Key West Cottage Rentals

KAYAK searches hundreds of travel sites at once for cottage deals in Key West

Here is why travelers choose KAYAK

Free to useThere are no hidden charges or fees.

Filter your dealsFilter by free cancellation, free breakfast and more.

Millions of reviewsCheck ratings based on millions of real guest reviews.

Recommended by KAYAK
Booking Insights
Recommended by KAYAK

Best Key West cottage rentals

Go to map

Search by review score

6+ Okay7+ Good8+ Great9+ Excellent

Search by price

$118 - $560$560 - $1,001$1,001 - $1,442$1,442 - $1,883$1,883+ per night

Search by freebies

Free breakfastFree parkingFree cancellationFree internetFree airport shuttle

Most recommended cottage rentals in Key West

Show all
Ann Street Tranquility: A cozy and peaceful cottage - Key West - Living room
Ann Street Tranquility: A cozy and peaceful cottage
Old Town North of Truman
9.8Wonderful(33)
Cottage
Free Wi-Fi
$864+
Check availability
The Dancing Rooster: 2 Blocks from Duval in Old Town. - Key West - Beach
The Dancing Rooster: 2 Blocks from Duval in Old Town.
Downtown
9.8Wonderful(88)
Cottage
Free Wi-Fi
$906+
Check availability
Duval Breeze by AvantStay Great Location Close to Beach Nightlife Shared Pool Week Long Stays - Key West - Living room
Duval Breeze by AvantStay Great Location Close to Beach Nightlife Shared Pool Week Long Stays
Old Town South of Truman
8.7Very good(26)
Cottage
Parking
Free Wi-Fi
Pool
$921+
Check availability
Paradise Place by AvantStay Key West Old Town Condo w Shared Pool - Key West - Living room
Paradise Place by AvantStay Key West Old Town Condo w Shared Pool
The Meadows
8.4Very good(30)
Cottage
Free Wi-Fi
Pool
Pet friendly
$624+
Check availability
Tranquility By Avantstay Close To Duval - Key West - Living room
Tranquility By Avantstay Close To Duval
Downtown
8.6Very good(20)
Cottage
Free Wi-Fi
$715+
Check availability
Tennessee Williams by Avantstay Funky Design + Pool - Key West - Living room
Tennessee Williams by Avantstay Funky Design + Pool
Downtown
Cottage
Free Wi-Fi
$264+
Check availability
Lighthouse Villa by Avantstay Walk to Southernmost Point w/ Private Pool & Patio Month Long Stays - Key West - Balcony
Lighthouse Villa by Avantstay Walk to Southernmost Point w/ Private Pool & Patio Month Long Stays
Downtown
Cottage
Free Wi-Fi
$521+
Check availability
Oasis in Old Town - our special home - Key West - Pool
Oasis in Old Town - our special home
Downtown
Cottage
Free Wi-Fi
$284+
Check availability
Coral Palm by Avantstay Key West Walkable Gated Community & Shared Pool - Key West - Balcony
Coral Palm by Avantstay Key West Walkable Gated Community & Shared Pool
Golf Club
Cottage
Free Wi-Fi
$846+
Check availability
Hidden Oasis Colony - Key West - Patio
Hidden Oasis Colony
Downtown
9.9Wonderful(22)
Cottage
Parking
Free Wi-Fi
Pet friendly
Spa
$875+
Check availability
Eyebrow Suite - 2bd/1.5ba Suite off Duval - Key West - Pool
Eyebrow Suite - 2bd/1.5ba Suite off Duval
Downtown
9.6Wonderful(40)
Cottage
$937+
Check availability
Colony Calypso - A quaint 1 Bedroom Cottage just two blocks to Duval - Key West - Beach
Colony Calypso - A quaint 1 Bedroom Cottage just two blocks to Duval
Downtown
9.5Wonderful(36)
Cottage
Free Wi-Fi
$801+
Check availability
Island Style Colony - Key West - Pool
Island Style Colony
Downtown
9.5Wonderful(34)
Cottage
Parking
Free Wi-Fi
Pool
Pet friendly
$722+
Check availability
Osprey Studio @ The Colony-Sleeps Up To 4 - Key West - Pool
Osprey Studio @ The Colony-Sleeps Up To 4
Downtown
9.1Wonderful(9)
Cottage
Free Wi-Fi
$747+
Check availability
Pineapple Cottage ~ Adorable, Updated Old Town Cottage W/ Shared Heated Pool! - Key West - Living room
Pineapple Cottage ~ Adorable, Updated Old Town Cottage W/ Shared Heated Pool!
Truman Annex
9.5Wonderful(12)
Cottage
Free Wi-Fi
$184+
Check availability
Tropical Dreaming By Avantstay 4 Blks To Beach Private Pool - Key West
Tropical Dreaming By Avantstay 4 Blks To Beach Private Pool
Old Town South of Truman
9.3Wonderful(27)
Cottage
Parking
Free Wi-Fi
Pool
Pet friendly
$1,317+
Check availability
Booking Insights

KAYAK’s Insights for cottages in Key West

Discover seasonal trends, ideal booking windows, and other data-driven tips to plan your stay in Key West with confidence.

Which month has the cheapest cottage rates in Key West?

Cottages are cheapest in Key West in August, with average rates of $96/night. In comparison, December is the most expensive month, with prices at $1,233/night.

What is the cheapest day of the week to book a cottage in Key West?

Tuesday offers the lowest rates in Key West, with an average nightly price of $257/night. The highest prices are found on Saturday, with average rates at $1,010/night.

Which neighbourhood do KAYAK users most love to book their cottage in Key West?

The most popular neighbourhood in Key West among KAYAK users to search for a cottage is Downtown, with an average price of $775. The Palms Hotel, Truman Hotel, and Winslow's Bungalows - Key West Historic Inns rank among the highest-rated hotels in Downtown.

Find deals

Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

August
December
$598
$767
Cheapest month to stay with an average 85% drop in price.
Most expensive month to stay with an average 89% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

KAYAK's top tips for finding Key West vacation rental deals

  • For the cheapest cottage rental in Key West, try to visit during the low season and outside of main travel peaks. The cheapest rates can be found in August and November.
  • The cheapest night of the week to rent a cottage in Key West is Tuesday. On the other hand, the most expensive is Saturday.

FAQs when Booking a cottage in Key West

  • How much is a cottage rental for a month in Key West?

    The average price for a monthly Key West cottage rental found by KAYAK users in the last 2 weeks is $22,457 ($749/night).

Where to stay in Key West?

Our map will help you find the perfect place to stay in Key West by showing you the exact location of each vacation rental.

Everything you need to know for your stay in Key West

Hotels near airports in Key West

Hotels near Key West Airport