popular amenities for Long Key vacation rentals

Other great vacation rentals in Long Key

Guest favorite

Home in Marathon

4.97 out of 5 average rating, 31 reviews

Beach House, Private Pool & Dock, Gulf Sunset view

Nov 9 – 16

R10,598 ZAR per night
Guest favorite

Condo in Marathon

4.93 out of 5 average rating, 14 reviews

Paradise @ MM61 - Waterfront 1 BR / 1 Bath Condo

Dec 14 – 21

R3,617 ZAR per night
Guest favorite

Bungalow in Islamorada

4.96 out of 5 average rating, 28 reviews

Dream in Paradise! King Master, Queen Guest, Pool

Aug 22 – 29

R12,565 ZAR per night
Guest favorite

Cottage in Islamorada

4.97 out of 5 average rating, 63 reviews

Islamorada 2BR, 1BA w/ heated pool and firepit

Aug 5 – 12

R7,347 ZAR per night
Guest favorite

Home in Marathon

5.0 out of 5 average rating, 8 reviews

Million Dollar View

Oct 12 – 19

R14,768 ZAR per night
Guest favorite

Home in Key Largo

5.0 out of 5 average rating, 43 reviews

The Paradise 2

Feb 2 – 9

R6,573 ZAR per night
Guest favorite

Cottage in Islamorada

4.94 out of 5 average rating, 36 reviews

Islamorada bungalow 2 bed & pool

Sep 18 – 25

R8,161 ZAR per night
Guest favorite

Cabin in Marathon

4.89 out of 5 average rating, 56 reviews

Conch Key Cottages with Sailboat

Mar 7 – 14

R7,023 ZAR per night
Superhost

Home in Marathon

5.0 out of 5 average rating, 11 reviews

Oceanfront w/ Dock, Hot Tub & Secluded

Aug 16 – 23

R5,346 ZAR per night
Guest favorite

Home in Marathon

4.97 out of 5 average rating, 31 reviews

The Gulf Cottage at Marathon Key

Jun 7 – 14

R2,839 ZAR per night
Guest favorite

Home in Islamorada

4.96 out of 5 average rating, 55 reviews

Tropical Getaway 3/3 with 100’ boat dock and pool

Sep 17 – 24

R9,839 ZAR per night
Guest favorite

Home in Duck Key

5.0 out of 5 average rating, 29 reviews

Private Pool Tropical Oasis - Centrally Located

Nov 6 – 13

R11,357 ZAR per night

Other great vacation rentals in Long Key

Guest favorite

Home in Marathon

5.0 out of 5 average rating, 19 reviews

Paradise in the Keys

Jan 17 – 24

R16,455 ZAR per night
Guest favorite

Home in Marathon

4.93 out of 5 average rating, 28 reviews

Waterfront Villa & Sunset Views

Jun 18 – 25

R5,574 ZAR per night
Superhost

Tiny home in Big Pine Key

4.8 out of 5 average rating, 88 reviews

Breezy pines 28 foot 5th wheel trailer .

Nov 20 – 27

R2,235 ZAR per night
Guest favorite

Home in Marathon

5.0 out of 5 average rating, 29 reviews

100' Dockage, Pool, Kayaks, Paddle Board, Bikes!

Oct 23 – 30

R9,495 ZAR per night
Guest favorite

Tiny home in Key Largo

4.98 out of 5 average rating, 57 reviews

Oceanfront Lookout Point w/two Kayaks & Deck

Mar 4 – 11

R5,177 ZAR per night
Superhost

Villa in Marathon

4.8 out of 5 average rating, 87 reviews

Sunset Villa in Duck Key

Jan 27 – Feb 3

R9,282 ZAR per night
Guest favorite

Townhouse in Duck Key

4.96 out of 5 average rating, 57 reviews

Waterfront Retreat

Aug 6 – 13

R6,607 ZAR per night
Superhost

Villa in Marathon

4.85 out of 5 average rating, 79 reviews

Marina front villa *Family Friendly*

Jul 28 – Aug 4

R6,898 ZAR per night
Superhost

Home in Marathon

4.91 out of 5 average rating, 23 reviews

Serenity Bay Estate-FL Keys Best Kept Secret! Beau

Dec 8 – 15

R17,082 ZAR per night
Superhost

Home in Marathon

4.93 out of 5 average rating, 56 reviews

Oceanfront mermaid house pool and dock

Apr 20 – 27

R10,881 ZAR per night
Guest favorite

Home in Islamorada

4.93 out of 5 average rating, 14 reviews

3 Lux Ensuites Walk/Boat Island!

Jan 18 – 25

R10,805 ZAR per night
Guest favorite

Home in Key Largo

4.99 out of 5 average rating, 69 reviews

Little Cottage on an island

Jun 17 – 24

R3,272 ZAR per night

Destinations to explore

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  4. Monroe County
  5. Long Key