Holiday Homes in Windley Key

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Featured Holiday Homes in Windley Key

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

9.4 out of 10, Exceptional, (50)
"Loved the Tiny Home! Perfect for our family of five, 3 of which are teenagers. Great community, amenities, and friendly folks. Key Largo is such a fun place to vacation! Host was very communicative and friendly, would stay here again! Thanks for a fun trip!"
The price is AU$784
includes taxes & fees
2 Mar - 3 Mar
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina

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

10.0 out of 10, Exceptional, (183)
"We enjoyed our stay can't think of any issues Defiantly would go back "
Completely Remodeled 3/3 in the heart of Key Largo (Oceanside)

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

Oceanfront Estate with Private 350 foot Pier, Heated Pool, Pet Friendly

9.4 out of 10, Exceptional, (89)
"We were fortunate to get just one day of rain, and otherwise had wonderful weather, which was great because the outdoor space at this property is wonderful. There is a large area to play soccer or throw a ball, as well as beach, long and low dock, and kayaks to use. The outside space is truly what makes this house special. The location is very good and easy to get to -- you're just a handful of miles from some of the more touristy things in Islamorada, making this a quiet spot that still has...
Oceanfront Estate with Private 350 foot Pier, Heated Pool, Pet Friendly

Mariners Club Townhouse, Unit 603, Epic Amenities, Tennis & Indoor Pickleball

2.5 star property
10.0 out of 10, Exceptional, (3)
"It is a lovely property! Ee had a peaceful, relaxing stay!"
Mariners Club Townhouse, Unit 603, Epic Amenities, Tennis & Indoor Pickleball

Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball

9.6 out of 10, Exceptional, (10)
"Our group was looking for a warm spot to relax and this place delivered! We had quite a few of us, so it was great to have many places to sleep and lots of living space. Mariner's Club was a beautiful spot and the pools were a beautiful place to spend relaxing days. We had no problem finding great restaurants nearby using Erick's recommendations. "
Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball

Islamorada Home with Private Beach Freshly updated Waterfront and Swimming Pool

8.8 out of 10, Excellent, (10)
"Great location with access to Gulf and Atlantic (a short ride away). Super clean and exactly as advertised. No disappointments. Hosts very responsive to inquiries."
Islamorada Home with Private Beach Freshly updated Waterfront and Swimming Pool

Islamorada Boaters Paradise with 70' Dock and private beach access..

10.0 out of 10, Exceptional, (19)
"Everything was amazing for our stay. We were able to have the boat right at the house for easy access for sunset boat rides and our everyday fishing adventures. "
Islamorada Boaters Paradise with 70' Dock and private beach access..

PRIVATE WATERFRONT HOUSE DOCK 4KAYAKS 2SUP BOARD GOLF CART

10.0 out of 10, Exceptional, (137)
"The home was in a great area, all amenities needed were included. Owner was very communicative and everything was very efficient. Golf cart, boat, jetskis etc were a fun touch."
The price is AU$1,417
includes taxes & fees
7 Mar - 8 Mar
PRIVATE WATERFRONT HOUSE DOCK 4KAYAKS 2SUP BOARD GOLF CART

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$1,031
includes taxes & fees
25 Feb - 26 Feb
Waterfront Beach, Pool, Dock, Kayaks, Paddleboards

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

9.6 out of 10, Exceptional, (16)
"This cluster of cottages is a small “community” within a neighborhood off Highway 1 in the Keys. Very close to things you need like restaurants, grocery and close enough to beachy areas like Sombrero Beach on Marathon or Bahia Honda a bit farther south. Loved the quiet pool and our fire pit for those cooler January nights. The neighbors seemed to be a mix of permanent residents, boaters, renters and snowbirds. This is ideal for couples and maybe kids who don’t mind sharing a small double (full)...
Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada

Charming Canal-Front House | WiFi+Swim+Kayak+Fish

10.0 out of 10, Exceptional, (2)
"All was great we had what we needed and more it was very clean and our host communicated well. We had lots of fun and this house facilitated that!"
Charming Canal-Front House | WiFi+Swim+Kayak+Fish

4BR/4BA Mariner's Club Townhouse 607 with Oasis Pool, Marina, Game Room & More

10.0 out of 10, Exceptional, (4)
"Property was beautiful and perfectly fit our needs for our business fishing trip! "
4BR/4BA Mariner's Club Townhouse 607 with Oasis Pool, Marina, Game Room & More

Bungalow #5 - 2 Bed/1 Bath & Pool in Islamorada

9.6 out of 10, Exceptional, (10)
"We stayed at this home during the time between Christmas and New Years (me, my husband and our two teenage children). The house is nice but, be aware it is small. We had a day with rain and with everyone being in the house it just felt cramped. When we arrived the toilet was running constantly. We had to take the top off of the toilet and fix it every time we used the restroom until a repairman came the following afternoon to fix it. If you are traveling to the area during this time of...
Bungalow #5 - 2 Bed/1 Bath & Pool in Islamorada

Key Largo Villa, Kawama J3, 3/3, Ocean,Marina,Lagoon,Pools,Kayaks&bikes

9.6 out of 10, Exceptional, (127)
"Clean, great location, plenty of room,"
Key Largo Villa, Kawama J3, 3/3, Ocean,Marina,Lagoon,Pools,Kayaks&bikes

Overlooking the Lagoon and Pool Includes Use of Golf Cart & 2 Kayaks

10.0 out of 10, Exceptional, (21)
"The host was very easy to work with and responded quickly. We were supposed to fly into Miami the morning Hurricane Milton made land fall so our trip was cancelled. Based on the weather circumstances the owner worked with us and refunded our payment. We are in the process of re-planning our trip and will stay here in the future! "
Overlooking the Lagoon and Pool Includes Use of Golf Cart & 2 Kayaks

907 Mariners Club | 3 Bed, 3 Bath

10.0 out of 10, Exceptional, (5)
"This was a great spot to escape the winter weather in the north. The property was excellent and just as described. Would have liked a direct check-in rather than having to stop at the office, but it was in the way. Also some basic starter supplies would have been nice like some coffee pods, sweetener and some basic spices. The amenities such as the gym and pool were great. Definitely would stay here again. Highly recommend. "
907 Mariners Club | 3 Bed, 3 Bath

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

Charming 2-bedroom water-front home in Islamorada in the Florida Keys

Charming 2-bedroom water-front home in Islamorada in the Florida Keys

NEW! GOLF CART! VOTED #1 OCEANSIDE CASA AZUL! PICKLEBA-KAYAKS- BEACH- POOLS-FISH

9.8 out of 10, Exceptional, (185)
"Check in/ out was easy. Host is very responsive. Very clean and well stocked. There was a wedding the weekend we were there so they took over the tiki hut area and played loud music the Friday and Sunday nights, so that was unfortunate. Lagoon was awesome, we bbq’d by the ocean every night (which we loved) so be sure to get charcoal as there is no gas bbq onsite. Aside from the loud wedding no complaints! I wouldn’t hesitate to book it again. "
The price is AU$1,777
includes taxes & fees
12 Mar - 13 Mar
NEW! GOLF CART! VOTED #1 OCEANSIDE CASA AZUL! PICKLEBA-KAYAKS- BEACH- POOLS-FISH
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 property types in Windley Key

Breezy Palms Resort

2.5 star property
8.6 out of 10, Excellent, (411)
"We had a wonderful time. The unit had everything we needed we will definitely stay here again. "
The price is AU$400
includes taxes & fees
13 Mar - 14 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$1,477
includes taxes & fees
27 Feb - 28 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
20 Feb - 21 Feb
Key Largo Cottages
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.