Vacation rentals in Pigeon Key, FL

Best Vacation rentals and Airbnb offers in Pigeon Key, FL

Sea Glass Cottage~ Pet Friendly Tropical Home!

Holiday Home, Pigeon Key

Sea Glass Cottage~ Pet Friendly Tropical Home! is a holiday home in Pigeon Key, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the…

Read more

About Sea Glass Cottage~ Pet Friendly Tropical Home!

Sea Glass Cottage~ Pet Friendly Tropical Home! is a holiday home in Pigeon Key, with pet-friendly 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: free wifi, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,591.

From$227/night

Show›

Hidden Treasure near the 7mile

Holiday Home, Pigeon Key

Hidden Treasure near the 7mile is a holiday home in Pigeon Key, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

Read more

About Hidden Treasure near the 7mile

Hidden Treasure near the 7mile is a holiday home in Pigeon Key, with pet-friendly 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: pet friendly, pets friendly, kitchen, with kitchen, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,676.

From$239/night

Show›

Bob's Harbor View is a charming 2-bedroom, 2-bathroom retreat nestled near the picturesque Seven Mile Bridge.

Holiday Home, Pigeon Key

Bob's Harbor View is a charming 2-bedroom, 2-bathroom retreat nestled near the picturesque Seven Mile Bridge. is a holiday home in Pigeon Key, with pet-friendly space, kitchen access, and…

Read more

About Bob's Harbor View is a charming 2-bedroom, 2-bathroom retreat nestled near the picturesque Seven Mile Bridge.

Bob's Harbor View is a charming 2-bedroom, 2-bathroom retreat nestled near the picturesque Seven Mile Bridge. is a holiday home in Pigeon Key, with pet-friendly space, 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 wifi, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,696.

From$242/night

Show›

Welcome to Casa Carey — your laid-back Keys escape in Marathon! 🌴

Holiday Home, Pigeon Key

Welcome to Casa Carey — your laid-back Keys escape in Marathon! 🌴 is a holiday home in Pigeon Key, with parking and kitchen access. This stay gives travelers a comfortable base for…

Read more

About Welcome to Casa Carey — your laid-back Keys escape in Marathon! 🌴

Welcome to Casa Carey — your laid-back Keys escape in Marathon! 🌴 is a holiday home in Pigeon Key, 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 free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,823.

From$260/night

Show›

Browse Vacation Rentals with a Pool in Pigeon Key, FL

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

2/2 Pool Home on Sombrero Beach with screened porch-beautiful views

Holiday Home, Pigeon Key

2/2 Pool Home on Sombrero Beach with screened porch-beautiful views is a holiday home in Pigeon Key, with pool access, easy beach access, and kitchen access. This stay gives travelers a…

Read more

About 2/2 Pool Home on Sombrero Beach with screened porch-beautiful views

2/2 Pool Home on Sombrero Beach with screened porch-beautiful views is a holiday home in Pigeon Key, 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, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,463.

From$352/night

Show›

The Hammocks at Marathon

Holiday Home, Pigeon Key

The Hammocks at Marathon is a holiday home in Pigeon Key, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

Read more

About The Hammocks at Marathon

The Hammocks at Marathon is a holiday home in Pigeon Key, 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 gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,119.

From$371/night

Show›

Paradise House a Waterfront Oasis : Your Perfect Getaway on the Atlantic!

Holiday Home, Pigeon Key

Paradise House a Waterfront Oasis : Your Perfect Getaway on the Atlantic! is a holiday home in Pigeon Key, with pool access, easy beach access, and kitchen access. This stay gives travelers…

Read more

About Paradise House a Waterfront Oasis : Your Perfect Getaway on the Atlantic!

Paradise House a Waterfront Oasis : Your Perfect Getaway on the Atlantic! is a holiday home in Pigeon Key, 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, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,024.

From$432/night

Show›

Spectacular Gulf Front Home - Pool, Dock, Incredible Gulf View

Holiday Home, Pigeon Key

Spectacular Gulf Front Home - Pool, Dock, Incredible Gulf View is a holiday home in Pigeon Key, with pool access, easy beach access, and parking. This stay gives travelers a comfortable…

Read more

About Spectacular Gulf Front Home - Pool, Dock, Incredible Gulf View

Spectacular Gulf Front Home - Pool, Dock, Incredible Gulf View is a holiday home in Pigeon Key, with pool access, easy beach 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: pool, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,178.

From$454/night

Show›

Best Pigeon Key, FL vacation rentals with parking

Find vacation rentals that make arriving by car easier.

Inviting home near the water with gazebo, fire table, and heated spa

Holiday Home, Pigeon Key

Inviting home near the water with gazebo, fire table, and heated spa is a holiday home in Pigeon Key, with parking and kitchen access. This stay gives travelers a comfortable base for…

Read more

About Inviting home near the water with gazebo, fire table, and heated spa

Inviting home near the water with gazebo, fire table, and heated spa is a holiday home in Pigeon Key, 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, hot tub, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,622.

From$232/night

Show›

Perfect area for kayaking with screened porch, secluded area off Sombrero Beach

Holiday Home, Pigeon Key

Perfect area for kayaking with screened porch, secluded area off Sombrero Beach is a holiday home in Pigeon Key, with easy beach access, parking, and kitchen access. This stay gives…

Read more

About Perfect area for kayaking with screened porch, secluded area off Sombrero Beach

Perfect area for kayaking with screened porch, secluded area off Sombrero Beach is a holiday home in Pigeon Key, with easy beach 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: kitchen, with kitchen, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,078.

From$297/night

Show›

UPDATED, 4 BIKES 2 KAYAKS, WALK TO SOMBRERO BEACH!

Holiday Home, Pigeon Key

UPDATED, 4 BIKES 2 KAYAKS, WALK TO SOMBRERO BEACH! is a holiday home in Pigeon Key, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for…

Read more

About UPDATED, 4 BIKES 2 KAYAKS, WALK TO SOMBRERO BEACH!

UPDATED, 4 BIKES 2 KAYAKS, WALK TO SOMBRERO BEACH! is a holiday home in Pigeon Key, with easy beach 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: hot tub, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,089.

From$298/night

Show›

W15 - 3 bed, 2 bath Caribbean Bungalow with Dockage

Holiday Home, Pigeon Key

W15 - 3 bed, 2 bath Caribbean Bungalow with Dockage is a holiday home in Pigeon Key, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

Read more

About W15 - 3 bed, 2 bath Caribbean Bungalow with Dockage

W15 - 3 bed, 2 bath Caribbean Bungalow with Dockage is a holiday home in Pigeon Key, 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 wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,490.

From$356/night

Show›

Best Pet-Friendly Vacation Rentals in Pigeon Key, FL

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

Tropical Private Home w/Hot Tub,BBQ. Bring Your Boat, RV Parking

Holiday Home, Pigeon Key

Tropical Private Home w/Hot Tub,BBQ. Bring Your Boat, RV Parking is a holiday home in Pigeon Key, with pet-friendly space and parking. This stay gives travelers a comfortable base for…

Read more

About Tropical Private Home w/Hot Tub,BBQ. Bring Your Boat, RV Parking

Tropical Private Home w/Hot Tub,BBQ. Bring Your Boat, RV Parking is a holiday home in Pigeon Key, with pet-friendly space 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, hot tub, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,938.

From$277/night

Show›

Welcome to Almost Paradise, a 3 bedroom 2 bath tropical home tucked away onFlamingo Island.

Holiday Home, Pigeon Key

Welcome to Almost Paradise, a 3 bedroom 2 bath tropical home tucked away onFlamingo Island. is a holiday home in Pigeon Key, with pet-friendly space, kitchen access, and room for a group.…

Read more

About Welcome to Almost Paradise, a 3 bedroom 2 bath tropical home tucked away onFlamingo Island.

Welcome to Almost Paradise, a 3 bedroom 2 bath tropical home tucked away onFlamingo Island. is a holiday home in Pigeon Key, with pet-friendly space, 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 wifi, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,174.

From$311/night

Show›

Flamingo House

Holiday Home, Pigeon Key

Flamingo House is a holiday home in Pigeon Key, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

Read more

About Flamingo House

Flamingo House is a holiday home in Pigeon Key, 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 $2,267.

From$324/night

Show›

Waterfront Paradise in Marathon Key – 3BR Home with Private Canal Access!

Holiday Home, Pigeon Key

Waterfront Paradise in Marathon Key – 3BR Home with Private Canal Access! is a holiday home in Pigeon Key, with pet-friendly space, easy beach access, and kitchen access. This stay gives…

Read more

About Waterfront Paradise in Marathon Key – 3BR Home with Private Canal Access!

Waterfront Paradise in Marathon Key – 3BR Home with Private Canal Access! is a holiday home in Pigeon Key, with pet-friendly space, 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: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,462.

From$352/night

Show›

Best Pigeon Key, FL vacation rentals with a kitchen

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

Sombrero Beach Neighborhood - Deep Water Dockage - Spacious 3 Bedroom!

Holiday Home, Pigeon Key

Sombrero Beach Neighborhood - Deep Water Dockage - Spacious 3 Bedroom! is a holiday home in Pigeon Key, with easy beach access, parking, and kitchen access. This stay gives travelers a…

Read more

About Sombrero Beach Neighborhood - Deep Water Dockage - Spacious 3 Bedroom!

Sombrero Beach Neighborhood - Deep Water Dockage - Spacious 3 Bedroom! is a holiday home in Pigeon Key, with easy beach 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: free wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,280.

From$326/night

Show›

W16 - 3 bed, 2 bath Tropical Bungalow with Dockage

Holiday Home, Pigeon Key

W16 - 3 bed, 2 bath Tropical Bungalow with Dockage is a holiday home in Pigeon Key, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

Read more

About W16 - 3 bed, 2 bath Tropical Bungalow with Dockage

W16 - 3 bed, 2 bath Tropical Bungalow with Dockage is a holiday home in Pigeon Key, 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 wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,490.

From$356/night

Show›

Salty Air Retreat. 2 Bedroom 1 Bathroom Half Duplex. Dockside.

Holiday Home, Pigeon Key

Salty Air Retreat. 2 Bedroom 1 Bathroom Half Duplex. Dockside. is a holiday home in Pigeon Key, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable…

Read more

About Salty Air Retreat. 2 Bedroom 1 Bathroom Half Duplex. Dockside.

Salty Air Retreat. 2 Bedroom 1 Bathroom Half Duplex. Dockside. is a holiday home in Pigeon Key, with parking, 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, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,612.

From$373/night

Show›

10-20%off SUMMER weeks-FULLY updated home w/canal to Sombrero-MESSAGE TO INQUIRE

Holiday Home, Pigeon Key

10-20%off SUMMER weeks-FULLY updated home w/canal to Sombrero-MESSAGE TO INQUIRE is a holiday home in Pigeon Key, with parking and kitchen access. This stay gives travelers a comfortable…

Read more

About 10-20%off SUMMER weeks-FULLY updated home w/canal to Sombrero-MESSAGE TO INQUIRE

10-20%off SUMMER weeks-FULLY updated home w/canal to Sombrero-MESSAGE TO INQUIRE is a holiday home in Pigeon Key, 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 wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,651.

From$379/night

Show›

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

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

300/NIGHT~ICE MACHINE~POOL~ CLOSE TO OPEN GULF WATER~FAMILY FRIENDLY HOME,

Holiday Home, Pigeon Key

300/NIGHT~ICE MACHINE~POOL~ CLOSE TO OPEN GULF WATER~FAMILY FRIENDLY HOME, is a holiday home in Pigeon Key, with pool access, easy beach access, and kitchen access. This stay gives…

Read more

About 300/NIGHT~ICE MACHINE~POOL~ CLOSE TO OPEN GULF WATER~FAMILY FRIENDLY HOME,

300/NIGHT~ICE MACHINE~POOL~ CLOSE TO OPEN GULF WATER~FAMILY FRIENDLY HOME, is a holiday home in Pigeon Key, 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, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,362.

From$337/night

Show›

Cottage de la Paz - Charming Keys Retreat Deep Canal, near Dining & Shopping

Holiday Home, Pigeon Key

Cottage de la Paz - Charming Keys Retreat Deep Canal, near Dining & Shopping is a holiday home in Pigeon Key, with parking, kitchen access, and a quieter setting. This stay gives travelers…

Read more

About Cottage de la Paz - Charming Keys Retreat Deep Canal, near Dining & Shopping

Cottage de la Paz - Charming Keys Retreat Deep Canal, near Dining & Shopping is a holiday home in Pigeon Key, with parking, kitchen access, and a quieter setting. 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 free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,635.

From$376/night

Show›

Gulf Open Water, Sunset Views, Protected Boat Dock, Ground Level

Holiday Home, Pigeon Key

Gulf Open Water, Sunset Views, Protected Boat Dock, Ground Level is a holiday home in Pigeon Key, with easy beach access and kitchen access. This stay gives travelers a comfortable base for…

Read more

About Gulf Open Water, Sunset Views, Protected Boat Dock, Ground Level

Gulf Open Water, Sunset Views, Protected Boat Dock, Ground Level is a holiday home in Pigeon Key, with 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: free cancellation, free wifi, kitchen, with kitchen, and kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,682.

From$383/night

Show›

BeachHouse @ Sombrero & Ocean access w/45’ Dock, kayaks and Bikes.

Holiday Home, Pigeon Key

BeachHouse @ Sombrero & Ocean access w/45’ Dock, kayaks and Bikes. is a holiday home in Pigeon Key, with easy beach access, parking, and kitchen access. This stay gives travelers a…

Read more

About BeachHouse @ Sombrero & Ocean access w/45’ Dock, kayaks and Bikes.

BeachHouse @ Sombrero & Ocean access w/45’ Dock, kayaks and Bikes. is a holiday home in Pigeon Key, with easy beach 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: free cancellation, kitchen, with kitchen, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,025.

From$432/night

Show›