Holiday Homes in Florida Keys

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Featured Holiday Homes in Florida Keys

Aqua Lodge Rentals At Coconut Cay

3.5 star property
9.6 out of 10, Exceptional, (130)
"Very unique family experience. Kids loved it and the property managers were very kind and helpful. Property was clean and well taken care of. We definitely plan to return in the future. "
The price is AU$541
includes taxes & fees
5 Jan - 6 Jan
Aqua Lodge Rentals At Coconut Cay

Finest location in Coral Lagoon. End unit with bay views and boat slip!

9.6 out of 10, Exceptional, (167)
"Great relaxed location in the Florida Keys. Only short 1 hr. 15 minutes ride to Key West. Beautiful townhouse with "
Finest location in Coral Lagoon. End unit with bay views and boat slip!

Old Florida Style, wrap around porch, boat basin for dockage, open water

9.8 out of 10, Exceptional, (61)
"Our family of five adults and a dog had a fantastic week at this beautiful house! We had plenty of space, it was super clean and well kept. The countertop ice maker was definitely appreciated! We didn’t cook but all the tools you could need are there. We did place an Instacart order from Publix for a few things and delivery was no problem. Lots of restaurants are within a short drive and Kiki’s right down the road was a plus and had great food. We spent most mornings and evenings hanging out on...
Old Florida Style, wrap around porch, boat basin for dockage, open water

Beachside @ Torchview Waterfront Retreat

9.8 out of 10, Exceptional, (37)
"I had a wonderful 3 weeks stay at Beachside@Torchview. I loved the privacy of the house, the gorgeous sunset views, and the peaceful mornings sitting out on the deck while drinking my morning coffee. I would highly recommend this house for anyone looking for a quiet getaway in the busy Florida Keys. It was everything I had hoped for, and I will definitely be staying here again if I decide to return to the Keys next year. The house was very clean and suited my needs perfectly, and the host...
Beachside @ Torchview Waterfront Retreat

P22 - Updated 3 bedroom 2 bath duplex with private pool and deep water dockage.

9.4 out of 10, Exceptional, (16)
"It was a nice place to stay. The best about this house other than the location that it has 3 bedrooms with King/King/Queen which works perfectly for adults. House was clean, check in easy, great location, close to Key Colony Club. Enough parking for 3 cars. Nice pool"
P22 - Updated 3 bedroom 2 bath duplex with private pool and deep water dockage.

Tipsy Turtle: Luxurious Waterfront Villa on Duck Key with Stunning Views and Modern Upgrades!

9.8 out of 10, Exceptional, (19)
"We visited this property for an extended weekend over the Thanksgiving holiday. Upon arrival we encountered a minor setback with a missing bathroom mirror, however, the property management company was very responsive and had someone on site to replace on Thanksgiving day AND without hesitation. Overall, the property was in a great location and as described. They even included Keurig cups for coffee.I appreciate the level of cleanliness and response time!"
Tipsy Turtle: Luxurious Waterfront Villa on Duck Key with Stunning Views and Modern Upgrades!

Sip Slidin' Hideaway: Key Colony 3BR/2BA pool with slide and boat dockage

Sip Slidin' Hideaway: Key Colony 3BR/2BA pool with slide and boat dockage

VOTED BEST KEY LARGO VACATION RENTAL

10.0 out of 10, Exceptional, (69)
"The townhome was large and I liked the layout so everyone had their own space. There are multiple balconies which was one of our favorite places to hang out while there. The sunrise/sunsets at the beach were beautiful! We were busy so didn’t spend much time in the lagoon or pools but the grounds were well-kept. "
VOTED BEST KEY LARGO VACATION RENTAL

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

10.0 out of 10, Exceptional, (43)
"The townhouse was great for our family and in a perfect location to explore the upper keys. "
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool

Manatee Bay: Escape to this 2BR Duck Key Villa, Private Patio, Dip Pool & Easy Access to Marathon

9.8 out of 10, Exceptional, (21)
"Everything was just as advertise. Tina, the host, was great, responsive, and gave us some ideas of where to eat. I recommend this unit. Hope to go bac soon! "
Manatee Bay: Escape to this 2BR Duck Key Villa, Private Patio, Dip Pool & Easy Access to Marathon

PRIVATE WATERFRONT HOUSE DOCK 4KAYAKS 2SUP BOARD GOLF CART

10.0 out of 10, Exceptional, (135)
"We loved this house! Plenty of room, wonderful location. Super clean and the outdoor space was awesome! Hot tub, BBQ and plenty of toys to enjoy the lagoon❤️"
The price is AU$1,859
includes taxes & fees
28 Jan - 29 Jan
PRIVATE WATERFRONT HOUSE DOCK 4KAYAKS 2SUP BOARD GOLF CART

Comfort and Relaxation! Balcony, Free Parking, Pool, Pet-friendly Property

The price is AU$706
includes taxes & fees
16 Jan - 17 Jan
Comfort and Relaxation! Balcony, Free Parking, Pool, Pet-friendly Property

Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes

9.8 out of 10, Exceptional, (219)
"Perfect location with sunset views and kayaking "
The price is AU$1,219
includes taxes & fees
7 Jan - 8 Jan
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes

3 night minimum! Spectacular Ocean Views!

8.4 out of 10, Very good, (18)
"Venture out is a great location for being on the water. This rental was reasonable, spacious and clean! We had an amazing stay with no issues!"
3 night minimum! Spectacular Ocean Views!

Tropical Retreat at Coral Lagoon ~ Waterfront Luxury Villa w/ Pool!

9.2 out of 10, Wonderful, (52)
"Vwry nice house with everything you need in the heart of the keys."
Tropical Retreat at Coral Lagoon ~ Waterfront Luxury Villa w/ Pool!

Last Minute Discounts! Deep Water Canal w/ Pool, Walk to Ocean Front Tiki Bars!

10.0 out of 10, Exceptional, (147)
"We loved our stay at the twin dolphin. The place is exactly as it is described on VRBO. It was close to many awesome spots, although walkers take your life in your hands on the highway. Beds were comfortable but small for queens. Great dock to fish and people watch and the swim spa was great! Only 2 small beefs… there was never enough hot water and the cleaning crew working outside filled every trash can leaving us no place to put checkout trash. . "
Last Minute Discounts! Deep Water Canal w/ Pool, Walk to Ocean Front Tiki Bars!

Walk to Beach, Open Water View from porch , dock, bikes, kayaks & snorkel gear

9.8 out of 10, Exceptional, (108)
"This place was beautiful. When staying in a rental, there can always be a little something that is not right or goes wrong. Nothing went wrong with this place. The master bed evidently has an older form top mattress that doesn't dissipate heat, so it you are warm sleeping you will want to sleep in the second bedroom. It's not quite as bad. You may want to bring your own King Sheets and pillowcases. They were very rough!! All in all, I would recommend this place! They seemed to have everything...
Walk to Beach, Open Water View from porch , dock, bikes, kayaks & snorkel gear

Waterfront villa with 5 kayaks, covered deck, washer/dryer, & AC

8.8 out of 10, Excellent, (20)
"Very happy with our stay. Celebrated our 10 year wedding anniversary. Relaxing, quiet, peaceful, and welcoming. Would definitely stay again. Loved the use of the kayaks."
Waterfront villa with 5 kayaks, covered deck, washer/dryer, & AC

Coral Lagoon Single Family Home 3bed/2.5bath with 40' Boat Slip w/ Power + Water

9.8 out of 10, Exceptional, (86)
"Everything was clean and easy check in. Thank Jeff for a wonderful stay!"
Coral Lagoon Single Family Home 3bed/2.5bath with 40' Boat Slip w/ Power + Water

811 Mariners Club Key Largo | 4 Bed, 3 Bath

9.6 out of 10, Exceptional, (87)
"The rental was great and so was the whole property/community at Mariners! The duplex was perfect for our multi-generational vacation: 2 couples with kids plus the grandparents. The kids loved the several board games the house had and the parents loved the screened, fanned porch. Property manager Michael reached out and was available over text. The lagoon pool was magnificent, especially great for toddlers/young kids, with an expansive wade-in area and a sandy area too. I have nothing negative to...
811 Mariners Club Key Largo | 4 Bed, 3 Bath
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 Florida Keys

Breezy Palms Resort

2.5 star property
8.6 out of 10, Excellent, (386)
"Amazing place to stay and right near everything. Very authentic."
The price is AU$253
includes taxes & fees
5 Jan - 6 Jan
Breezy Palms Resort

Skipjack Resort & Marina

3.0 star property
8.6 out of 10, Excellent, (1141)
"We love staying at this property because it’s just like an apartment with all the comforts of home."
The price is AU$600
includes taxes & fees
6 Jan - 7 Jan
Skipjack Resort & Marina

Aqua Lodge Rentals At Coconut Cay

3.5 star property
9.6 out of 10, Exceptional, (130)
"Very unique family experience. Kids loved it and the property managers were very kind and helpful. Property was clean and well taken care of. We definitely plan to return in the future. "
The price is AU$541
includes taxes & fees
5 Jan - 6 Jan
Aqua Lodge Rentals At Coconut Cay
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.