Experience the unique charm of Florida Keys, nestled in the scenic landscapes of Florida. Offering a variety of 8,923 cottages, find your home away from home here.

From cozy to lavish, Florida Keys offers a wide range of cottages to suit your budget and style. With prices starting from $39 and going up to $15,878, you’re spoilt for choice with amenities such as Air conditioner.

Top Features: Air conditioner, Internet / Wifi, Kitchen / Kitchenette, TV and Laundry

Local Highlights:

Begin your journey in Florida Keys today! Reserve your cottages and dive into the beauty and culture of Florida.

Top Cottages in Florida Keys

2 Bedroom Aqua Lodge # 13 Barracuda | Living area | Flat-screen TV
4.2
Excellent(139 Reviews)
Cottage
 in Big Pine Key
Old Wooden Bridge Resort and Marina
Pool · Pets allowed · Kitchen / Kitchenette

Discover the beauty of Florida Keys with a stay at Old Wooden Bridge Resort and Marina, a top rated Cottage with amenities such as Air conditioner, Internet / Wifi and Pets allowed, and more.

$$$$
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Outdoor dining
4.9
Outstanding(194 Reviews)
Cottage
 in Key West
PINEAPPLE COTTAGE: 2BR/2BA-Pvt Pool -1/2 block to Duval- RealKeyWest
5 guests · 2 bedrooms · 2 baths
Pool · Kitchen / Kitchenette · Air conditioner

Business stays, family stays, couples stay, getaway vacation, and rental in Florida Keys at PINEAPPLE COTTAGE: 2BR/2BA-Pvt Pool -1/2 block to Duval- RealKeyWest for $773 for your next trip.

$$$$
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Interior
Cottage
 in Key West
Tumi's Time Out by Avantstay Heart Of Old Town w/ Shared Pool Month Long Stays Only
Pool · Kitchen / Kitchenette · Air conditioner

Business stays, family stays, couples stay, getaway vacation, and rental in Florida Keys at Tumi's Time Out by Avantstay Heart Of Old Town w/ Shared Pool Month Long Stays Only for $260 for your next trip.

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Pool
4.9
Outstanding(198 Reviews)
Cottage
 in Cudjoe Key
**TIDEWATER VIEWS @ VENTURE OUT** 2BR/2BA Cottage + 35’ Private Slip | 80’ Pool
6 guests · 2 bedrooms · 2 baths
Pool · Pets allowed · Kitchen / Kitchenette

Indulge in a peaceful retreat at **TIDEWATER VIEWS @ VENTURE OUT** 2BR/2BA Cottage + 35’ Private Slip | 80’ Pool, our elegant Cottage in Florida Keys. Enjoy amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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Interior
Cottage
 in Key West
Cottage by the Pool by Avantstay w/ Balcony, BBQ & Shared Pool! Month Long Stays Only
Pool · Kitchen / Kitchenette · Air conditioner

Soak up the beauty of Florida Keys in our Cottage, Cottage by the Pool by Avantstay w/ Balcony, BBQ & Shared Pool! Month Long Stays Only. With a range of amenities such as Air conditioner, Dishwasher and Internet / Wifi, you'll feel right at home.

$$$$
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Terrace/patio
4.9
Outstanding(186 Reviews)
Cottage
 in Duck Key
3BR/3BA Sunset Cottage located at The Villages of Hawks Cay
8 guests · 3 bedrooms · 3 baths
Garden · Pool · Kitchen / Kitchenette

Indulge in a peaceful retreat at 3BR/3BA Sunset Cottage located at The Villages of Hawks Cay , our elegant Cottage in Florida Keys. Enjoy amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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Interior
Cottage
 in Key West
Beach House Condo by Avantstay Communal Pool Gated Community Great Location Week Long Stays
Pool · Kitchen / Kitchenette · Air conditioner

Looking to create some memories in Florida Keys? Look no further than our Cottage, Beach House Condo by Avantstay Communal Pool Gated Community Great Location Week Long Stays. Enjoy top-rated amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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A heated pool
5.0
Outstanding(199 Reviews)
Cottage
 in Key West
~ Chick-A-Pea Cottage ~ Enjoy Key West’s charisma, with a pool, and parking!
8 guests · 4 bedrooms · 3 baths
Garden · Pool · Pets allowed

Experience the best of Florida Keys with this Cottage available for $1,238. This property is equipped with amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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Interior
Cottage
 in Key West
Coral Breeze by Avantstay Close to Beach w/ Balcony & Shared Pool! Month Long Stays Only
Pool · Pets allowed · Kitchen / Kitchenette

Looking for a memorable stay in Florida Keys? Our Cottage might just be what you're looking for. Enjoy amenities including Air conditioner, Dishwasher and Internet / Wifi, and more during your stay.

$$$$
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Beach nearby, beach towels
5.0
Outstanding(174 Reviews)
Cottage
 in Key West
Sea Breeze Cottage with 2 Large Decks in Beautiful Truman Annex
6 guests · 3 bedrooms · 2 baths
Garden · Pool · Kitchen / Kitchenette

Experience vacation in Florida Keys with our Cottage, Sea Breeze Cottage with 2 Large Decks in Beautiful Truman Annex . Enjoy amenities such as Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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Interior
Cottage
 in Key West
Duval Sea Turtle by Avantstay Great Location Close to Shops Shared Pool!
Pool · Kitchen / Kitchenette · Air conditioner

Nestled in Florida Keys, this Cottage is perfect for your next vacation. Enjoy Duval Sea Turtle by Avantstay Great Location Close to Shops Shared Pool!'s top-rated amenities, including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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Pool
4.8
Outstanding(173 Reviews)
Cottage
 in Marathon
Authentic And Charming Little Cottage 60 Ft From The Ocean
2 guests · 1 bedroom · 1 bath
Garden · Pool · Kitchen / Kitchenette

Soak up the beauty of Florida Keys in our Cottage, Authentic And Charming Little Cottage 60 Ft From The Ocean. With a range of amenities such as Air conditioner, Internet / Wifi and Laundry, you'll feel right at home.

$$$$
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Vacation rentals with air conditioning in Florida Keys

Fridge, microwave, oven, stovetop
4.7
Outstanding(203 Reviews)
Cottage
 in Key West
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK
2 guests · 1 bedroom · 2 baths
Pets allowed · Kitchen / Kitchenette · Air conditioner

Enjoy the best of Florida Keys in our Cottage, Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK. A stunning property with amenities including Air conditioner, Internet / Wifi and Laundry, and more.

$$$$
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TV, DVD player, stereo
4.8
Outstanding(159 Reviews)
Cottage
 in Key West
Ann Street Cottage: A bright and airy home near Duval Street
2 guests · 1 bedroom · 2 baths
Pool · Kitchen / Kitchenette · Air conditioner

Business stays, family stays, couples stay, getaway vacation, and rental in Florida Keys at Ann Street Cottage: A bright and airy home near Duval Street for $480 for your next trip.

$$$$
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Fridge, microwave, oven, stovetop
4.8
Outstanding(147 Reviews)
Cottage
 in Key West
CONCH COTTAGE: Old Town - Hot Tub - 1 Block from Duval - 1BD/1BA RealKeyWest
2 guests · 1 bedroom · 1 bath
Pets allowed · Kitchen / Kitchenette · Air conditioner

Looking for a memorable stay in Florida Keys? Our Cottage might just be what you're looking for. Enjoy amenities including Air conditioner, Dishwasher and Internet / Wifi, and more during your stay.

$$$$
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Exterior
5.0
Outstanding(118 Reviews)
Cottage
 in Key West
**DARLING OF DUVAL @ OLD TOWN** Estate Cottage + Spa + LAST KEY SERVICES…
4 guests · 2 bedrooms · 2 baths
Kitchen / Kitchenette · Air conditioner · Internet / Wifi

The best choice in Florida Keys for Cottage, for $703 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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A heated pool
4.8
Outstanding(136 Reviews)
Cottage
 in Key west
Colony Poolside: A charming bungalow near Duval Street
2 guests · 1 bedroom · 1 bath
Garden · Pool · Kitchen / Kitchenette

Nestled in Florida Keys, this Cottage is perfect for your next vacation. Enjoy Colony Poolside: A charming bungalow near Duval Street's top-rated amenities, including Air conditioner, Internet / Wifi and Balcony / Patio, and more.

$$$$
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Exterior
5.0
Outstanding(100 Reviews)
Cottage
 in Key West
Heart of Downtown Key West Cottage With Off-Street Parking
3 guests · 2 bedrooms · 1 bath
Kitchen / Kitchenette · Air conditioner · Internet / Wifi

Looking for a Cottage in Florida Keys, this Cottage for $392 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.

$$$$
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Beach towels
5.0
Outstanding(101 Reviews)
Cottage
 in Islamorada
WATERFRONT KEYS COTTAGE GREAT RATES ! Walking distance to world famous Lorelei
2 guests · 1 bedroom · 1 bath
Garden · Pets allowed · Kitchen / Kitchenette

Indulge in a peaceful retreat at WATERFRONT KEYS COTTAGE GREAT RATES ! Walking distance to world famous Lorelei, our elegant Cottage in Florida Keys. Enjoy amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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Pool
4.6
Outstanding(139 Reviews)
Cottage
 in Key West
Conch Republic Consul General's Cottage.-Historic District
6 guests · 2 bedrooms · 2 baths
Garden · Pool · Kitchen / Kitchenette

When traveling to Florida Keys, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $394 per night.

$$$$
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Lake
5.0
Outstanding(95 Reviews)
Cottage
 in Islamorada
RELAX in your PRIVATE Oceanfront Cottage!
4 guests · 1 bedroom · 1 bath
Pets allowed · Kitchen / Kitchenette · Air conditioner

This inviting Cottage in Florida Keys can fit your needs for many types of vacations, at $277 per night.

$$$$
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Property grounds
4.8
Outstanding(101 Reviews)
Cottage
 in Key West
Colony Sunset- Bright and airy cottage in the heart of old town Key West
4 guests · 1 bedroom · 1 bath
Garden · Pool · Pets allowed

Discover the beauty of Florida Keys with a stay at Colony Sunset- Bright and airy cottage in the heart of old town Key West, a top rated Cottage with amenities such as Air conditioner, Internet / Wifi and Pets allowed, and more.

$$$$
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Beach nearby
4.9
Outstanding(100 Reviews)
Cottage
 in Key West
Southernmost Retreat: 2 Blocks from Duval in Old Town.
6 guests · 3 bedrooms · 2 baths
Pets allowed · Kitchen / Kitchenette · Air conditioner

Looking for a memorable stay in Florida Keys? Our Cottage might just be what you're looking for. Enjoy amenities including Air conditioner, Internet / Wifi and Pets allowed, and more during your stay.

$$$$
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A heated pool
4.8
Outstanding(96 Reviews)
Cottage
 in Cudjoe Key
Location, location, location briefly describes this small piece of Paradise.
4 guests · 2 bedrooms · 1 bath
Garden · Pool · Kitchen / Kitchenette

Are you ready to indulge in a relaxing getaway? Our Cottage in Florida Keys has everything you need for a rejuvenating stay. Treat yourself to Location, location, location briefly describes this small piece of Paradise. 's exceptional amenities, such as Air conditioner, Dishwasher and Internet / Wifi.

$$$$
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