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Aug 29 - Aug 31
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Browse Select Florida Keys Vacation Homes

Our top choices for Florida Keys vacation homes

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

The Hammocks at Marathon

2.5 star property
9.0 out of 10, Wonderful, (98)
"Very nice and clean nice pool area nice tity bar an restant easy to get in and out good gym area"
The Hammocks at Marathon
Perla Blanca 4 Bed 5 Bath kayaks pool boat dock
Exterior

Perla Blanca 4 Bed 5 Bath kayaks pool boat dock

9.8 out of 10, Exceptional, (48)
"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 Bed 5 Bath kayaks pool boat dock
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, (90)
"We loved staying her so much! I had everything we needed and some. Loved the location also! Was so great!"
Manatee Bay , Pool table, Jacuzzi, Pool, Kayaks, REDUCED RATES AVAIL NOW<br>
Vacation with attitude!
Fridge, microwave, oven, stovetop

Vacation with attitude!

10.0 out of 10, Exceptional, (7)
"Good location, family friendly, very nice pool and outdoors. "
Vacation with attitude!
Piece of Paradise located at Hawks Cay in Duck Key
Pool

Piece of Paradise located at Hawks Cay in Duck Key

9.4 out of 10, Exceptional, (3)
"Amazing place. "
Piece of Paradise located at Hawks Cay in Duck Key
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool
Exterior

Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool

9.8 out of 10, Exceptional, (67)
"Such a great, gated location with access to a variety of amenities. "
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool
Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball
Outdoor pool, a heated pool

Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball

9.6 out of 10, Exceptional, (19)
"Clean , beautiful location and pools . "
Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
Beach nearby

Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

8.8 out of 10, Excellent, (86)
"Property was adequate but could use a few updates. The location was great. Easy to get to Key West near good local restaurants and beaches. Would stay again. "
The price is CA $407
CA $957 total
includes taxes & fees
Aug 24 - Aug 25
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
Snappers - King Room w/ Ocean View Wifi
Terrace/patio

Snappers - King Room w/ Ocean View Wifi

The price is CA $100
CA $140 total
includes taxes & fees
Aug 24 - Aug 25
Snappers - King Room w/ Ocean View Wifi
Old Florida Style, wrap around porch, boat basin for dockage, open water
Property grounds

Old Florida Style, wrap around porch, boat basin for dockage, open water

9.6 out of 10, Exceptional, (78)
"Took the team down to the keys for a little R&R"
Old Florida Style, wrap around porch, boat basin for dockage, open water
Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada
Outdoor pool, a heated pool

Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada

9.6 out of 10, Exceptional, (30)
"Nice property . Well kept. Good management "
Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada
🌊 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, (45)
"Great sunsets; quiet street; fantastic marine life. Frank was very responsive. The property is not brand new but delivered on what we needed: pool, great dock for fishing and keeping boat during day. Booked again for next year. "
🌊 Private Oasis With Pool Spa Dock and Ocean right in your backyard 🌊 allow pets
Don't Miss This! Deep Water Canal, Swimspa Pool, Kayaks, Walk to Tiki Bars!!
Terrace/patio

Don't Miss This! Deep Water Canal, Swimspa Pool, Kayaks, Walk to Tiki Bars!!

10.0 out of 10, Exceptional, (78)
"We had a wonderful time during our stay in the Florida Keys! The home and adjacent canal lot were spacious, comfortable, and very inviting. We completely recommend staying at Kathy's property!"
Don't Miss This! Deep Water Canal, Swimspa Pool, Kayaks, Walk to Tiki Bars!!
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

9.0 out of 10, Wonderful, (27)
"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
Sea La Vie – Key Largo Retreat in Mariner’s Club - Labor Day & Fall Specials
Pool

Sea La Vie – Key Largo Retreat in Mariner’s Club - Labor Day & Fall Specials

10.0 out of 10, Exceptional, (138)
"You would be very hard presses to find a better Key Largo location. Especially for family, boating and fishing!"
Sea La Vie – Key Largo Retreat in Mariner’s Club - Labor Day & Fall Specials
Waterfront 2BR w/ Dock, Hot Tub & Easy Ocean Access – Boaters Welcome!
Terrace/patio

Waterfront 2BR w/ Dock, Hot Tub & Easy Ocean Access – Boaters Welcome!

10.0 out of 10, Exceptional, (4)
"We had an amazing stay at this home in Marathon! The property was clean, comfortable, and perfectly set up for a week on the water. Having our boat right at the dock made it so easy to head out fishing or explore the Keys each day. The location was quiet yet close to everything we needed. Highly recommend for anyone looking for a great boating getaway!"
Waterfront 2BR w/ Dock, Hot Tub & Easy Ocean Access – Boaters Welcome!
Venetian Tropics weekly Pvt home w/heated Pool, 3 bedroom /70ft dock w/canal
Outdoor pool, a heated pool

Venetian Tropics weekly Pvt home w/heated Pool, 3 bedroom /70ft dock w/canal

9.6 out of 10, Exceptional, (58)
"The property is central location in Islamorada, best location....The outdoor area is perfect,pool heated very enjoyable.. great neighborhood..Friendly Host JoAnn is amazing, and prompt response, a delightful person, and a wonderful host!"
Venetian Tropics weekly Pvt home w/heated Pool, 3 bedroom /70ft dock w/canal
Tropical: 4BR Luxury Home Gulf Views Pool and Dock
Outdoor spa tub

Tropical: 4BR Luxury Home Gulf Views Pool and Dock

9.6 out of 10, Exceptional, (42)
"We had a great stay. Plenty of space for large family. "
Tropical: 4BR Luxury Home Gulf Views Pool and Dock
Bumpa's Big House - Bring the Grandkids!
A heated pool

Bumpa's Big House - Bring the Grandkids!

10.0 out of 10, Exceptional, (26)
"House was perfect! Pool, hot tub, putting green, 3 full size fridges, HUGE laundry room!! SO much more!"
Bumpa's Big House - Bring the Grandkids!
Direct Ocean View! 5 Bed/3 Bath with room for everyone. Large pool and Dock!
Smart TV

Direct Ocean View! 5 Bed/3 Bath with room for everyone. Large pool and Dock!

9.8 out of 10, Exceptional, (73)
"We loved the spacious home with pool and little fishing dock. The kayaks were fun too. It was roughly 30 minutes to key west and the same to marathon key. Would definitely stay again."
Direct Ocean View! 5 Bed/3 Bath with room for everyone. Large pool and Dock!
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 Florida Keys Hotel Reviews

Cheeca Lodge & Spa

Cheeca Lodge & Spa

10/10 Excellent
"Perfect experience from beginning to end. Greeted by friendly people at the gate that gave me excellent information on checking in and parking. The check in staff were very friendly and when asked if any upgrades to my room were avaliable she found me something nicer then I was able to. The room was beautiful and spacious overlooking the golf course. Parking for the room was close and convenient. And everyone in the cleaning staff were friendly and full of smiles. Only issue I had was none of the ice machines worked, I checked multiple buildings but im sure they are getting that figured out soon. Will definitely stay agian next time in Islamorada"
Nicholas 1-night trip
Posted 20 hours ago
Cheeca Lodge & Spa