Vacation rentals in Key West, FL

Best Vacation rentals and Airbnb offers in Key West, FL

Salvador's Seclusion | Cozy Studio Retreat w/ Heated Pool

Apartment, Key West

Salvador's Seclusion · Cozy Studio Retreat w/ Heated Pool is a apartment in Key West, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a comfortable base…

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About Salvador's Seclusion | Cozy Studio Retreat w/ Heated Pool

Salvador's Seclusion · Cozy Studio Retreat w/ Heated Pool is a apartment in Key West, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,241.

From$177/night

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Andy's Attic | Budget-Friendly!

Apartment, Key West

Andy's Attic · Budget-Friendly! is a apartment in Key West, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Andy's Attic | Budget-Friendly!

Andy's Attic · Budget-Friendly! is a apartment in Key West, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,250.

From$179/night

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The Curry Poolside | Ground Floor King

Apartment, Key West

The Curry Poolside · Ground Floor King is a apartment in Key West, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About The Curry Poolside | Ground Floor King

The Curry Poolside · Ground Floor King is a apartment in Key West, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, pet friendly, pets friendly, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,333.

From$190/night

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Carey's Corner | Updated Studio with Heated Pool

Apartment, Key West

Carey's Corner · Updated Studio with Heated Pool is a apartment in Key West, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area,…

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About Carey's Corner | Updated Studio with Heated Pool

Carey's Corner · Updated Studio with Heated Pool is a apartment in Key West, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,364.

From$195/night

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Browse Vacation Rentals with a Pool in Key West, FL

Add a pool to the search when you want an easy place to cool off between outings.

Amsterdam's Curry Mansion Inn

Guest House, Key West

Amsterdam's Curry Mansion Inn is a guest house in Key West, with pool access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Amsterdam's Curry Mansion Inn

Amsterdam's Curry Mansion Inn is a guest house in Key West, with pool access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, parking, and van parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,711.

From$204/night

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The James Classic | Ground Floor King

Apartment, Key West

The James Classic · Ground Floor King is a apartment in Key West, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About The James Classic | Ground Floor King

The James Classic · Ground Floor King is a apartment in Key West, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,448.

From$207/night

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Oceanfront Oasis Smathers Beach Condo Sunrise views Island Charm Book today

Condo, Key West

Oceanfront Oasis Smathers Beach Condo Sunrise views Island Charm Book today is a condo in Key West, with pool access, easy beach access, and kitchen access. This stay gives travelers a…

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About Oceanfront Oasis Smathers Beach Condo Sunrise views Island Charm Book today

Oceanfront Oasis Smathers Beach Condo Sunrise views Island Charm Book today is a condo in Key West, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,043.

From$292/night

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Botanical Island Delight

Holiday Home, Key West

Botanical Island Delight is a holiday home in Key West, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

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About Botanical Island Delight

Botanical Island Delight is a holiday home in Key West, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,768.

From$294/night

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Best Key West, FL vacation rentals with parking

Find vacation rentals that make arriving by car easier.

The Bartlum - Steps to Duval Street

Apartment, Key West

The Bartlum - Steps to Duval Street is a apartment in Key West, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About The Bartlum - Steps to Duval Street

The Bartlum - Steps to Duval Street is a apartment in Key West, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and street parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,952.

From$279/night

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Caribbean House

B & B, Key West

Caribbean House is a b & b in Key West, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

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About Caribbean House

Caribbean House is a b & b in Key West, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free breakfast, free wifi, parking, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,411.

From$284/night

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Key West - Stock Island

Holiday Home, Key West

Key West - Stock Island is a holiday home in Key West, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Key West - Stock Island

Key West - Stock Island is a holiday home in Key West, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,083.

From$298/night

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Resort condo with pool & hot tub, private parking

Condo, Key West

Resort condo with pool & hot tub, private parking is a condo in Key West, with pool access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Resort condo with pool & hot tub, private parking

Resort condo with pool & hot tub, private parking is a condo in Key West, with pool access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,163.

From$309/night

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Best Pet-Friendly Vacation Rentals in Key West, FL

Bring your pet along with stays that welcome four-legged travelers.

The Curry Classic | Main Mansion King

Apartment, Key West

The Curry Classic · Main Mansion King is a apartment in Key West, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About The Curry Classic | Main Mansion King

The Curry Classic · Main Mansion King is a apartment in Key West, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,430.

From$204/night

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The Curry Classic | Main Mansion King

Apartment, Key West

The Curry Classic · Main Mansion King is a apartment in Key West, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About The Curry Classic | Main Mansion King

The Curry Classic · Main Mansion King is a apartment in Key West, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, pet friendly, pets friendly, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,430.

From$204/night

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The Curry Classic | Main Mansion King

Apartment, Key West

The Curry Classic · Main Mansion King is a apartment in Key West, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About The Curry Classic | Main Mansion King

The Curry Classic · Main Mansion King is a apartment in Key West, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, pet friendly, pets friendly, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,430.

From$204/night

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The Curry Poolside Suite | Second Floor King

Apartment, Key West

The Curry Poolside Suite · Second Floor King is a apartment in Key West, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area,…

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About The Curry Poolside Suite | Second Floor King

The Curry Poolside Suite · Second Floor King is a apartment in Key West, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, pet friendly, pets friendly, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,430.

From$204/night

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Best Key West, FL vacation rentals with a kitchen

Compare stays with kitchen access for longer trips and easier meals.

The Cat Island Suite | Charmingly Renovated w/ Pool

Condo, Key West

The Cat Island Suite · Charmingly Renovated w/ Pool is a condo in Key West, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About The Cat Island Suite | Charmingly Renovated w/ Pool

The Cat Island Suite · Charmingly Renovated w/ Pool is a condo in Key West, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,861.

From$266/night

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The Cayo Coco | Key West Condo with Pool, Hot Tub!

Condo, Key West

The Cayo Coco · Key West Condo with Pool, Hot Tub! is a condo in Key West, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a comfortable base for…

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About The Cayo Coco | Key West Condo with Pool, Hot Tub!

The Cayo Coco · Key West Condo with Pool, Hot Tub! is a condo in Key West, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,861.

From$266/night

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The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!

Condo, Key West

The Samana Cay · Tropical, Airy Retreat w/ Private Balcony, Pool! is a condo in Key West, with pet-friendly space, pool access, and outdoor space. This stay gives travelers a comfortable…

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About The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!

The Samana Cay · Tropical, Airy Retreat w/ Private Balcony, Pool! is a condo in Key West, with pet-friendly space, pool access, and outdoor space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,864.

From$266/night

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Comfortable Condo with Pool, Private Balcony, & Beach Access

Condo, Key West

Comfortable Condo with Pool, Private Balcony, & Beach Access is a condo in Key West, with pool access, easy beach access, and outdoor space. This stay gives travelers a comfortable base for…

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About Comfortable Condo with Pool, Private Balcony, & Beach Access

Comfortable Condo with Pool, Private Balcony, & Beach Access is a condo in Key West, with pool access, easy beach access, and outdoor space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,110.

From$301/night

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Our Favorite Family-Friendly Vacation Rentals in Key West, FL

Plan a trip with stays that give families more room to spread out.

The Bartlum-Luxurious Studio

Apartment, Key West

The Bartlum-Luxurious Studio is a apartment in Key West, with room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About The Bartlum-Luxurious Studio

The Bartlum-Luxurious Studio is a apartment in Key West, with room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, ac, air conditioning, family friendly, and family room.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,049.

From$250/night

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Freshly Renovated Cottage Old Town MONTHLY

Holiday Home, Key West

Freshly Renovated Cottage Old Town MONTHLY is a holiday home in Key West, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Freshly Renovated Cottage Old Town MONTHLY

Freshly Renovated Cottage Old Town MONTHLY is a holiday home in Key West, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: kitchen, with kitchen, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,325.

From$332/night

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Great Family Vacation Rental.

Holiday Home, Key West

Great Family Vacation Rental. is a holiday home in Key West, with pool access, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area,…

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About Great Family Vacation Rental.

Great Family Vacation Rental. is a holiday home in Key West, with pool access, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,867.

From$410/night

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Atlantic Paradise by Avantstay Great Location w/ Balcony, Outdoor Dining & Shared Pool & Hot Tub!

Cottage, Key West

Atlantic Paradise by Avantstay Great Location w/ Balcony, Outdoor Dining & Shared Pool & Hot Tub! is a cottage in Key West, with pool access, outdoor space, and kitchen access. This stay…

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About Atlantic Paradise by Avantstay Great Location w/ Balcony, Outdoor Dining & Shared Pool & Hot Tub!

Atlantic Paradise by Avantstay Great Location w/ Balcony, Outdoor Dining & Shared Pool & Hot Tub! is a cottage in Key West, with pool access, outdoor space, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,588.

From$469/night

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