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Vacation Homes in Windley Key

Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball

9.6 out of 10, Exceptional, (16)
"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

10.0 out of 10, Exceptional, (82)
"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

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

2.5 star property
10.0 out of 10, Exceptional, (13)
"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

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

9.8 out of 10, Exceptional, (60)
"It was a very nice stay! Enjoyed the colorful fish in the lagoon, and the big lobster! It was a short walk to the jetty and beach."
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool

NEW OCEANVIEW CASA MAR VOTED #1! INDOOR PICKLEBALL ~ POOLS~ TENNIS~ FISH~ MARINA

10.0 out of 10, Exceptional, (98)
"Loved the location, the decor and the pool area!"
The price is ¥114,388
¥210,680 total
includes taxes & fees
Jul 2 - Jul 3
NEW OCEANVIEW CASA MAR VOTED #1! INDOOR PICKLEBALL ~ POOLS~ TENNIS~ FISH~ MARINA

Fun For All! Key Largo 3/3 Townhome Oceanside Resort

9.6 out of 10, Exceptional, (59)
"Great location and property."
Fun For All! Key Largo 3/3 Townhome Oceanside Resort

801 Mariners Club Key Largo | 4 Bed, 4 Bath

9.4 out of 10, Exceptional, (70)
"We had too much fun great central location. Good amenities!! "
801 Mariners Club Key Largo | 4 Bed, 4 Bath

Waterfront Tiny House w Pool, Beach, and Boat Dock

9.6 out of 10, Exceptional, (55)
"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 ¥24,512
¥63,202 total
includes taxes & fees
Jun 30 - Jul 1
Waterfront Tiny House w Pool, Beach, and Boat Dock

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

9.4 out of 10, Exceptional, (94)
"Great location and property! Very helpful property manager"
Oceanfront Estate with Private 350 foot Pier, Heated Pool, Pet Friendly

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

9.6 out of 10, Exceptional, (80)
"Great stay, lovely setting and location! Our second time here!"
WOW! WATERFRONT CANAL HOME-RELAXING, FRESH & CLEAN-FISH, SWIM, SNORKEL CLOSE BY!

Key Largo Relaxing Getaway

9.8 out of 10, Exceptional, (90)
"Great spot for a Key Largo get away!"
Key Largo Relaxing Getaway

Waterfront Beach, Pool, Dock, Kayaks, Paddleboards

9.6 out of 10, Exceptional, (112)
"Best sunrise site."
The price is ¥28,400
¥67,723 total
includes taxes & fees
Jul 8 - Jul 9
Waterfront Beach, Pool, Dock, Kayaks, Paddleboards

Beautiful Oceanside Mariner's 3 Bedroom Townhome

10.0 out of 10, Exceptional, (78)
"Amazing and cozy home and great location very close to the pools. "
The price is ¥60,335
¥115,433 total
includes taxes & fees
Jun 23 - Jun 24
Beautiful Oceanside Mariner's 3 Bedroom Townhome

VOTED BEST KEY LARGO VACATION RENTAL

10.0 out of 10, Exceptional, (77)
"Absolutely wish we had more time there. Wonderful place to stay!"
VOTED BEST KEY LARGO VACATION RENTAL

Beach townhouse with shared pool, tennis & marina - AC, WiFi & snowbird-friendly

8.6 out of 10, Excellent, (4)
"Fantastic spot! Thank you!"
Beach townhouse with shared pool, tennis & marina - AC, WiFi & snowbird-friendly

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

10.0 out of 10, Exceptional, (182)
"Rodger and Linda is home and Islamorada is wonderful. They are unbelievably accommodating property owners and made the trip extra special. I look forward to returning and staying there again."
OCEANFRONT ANGLERS REEF in ISLAMORADA -Pool, Dock, Beach, Kayaks, Paddle Boards

NEW! OCEANSIDE CASA PALMA!VOTED #1! GOLF CART-PICKELBAL -KAYAK- BEACH- POOL-FISH

9.8 out of 10, Exceptional, (166)
"If you want a place for the family, this is it"
NEW! OCEANSIDE CASA PALMA!VOTED #1! GOLF CART-PICKELBAL -KAYAK- BEACH- POOL-FISH

Sanctuary In Paradise Featured On H G T V

9.8 out of 10, Exceptional, (68)
"We had a great time at the house. Being right on the water and with family was a great overall vacation. The property was just as expected and we would all definitely stay there again!!!"
Sanctuary In Paradise Featured On H G T V

Beautiful updated Kawama Townhouse. Two units available. Second unit #1306961.

9.6 out of 10, Exceptional, (222)
"This was our second stay here. We love the lagoon and the location. Great experience"
Beautiful updated Kawama Townhouse. Two units available. Second unit #1306961.

Private Room Waterfront Access, sleeps 2

9.0 out of 10, Wonderful, (6)
"Property was secluded with a gated entrance. The grounds were beautiful and the waterfront area was magical. It had a very relaxing atmosphere and we didn't want to leave! Leslie was a fantastic hostess and we look forward to staying again in the future"
The price is ¥14,404
¥24,588 total
includes taxes & fees
Jun 29 - Jun 30
Private Room Waterfront Access, sleeps 2
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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