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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Condo Rentals in Windley Key

Mariners Club Oceanfront Condo, Water views from every room, Tennis & Pickleball
Relax by the resort's oval-shaped pool surrounded by palm trees and lounge chairs.

Mariners Club Oceanfront Condo, Water views from every room, Tennis & Pickleball

10.0 out of 10, Exceptional, (125)
"We had an excellent stay! The property and all the added touches made our stay relaxing and low stress. The host was engaging and helpful if we had questions. We would stay here again!"
Mariners Club Oceanfront Condo, Water views from every room, Tennis & Pickleball
Aug-Sept Deals! OCEANFRONT Lux 1300sf w/ Stunning Views & All Amenities of home!
Relax in two Adirondack chairs on a shaded deck overlooking the ocean.

Aug-Sept Deals! OCEANFRONT Lux 1300sf w/ Stunning Views & All Amenities of home!

9.6 out of 10, Exceptional, (287)
"Visited with my Mother, sister and cousin. Felt very safe with the gated security. The grounds were beautiful and very well maintained. Location was great! The beach, marina, pool were all very close by. And the condo was fabulous and very well stocked."
Aug-Sept Deals! OCEANFRONT Lux 1300sf w/ Stunning Views & All Amenities of home!
Mariners Club 114, Amazing Location & Views, Epic Amenities, Indoor Pickleball
Relax by the resort's large pool surrounded by palm trees and lounge chairs.

Mariners Club 114, Amazing Location & Views, Epic Amenities, Indoor Pickleball

10.0 out of 10, Exceptional, (31)
"Clean and easy to book. Great location for a nice fishing trip. Owner wonderful to work with and provide locale information that was very helpful. "
Mariners Club 114, Amazing Location & Views, Epic Amenities, Indoor Pickleball
Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo
Relax by the pool surrounded by lush greenery and lounge under shaded umbrellas.

Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo

9.8 out of 10, Exceptional, (219)
"Condo was clean and quiet. Loved the main suite in the back."
The price is AU$644
includes taxes & fees
17 Aug - 18 Aug
Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo
Ocean Front Private Beach, Pool/Hot Tub, Pool Bar, Marina with Cafe
Enjoy waterfront views and access to the water from this property, surrounded by lush greenery and palm trees.

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

9.8 out of 10, Exceptional, (185)
"Nice place, lots to do, great location, great views"
Ocean Front Private Beach, Pool/Hot Tub, Pool Bar, Marina with Cafe
Kawama Yacht Club - 2 Bedrooms with a Private Ocean Front Beach
Relax in style with Adirondack chairs on the beach, surrounded by a tranquil ocean view.

Kawama Yacht Club - 2 Bedrooms with a Private Ocean Front Beach

9.8 out of 10, Exceptional, (133)
"The property is older but was clean and orderly. Good access to the rest of the city. First time staying in Key Largo so can’t gauge the property against others. "
Kawama Yacht Club - 2 Bedrooms with a Private Ocean Front Beach
Coastal Luxury: Key Largo 2BR Condo w/ Lagoon, Golf Cart, Pools & Amenities
Relax under the shade of this beachside structure, surrounded by comfortable seating and a stunning ocean view.

Coastal Luxury: Key Largo 2BR Condo w/ Lagoon, Golf Cart, Pools & Amenities

10.0 out of 10, Exceptional, (11)
Coastal Luxury: Key Largo 2BR Condo w/ Lagoon, Golf Cart, Pools & Amenities
Condo with Pool and Beach Access
Relax on the deck overlooking the serene water with comfortable seating and a ceiling fan for a peaceful atmosphere.

Condo with Pool and Beach Access

10.0 out of 10, Exceptional, (21)
"We liked everything about the property. This is a quite end unit and was nicely finished. Would definitely highly recommend staying here."
Condo with Pool and Beach Access
Relax in your one bedroom Oceanfront Suite in Tavernier FL. Florida Keys.
Relax by the pool surrounded by palm trees and lounge chairs.

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

9.6 out of 10, Exceptional, (54)
"Very nice"
Relax in your one bedroom Oceanfront Suite in Tavernier FL. Florida Keys.
Mariners Club 316 Oceanfront Condo, Private Gym, Epic Amenities, Pickleball
Relax in a shaded seating area overlooking the water, surrounded by a thatched roof and comfortable benches.

Mariners Club 316 Oceanfront Condo, Private Gym, Epic Amenities, Pickleball

10.0 out of 10, Exceptional, (33)
"Great place to take your family and enjoy doing nothing but relaxing by the pool or on the beach. "
Mariners Club 316 Oceanfront Condo, Private Gym, Epic Amenities, Pickleball
Relaxed Boho Vibes & Views [ Ocean Pointe 2315]
Relax by the serene pool surrounded by lush greenery and tall palm trees.

Relaxed Boho Vibes & Views [ Ocean Pointe 2315]

9.8 out of 10, Exceptional, (172)
"Enjoyed our stay. Highlighted by day trips to Key West, snorkeling with Robbie’s, and seeing a manatee while kayaking in John Pennekamp State Park. Property has nice beach area and pool. "
Relaxed Boho Vibes & Views [ Ocean Pointe 2315]
Key Largo-Islamorada area-1 BR, 1 Bath -Privately Owned Condo -Fab Reviews!
Enjoy waterfront views and access to a dock and boat.

Key Largo-Islamorada area-1 BR, 1 Bath -Privately Owned Condo -Fab Reviews!

10.0 out of 10, Exceptional, (170)
"Very nice, close to the pool, nice amenities, close to tons of great food options."
Key Largo-Islamorada area-1 BR, 1 Bath -Privately Owned Condo -Fab Reviews!
Gorgeous oceanfront retreat with marina, pool, & ocean views
Relax by the serene pool surrounded by palm trees and lounge chairs.

Gorgeous oceanfront retreat with marina, pool, & ocean views

9.0 out of 10, Wonderful, (68)
"I love that this resort had its own private Beach area, pier, restaurant, and pool area!"
The price is AU$685
includes taxes & fees
11 Aug - 12 Aug
Gorgeous oceanfront retreat with marina, pool, & ocean views
Ocean View Suite, Top Floor, Updated
Relax on the beach with comfortable lounge chairs and enjoy the ocean views from a nearby pier.

Ocean View Suite, Top Floor, Updated

10.0 out of 10, Exceptional, (79)
"This was a wonderful base of operations for our family vacation in the Keys!"
Ocean View Suite, Top Floor, Updated
Key Largo hidden gem!! Rare Moon Bay condo with 2.5 baths!!
Relax by the oceanfront pool surrounded by palm trees and lounge chairs.

Key Largo hidden gem!! Rare Moon Bay condo with 2.5 baths!!

10.0 out of 10, Exceptional, (39)
"We had a very nice stay - easy checkin, very clean condo unit, condo grounds were very clean with lots to do. Location was also nice - convenient to parks and restaurants. Would definitely recommend! "
Key Largo hidden gem!! Rare Moon Bay condo with 2.5 baths!!
OCEANFRONT COMMUNITY, LUXURY,BEACH,POOLS, TOP AMENITIES & VALUE in FLORIDA KEYS
Relax on the beachside deck with a shaded seating area and ocean views.

OCEANFRONT COMMUNITY, LUXURY,BEACH,POOLS, TOP AMENITIES & VALUE in FLORIDA KEYS

10.0 out of 10, Exceptional, (192)
"Great condo! Great location! A clean, quiet and serene vacation destination, but yet very convenient to the other places we wanted to visit. Owners were very thoughtful and communicative. Highly recommend!"
OCEANFRONT COMMUNITY, LUXURY,BEACH,POOLS, TOP AMENITIES & VALUE in FLORIDA KEYS
Oceanfront Property with Elevator, Lagoon and 2 Heated Pools
Relax by the ocean with a warm fire and comfortable seating.

Oceanfront Property with Elevator, Lagoon and 2 Heated Pools

9.6 out of 10, Exceptional, (151)
"We stayed for a week. Wonderful condo and resort."
Oceanfront Property with Elevator, Lagoon and 2 Heated Pools
Luxury Condo at Ocean Front Kawama Tower Complex
Relax in a casual beachside seating area surrounded by a thatched-roof structure and Adirondack chairs.

Luxury Condo at Ocean Front Kawama Tower Complex

9.4 out of 10, Exceptional, (55)
"Very clean and spacious condo. Pool area very quiet and relaxing - no crowds. Enjoyed the pickle ball courts. Quick drive to restaurants."
Luxury Condo at Ocean Front Kawama Tower Complex
Island Getaway at Ocean Point
Relax on the deck with Adirondack chairs and a small table, overlooking a serene body of water.

Island Getaway at Ocean Point

9.8 out of 10, Exceptional, (49)
"Host was great. Place was clean. Location was perfect. "
Island Getaway at Ocean Point
Updated ocean-view condo with 2 balconies, pool, hot tub, W/D, & AC
Relax on the deck overlooking the serene water, surrounded by comfortable seating and a ceiling fan for a tranquil atmosphere.

Updated ocean-view condo with 2 balconies, pool, hot tub, W/D, & AC

9.8 out of 10, Exceptional, (31)
"Fabulous stay- we will be back!"
Updated ocean-view condo with 2 balconies, pool, hot tub, W/D, & AC
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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