Holiday Homes in Long Key

Start date: Check-in selected.
To Date
End date: Check-out
    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
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
17 Oct - 19 Oct
In one month
31 Oct - 2 Nov
In two months
28 Nov - 30 Nov
In three months
26 Dec - 28 Dec

Featured Holiday Homes in Long Key

The Hammocks at Marathon
Outdoor pool, pool umbrellas, pool loungers

The Hammocks at Marathon

2.5 star property
9.0 out of 10, Wonderful, (104)
"Was a wonderful stay! The pool is very nice, and very clean room "
The Hammocks at Marathon
Perla Blanca – 4 BR, 5 BA Oasis w/ Pool, hot tub, dock, kayaks near beach.
Exterior

Perla Blanca – 4 BR, 5 BA Oasis w/ Pool, hot tub, dock, kayaks near beach.

9.8 out of 10, Exceptional, (49)
"House was spotless, very bright and open! We really enjoyed the pool and even saw a few manatees in the canal! Great location, will be returning next time we’re in the Florida Keys!"
Perla Blanca – 4 BR, 5 BA Oasis w/ Pool, hot tub, dock, kayaks near beach.
Best Deals in Duck Key . 2 Bedroom /2 Bath w/40' 'Dock, Trailer Storage Incl,
Marina

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

10.0 out of 10, Exceptional, (179)
"Beautiful property. Great location. We thoroughly enjoyed ourselves. "
Best Deals in Duck Key . 2 Bedroom /2 Bath w/40' 'Dock, Trailer Storage Incl,
Restful waterfront townhome with deck, great water views & washer/dryer
Exterior

Restful waterfront townhome with deck, great water views & washer/dryer

9.2 out of 10, Wonderful, (87)
"Great place"
Restful waterfront townhome with deck, great water views & washer/dryer
Piece of Paradise located at Hawks Cay in Duck Key
Pool

Piece of Paradise located at Hawks Cay in Duck Key

9.6 out of 10, Exceptional, (5)
Piece of Paradise located at Hawks Cay in Duck Key
Finest location in Coral Lagoon. End unit with bay views and boat slip!
Marina

Finest location in Coral Lagoon. End unit with bay views and boat slip!

9.6 out of 10, Exceptional, (184)
"Great place to stay, amazing location, great hosts!"
Finest location in Coral Lagoon. End unit with bay views and boat slip!
Tarpon Lagoon 5 Bedroom 4 Bath with heated pool on crystal clear deep Lagoon
Outdoor pool, a heated pool

Tarpon Lagoon 5 Bedroom 4 Bath with heated pool on crystal clear deep Lagoon

8.8 out of 10, Excellent, (30)
"We had a great time fishing off the dock very clean will definitely come back to this place"
Tarpon Lagoon 5 Bedroom 4 Bath with heated pool on crystal clear deep Lagoon
Sandal Escape: 6BR Canal Front Oasis w/ Heated Pool, Dog-Friendly, Dockage & Fast Atlantic Access
Terrace/patio

Sandal Escape: 6BR Canal Front Oasis w/ Heated Pool, Dog-Friendly, Dockage & Fast Atlantic Access

9.8 out of 10, Exceptional, (17)
"2 familys, plenty of room and everything we needed. Great host communications. Would definitely stay again "
Sandal Escape: 6BR Canal Front Oasis w/ Heated Pool, Dog-Friendly, Dockage & Fast Atlantic Access
TJ1 Beach, Pool, Kitchen, Sleep 6, HotTub, W&D, Dock, BBQ, WiFi, Parking, Tennis
On the beach, sun-loungers

TJ1 Beach, Pool, Kitchen, Sleep 6, HotTub, W&D, Dock, BBQ, WiFi, Parking, Tennis

9.4 out of 10, Exceptional, (26)
"My friends and i enjoyed our stay. Easy access to multiple restaurants and grocery items store. The place was clean and had everything we needed. The pool and hot tub were great."
TJ1 Beach, Pool, Kitchen, Sleep 6, HotTub, W&D, Dock, BBQ, WiFi, Parking, Tennis
Next availability from May 18th, 2024 - The Last Resort, Islamorada - MM76.7
Terrace/patio

Next availability from May 18th, 2024 - The Last Resort, Islamorada - MM76.7

10.0 out of 10, Exceptional, (85)
"Wonderful place to stay for families. We loved it. Rooms and bathrooms were fantastic. Michele was a great host that made sure our stay was perfect. "
Next availability from May 18th, 2024 - The Last Resort, Islamorada - MM76.7
KCB-access Private Cabana Club, Dock on Canal, PET Friendly, Pickle ball courts
On the beach

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

9.4 out of 10, Exceptional, (80)
"This place was clean, quiet, safe, & family friendly. The locals were kind and welcoming. I would totally recommend this property to anybody wanting to visit the Keys! Also, it is centrally located so it is real easy to do a day trip/afternoon excursion in either direction."
KCB-access Private Cabana Club, Dock on Canal, PET Friendly, Pickle ball courts
Waterfront Oasis with Boat Dock & Pool!
Fridge, microwave, oven, stovetop

Waterfront Oasis with Boat Dock & Pool!

9.4 out of 10, Exceptional, (75)
"Spacious house, great pool, terrific location, lots to do in the area for all ages. Very different from other parts of Florida that I have been to. Lovely little beach a short walk away called Sunset Beach. Everyone of all ages shows up with a drink and/or snack and gets to listen to the Marathon singers and watch a the sunset."
Waterfront Oasis with Boat Dock & Pool!
OCEAN VIEW ANGLERS REEF - POOL, DOCK, BEACH. Walk or Bike to local food + bars
Exterior

OCEAN VIEW ANGLERS REEF - POOL, DOCK, BEACH. Walk or Bike to local food + bars

10.0 out of 10, Exceptional, (196)
"We just got back from Islamorada and cannot stop talking about our trip. This property was clean and comfortable and the private development had everything we wanted. Everyone was very nice. I will definitely rent again if/when we return."
OCEAN VIEW ANGLERS REEF - POOL, DOCK, BEACH. Walk or Bike to local food + bars
🌊 Private Oasis With Pool Spa Dock and Ocean right in your backyard 🌊 allow pets
Beach towels

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

9.2 out of 10, Wonderful, (48)
"A wonderful vacation rental. The house was very clean on arrival. Kitchen was fully equipped. The dock was a dream for taking the boat out everyday. We enjoyed the pool in the afternoons. Each bedroom has an en suite bathroom which is ideal in a vacation rental. I would recommend and we will most likely try to book again next year. "
🌊 Private Oasis With Pool Spa Dock and Ocean right in your backyard 🌊 allow pets
Newly Renovated 4BR/3BA Home in Marathon with Private Pool, Jetted Tub, and 40' Canal Dockage
Dining

Newly Renovated 4BR/3BA Home in Marathon with Private Pool, Jetted Tub, and 40' Canal Dockage

Newly Renovated 4BR/3BA Home in Marathon with Private Pool, Jetted Tub, and 40' Canal Dockage
Waterfront! 4 Bed/3 BA Townhome, 32FTDock, Cabana Club, Paddleboard, Beach Gear!
Beach nearby

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

2.0 star property
10.0 out of 10, Exceptional, (157)
"We had an awesome experience. The host, Heather, was quick to respond, the hohse was well kept and clean, and the Cabana Club was a great perk. We would absolutely stay here again."
The price is NZ$1,935
includes taxes & fees
12 Oct - 13 Oct
Waterfront! 4 Bed/3 BA Townhome, 32FTDock, Cabana Club, Paddleboard, Beach Gear!
Spacious Waterfront Home on a Direct Ocean Access Canal with a Chilled Pool
Property grounds

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

9.4 out of 10, Exceptional, (73)
"My brother my son and three other friends stayed the first five days. Fish bonded had a great time everyone thought the accommodations were great. Second five days my son the rest of my family joined us eight adults for children. Accommodated all of us very well. Pool was great location was very good."
Spacious Waterfront Home on a Direct Ocean Access Canal with a Chilled Pool
MILLION DOLLAR VIEW very private 4 bedroom resort with pool, pier, kayaks, spa
Terrace/patio

MILLION DOLLAR VIEW very private 4 bedroom resort with pool, pier, kayaks, spa

10.0 out of 10, Exceptional, (26)
"We had a family with 3 generations and there was something for everyone. We had an amazing week of fun and relaxation. "
MILLION DOLLAR VIEW very private 4 bedroom resort with pool, pier, kayaks, spa
CLEAR water views @Tiki haven! Quick ocean access, Pool, HotTub, FUN! FREE ICE!
Outdoor pool, a heated pool

CLEAR water views @Tiki haven! Quick ocean access, Pool, HotTub, FUN! FREE ICE!

9.8 out of 10, Exceptional, (119)
"Everything went smoothly from checking in to checking out. Place was very clean and nicely decorated. Kitchen supplied well with dishes, utensils, pots and pans. A/C was nice a cold. The outside was like a little slice of heaven for us. We couldn’t have been any more pleased with our choice."
CLEAR water views @Tiki haven! Quick ocean access, Pool, HotTub, FUN! FREE ICE!
Manatee Bay , Pool table, Jacuzzi, Pool, Kayaks, REDUCED RATES AVAIL NOW<br>
Outdoor pool, a heated pool

Manatee Bay , Pool table, Jacuzzi, Pool, Kayaks, REDUCED RATES AVAIL NOW<br>

8.4 out of 10, Very good, (94)
"Loved our stay! All was clean and comfortable. House had all we needed and husband fished off the dock everyday and went kayaking. Quiet neighborhood- just perfect. Hope to come back again!"
Manatee Bay , Pool table, Jacuzzi, Pool, Kayaks, REDUCED RATES AVAIL NOW<br>
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Long Key Hotel Reviews

Cheeca Lodge & Spa

Cheeca Lodge & Spa

10/10 Excellent
"Yes"
Donna 1-night trip
Posted 2 days ago
Cheeca Lodge & Spa

Find out more about Long Key

Find out more about Long Key

Long Key Holiday Homes information

Number of reviews
1,440
Accommodation
1706 Holiday Homes
Lowest Price
NZ$1,935
Highest Price
NZ$1,935

Explore a world of travel with Expedia

Explore a world of travel with Expedia