Windley Key Vacation Rentals

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Check prices for these dates

Next weekend
Aug 8 - Aug 10
In two weeks
Aug 15 - Aug 17
In one month
Aug 29 - Aug 31
In two months
Sep 26 - Sep 28

Browse Select Windley Key Vacation Homes

Beachside Retreat w/ Pool, Boat Ramp Dock for Rent
Beach nearby, sun loungers, beach towels

Beachside Retreat w/ Pool, Boat Ramp Dock for Rent

9.6 out of 10, Exceptional, (33)
"Beautiful place. Our stay was quiet and wonderful. Very clean and comfortable. "
The price is CA $122
CA $408 total
includes taxes & fees
Aug 12 - Aug 13
Beachside Retreat w/ Pool, Boat Ramp Dock for Rent
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, (18)
"Clean , beautiful location and pools . "
Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball
Oceanfront 165ft beach-Dock-Heated pool-4K sq.ft 4 bed/5 bath-Next avail 8.9.25
Terrace/patio

Oceanfront 165ft beach-Dock-Heated pool-4K sq.ft 4 bed/5 bath-Next avail 8.9.25

10.0 out of 10, Exceptional, (84)
"Everything just great except need better vaccum"
Oceanfront 165ft beach-Dock-Heated pool-4K sq.ft 4 bed/5 bath-Next avail 8.9.25
OCEANFRONT ANGLERS REEF in ISLAMORADA -Pool, Dock, Beach, Kayaks, Paddle Boards
A heated pool

OCEANFRONT ANGLERS REEF in ISLAMORADA -Pool, Dock, Beach, Kayaks, Paddle Boards

10.0 out of 10, Exceptional, (183)
"We had such a nice time at the Windley Cottage. The owners effectively communicated information about the home and check in before the stay, making arrival very easy. The home was very clean and had everything that we needed. The Anglers Reef area was nice and quiet. We enjoyed walks to the docks, kayaking, and swimming in the pool. We absolutely loved Islamorada and hope to visit again!"
OCEANFRONT ANGLERS REEF in ISLAMORADA -Pool, Dock, Beach, Kayaks, Paddle Boards
Florida Keys Townhouse For Rent 2/2
Property grounds

Florida Keys Townhouse For Rent 2/2

9.4 out of 10, Exceptional, (169)
"We used this as accommodation to explore the keys for 6days and it did not disappoint. Very accurate description of the house. Nice, clean and tidy. Thank you"
Florida Keys Townhouse For Rent 2/2
Waterfront Beach, Pool, Dock, Kayaks, Paddleboards
Outdoor dining

Waterfront Beach, Pool, Dock, Kayaks, Paddleboards

9.6 out of 10, Exceptional, (116)
"Best sunrise site."
The price is CA $219
CA $572 total
includes taxes & fees
Aug 25 - Aug 26
Waterfront Beach, Pool, Dock, Kayaks, Paddleboards
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, (193)
"Great location. Beautiful, comfortable accommodations. Would absolutely return. "
OCEAN VIEW ANGLERS REEF - POOL, DOCK, BEACH. Walk or Bike to local food + bars
Waterfront Tiny House w Pool, Beach, and Boat Dock
Marina

Waterfront Tiny House w Pool, Beach, and Boat Dock

9.6 out of 10, Exceptional, (57)
"We stayed here in April 2025 - perfect location with a great patio overlooking the waterfront harbor, perfect for us. Everything you need is a short drive - grocery Publix is close enough to walk to. The tiny house is adorable and clean, well stocked kitchen - We found great place to hike /Hamock State Park and Rowell’s was a great place to swim "
The price is CA $182
CA $531 total
includes taxes & fees
Aug 21 - Aug 22
Waterfront Tiny House w Pool, Beach, and Boat Dock
Charming Home in Key Largo
Fridge, microwave, oven, stovetop

Charming Home in Key Largo

9.8 out of 10, Exceptional, (22)
"Amazing spot in the Keys. Stayed there the weekend for a wedding in Tavernier and was close to everything we needed. Would definitely stay here again when I come back. "
The price is CA $112
CA $450 total
includes taxes & fees
Aug 4 - Aug 5
Charming Home in Key Largo
7 Bedroom with Dockage, Pool, Firepit, Paddle Boards & Kayaks
Outdoor pool, a heated pool

7 Bedroom with Dockage, Pool, Firepit, Paddle Boards & Kayaks

10.0 out of 10, Exceptional, (55)
"We have stayed in one of this Hosts properties for 5 years in a row. Always clean, always great communication and we always have a great time. We highly recommend."
7 Bedroom with Dockage, Pool, Firepit, Paddle Boards & Kayaks
Tranquility Cove Beautiful Remodeled home in the heart of Islamorada.
Fridge, microwave, oven, stovetop

Tranquility Cove Beautiful Remodeled home in the heart of Islamorada.

7.4 out of 10, Good, (3)
"Three generations stayed very comfortably in this great house. It was located great for food and activities!"
Tranquility Cove Beautiful Remodeled home in the heart of Islamorada.
New Mariners Club Listing, Preferred Partner, Great Location, Epic Amenities
Outdoor pool, a heated pool

New Mariners Club Listing, Preferred Partner, Great Location, Epic Amenities

2.5 star property
10.0 out of 10, Exceptional, (18)
"This condo and the club is awesome. The pool is wonderful. We loved everything about or stay would come back! "
New Mariners Club Listing, Preferred Partner, Great Location, Epic Amenities
Single Family Home In Angler's Reef Gated Community, Beaches,Marina,Heated Pool
A heated pool

Single Family Home In Angler's Reef Gated Community, Beaches,Marina,Heated Pool

9.8 out of 10, Exceptional, (92)
"This is the best location we have stayed at in Islamorada. The community was safe and quiet, plenty to do right on site with swimming, private beach, kayaks and paddleboards, fishing off dock. We saw manatees most days in the marina. The house is exactly as listed, the owners were quick to respond and fix any issues we had. Would definitely rent again! "
Single Family Home In Angler's Reef Gated Community, Beaches,Marina,Heated Pool
Resort-Style Living at Mariner's Club – Steps from Pools, Marina, & Ocean Views!
Outdoor pool, a heated pool

Resort-Style Living at Mariner's Club – Steps from Pools, Marina, & Ocean Views!

10.0 out of 10, Exceptional, (7)
"We stayed at this property for our spring break trip and thoroughly enjoyed our stay. The home was clean, comfortable, and well-equipped with everything we needed. The location was great—close to local attractions yet peaceful enough for a relaxing getaway. The host was responsive and accommodating, making the entire experience seamless. We would definitely stay here again!"
Resort-Style Living at Mariner's Club – Steps from Pools, Marina, & Ocean Views!
611 Mariners Club Key Largo | 4 Bed, 4 Bath
A heated pool

611 Mariners Club Key Largo | 4 Bed, 4 Bath

9.0 out of 10, Wonderful, (95)
"The unit was set up perfect for my family as well as my brother-in-law‘s for a family wedding in Key Largo. The pools were beautiful. The property was well maintained and we had a wonderful time. "
611 Mariners Club Key Largo | 4 Bed, 4 Bath
NEW! Stunning 2-acre Oceanfront Estate with Private Pool ~ Beach. Very private
Smart TV, books, stereo, printers

NEW! Stunning 2-acre Oceanfront Estate with Private Pool ~ Beach. Very private

NEW! Stunning 2-acre Oceanfront Estate with Private Pool ~ Beach. Very private
Waterfront, saltwater lagoon, 2 pools, ocean access, marina, tennis, pickleball
Property grounds

Waterfront, saltwater lagoon, 2 pools, ocean access, marina, tennis, pickleball

9.8 out of 10, Exceptional, (102)
"beautiful and quite neighborhood. "
Waterfront, saltwater lagoon, 2 pools, ocean access, marina, tennis, pickleball
Keys Relaxing Getaway
Property grounds

Keys Relaxing Getaway

10.0 out of 10, Exceptional, (56)
"Beautiful,clean, great location"
Keys Relaxing Getaway
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, (65)
"Such a great little property in a awesome community! A from the host he was such a nice person and communicating was superior would definitely rent again! "
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina
Marina

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

9.4 out of 10, Exceptional, (70)
"Great tiny house, enjoyed our stay"
The price is CA $166
CA $507 total
includes taxes & fees
Aug 25 - Aug 26
New Tiny Home- Paddle Boards, Kayaks, Pool, 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.
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Top Windley Key Hotel Reviews

Reefhouse Resort & Marina

Reefhouse Resort & Marina

10/10 Excellent
"Friendly, fast service in the lobby, restaurants and bars. The property is upbeat, fun, clean. "
Kristie 1-night trip
Posted 16 hours ago
Reefhouse Resort & Marina