Windley Key Holiday Rentals

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Check prices for these dates

Holiday Rentals in Windley Key

Breezy Palms Resort

2.5 star property
8.6 out of 10, Excellent, (410)
"We had a wonderful time. The unit had everything we needed we will definitely stay here again. "
The price is AU$383
includes taxes & fees
11 Mar - 12 Mar
Breezy Palms Resort

The Islands of Islamorada

4.0 star property
9.8 out of 10, Exceptional, (52)
"Lovely room with friendly staff. "
The price is AU$1,520
includes taxes & fees
23 Feb - 24 Feb
The Islands of Islamorada

Key Largo Cottages

2.5 star property
9.4 out of 10, Exceptional, (20)
"Love this place! Very friendly and secluded. Not your typical resort-look elsewhere if that’s what you want. But if you want a friendly private sailing camp where you hang out with other fun people and like to sail and kayak, this is absolutely it! The use of the sailboat alone more than pays for the room."
The price is AU$767
includes taxes & fees
18 Feb - 19 Feb
Key Largo Cottages

Beachfront Retreat w Pool, Boat Ramp & Dock Rental

9.0 out of 10, Wonderful, (28)
"Nice facilities. Wish we had better weather. Always enjoy our home away from home. KEYS LIFE FOR ME!!!!"
The price is AU$680
includes taxes & fees
12 Mar - 13 Mar
Beachfront Retreat w Pool, Boat Ramp & Dock Rental

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

9.8 out of 10, Exceptional, (46)
"We stayed a week in the wonderful resort at Kawama. The lagoon was right in front of our unit. There were beautiful tropical fish in the lagoon as well as tarpons and lobster! The 2 pools were heated and delightful to swim in. We love walking out to the end of the jetty each evening to watch the sunset. It was a fantastic place to spend a week and soak up the sun."
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool

New Tiny Home- Paddle Boards, Kayaks, Pool, Marina

9.4 out of 10, Exceptional, (50)
"Very nice cozy place. We loved the location so close to shopping and restaurants. We didn't have time to use any of the amenities but appreciate their availability."
The price is AU$773
includes taxes & fees
2 Mar - 3 Mar
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina

Cozy Waterfront Retreat w/ Private Boat Dock + Tiki

9.8 out of 10, Exceptional, (10)
"Really nice place, no surprises. Location was excellent and pictures and description very accurate. Unfortunately, the weather was not in our favor but can't control that! Would definitely stay here again."
The price is AU$595
includes taxes & fees
23 Feb - 24 Feb
Cozy Waterfront Retreat w/ Private Boat Dock + Tiki

Island Bay Resort

2.5 star property
9.8 out of 10, Exceptional, (100)
"Lovely oasis just outside key largo. It’s a strip of land where there’s 10 individual bungalows and ours was beautifully furnished. The grounds are well lit & the strip leads down to private access to a beach / marina which provides paddle boards / canoes & pedaloes. There’s hardly any access to beach / marina in key largo or around & all properties section off their own portion of the water. Bed very comfy & very relaxing. Hosts very friendly too. Thoroughly recommended. "
Island Bay Resort

Beautiful Escape In Paradise

8.0 out of 10, Very good, (3)
"Great location to get to everywhere we needed to in Key Largo!"
Beautiful Escape In Paradise

Waterfront Beach, Pool, Dock, Kayaks, Paddleboards

9.6 out of 10, Exceptional, (101)
"If you are looking for an easy place to stay near Pennekamp State Park, this is a great option. Our family of 5 (4 adults 16 year old) enjoyed the great views and convenient location. It's small but adequate and had everything we needed for a couple of nights! "
The price is AU$931
includes taxes & fees
18 Feb - 19 Feb
Waterfront Beach, Pool, Dock, Kayaks, Paddleboards

Ocean Front Private Beach, Pool/Hot Tub, Pool Bar, Marina with Cafe

9.8 out of 10, Exceptional, (168)
"Clean, short walk to the beach or pool. Great place to stay."
Ocean Front Private Beach, Pool/Hot Tub, Pool Bar, Marina with Cafe

Cozy place in Calusa Key Largo

9.4 out of 10, Exceptional, (6)
"We enjoyed our time there it was very nice place. A really great rv park with a pool. And close to everything in Key largo "
The price is AU$530
includes taxes & fees
24 Feb - 25 Feb
Cozy place in Calusa Key Largo

Welcome to Paradise!

9.6 out of 10, Exceptional, (57)
"We love Kawama and this unit and it's host are A. We hope to be back."
Welcome to Paradise!

Mangrove Marina and Resort Aqualodge Houseboats

3.0 star property
9.4 out of 10, Exceptional, (327)
"We stayed in the Grey Lady and it was the perfect slip! Quiet, views of the bay/mooring field/mangroves. Limited kitchen amenities if you are "eating in". All staff friendly and helpful. WiFi sketchy."
Mangrove Marina and Resort Aqualodge Houseboats

Completely Remodeled 3/3 in the heart of Key Largo (Oceanside)

10.0 out of 10, Exceptional, (183)
"House was perfect for our family. 5 adults. Walk to ocean.Great communication with host. Highly reccomend. "
Completely Remodeled 3/3 in the heart of Key Largo (Oceanside)

Oceanfront Property with Elevator, Lagoon and 2 Heated Pools

9.6 out of 10, Exceptional, (141)
"Best equipped condo ever, also nice firm mattresses. The only little glitch, was getting the keys out of the lock box. This could be replaced! We would love to stay here again!"
Oceanfront Property with Elevator, Lagoon and 2 Heated Pools

Key Largo, Calusa Resort, 2 bedroom 1 bath with screened in patio

9.4 out of 10, Exceptional, (69)
"The trailer is very nice and well equipped. There are a lot of trailers in a relatively small area. It feels crowded though in stuff not people. There are some nice amenities a pool laundry etc. I don't have a boat but it seems like it would be good for that. Most activities will require auto travel."
Key Largo, Calusa Resort, 2 bedroom 1 bath with screened in patio

WOW! WATERFRONT CANAL HOME-RELAXING, FRESH & CLEAN-FISH, SWIM, SNORKEL CLOSE BY!

9.6 out of 10, Exceptional, (76)
"Great and clean place to stay. Chris was the perfect host. "
WOW! WATERFRONT CANAL HOME-RELAXING, FRESH & CLEAN-FISH, SWIM, SNORKEL CLOSE BY!

Relax in your one bedroom Oceanfront Suite in Tavernier FL. Florida Keys.

9.8 out of 10, Exceptional, (38)
"Loved the property, location and amenities! The condo was exactly as advertised. "
Relax in your one bedroom Oceanfront Suite in Tavernier FL. Florida Keys.

VOTED BEST KEY LARGO VACATION RENTAL

10.0 out of 10, Exceptional, (73)
"We had a great time. The accommodations had everything we needed. We loved having access to kayaks and paddle boards. Great and safe area to walk and ride bikes. They had fire pits and a great rock peninsula area to view sunsets and sunrises. There was a marina with fishing opportunities leaving area marina. The only negatives were no working bikes and not a fourth bedroom. It really was 3 bedrooms with a den area with a couch that made a bed.Would go again! Norman, the property manager, was the...
VOTED BEST KEY LARGO VACATION RENTAL
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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Other types of properties in Windley Key you may be interested in

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

3.5 star property
8.0 out of 10, Very good, (1009)
"Was great for a resort. Onsite restaurants have great food and amazing views. Contstant piped in music (all throughout the resort— on the beaches, the pools, the walkways, etc) was a downside but they might be par for the course on a resort. Biggest downside was that there is no hot tub on the premises. This might change as some of the resort is still under construction. Biggest upside is the amazing views and the wonderful staff. Everyone was not only polite, but helpful, and friendly. "
The price is AU$976
includes taxes & fees
23 Feb - 24 Feb
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Coconut Cove Resort and Marina

2.5 star property
7.4 out of 10, Good, (719)
"Very friendly Staff. Enjoyed our stay"
The price is AU$540
includes taxes & fees
24 Feb - 25 Feb
Coconut Cove Resort and Marina

Fisher Inn Resort & Marina

3.5 star property
7.8 out of 10, Good, (1003)
"The staff is so friendly, and the free paddle boards and bikes were a huge bonus. We will stay here again!"
The price is AU$496
includes taxes & fees
2 Mar - 3 Mar
Fisher Inn Resort & Marina
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.