Vacation rentals in Fiesta Key, FL

Best Vacation rentals and Airbnb offers in Fiesta Key, FL

Newly remodeled, bayfront studio with dock, views & open water access

Holiday Home, Fiesta Key

Newly remodeled, bayfront studio with dock, views & open water access is a holiday home in Fiesta Key, with easy beach access, parking, and kitchen access. This stay gives travelers a…

Read more

About Newly remodeled, bayfront studio with dock, views & open water access

Newly remodeled, bayfront studio with dock, views & open water access is a holiday home in Fiesta 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, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,183.

From$169/night

Show›

Caloosa Cove Resort by CoolVacay

Condo, Fiesta Key

Caloosa Cove Resort by CoolVacay is a condo in Fiesta Key, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

Read more

About Caloosa Cove Resort by CoolVacay

Caloosa Cove Resort by CoolVacay is a condo in Fiesta Key, 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: free cancellation, pool, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,753.

From$320/night

Show›

Gulf View Retreat @ Bay Harbor

Condo, Fiesta Key

Gulf View Retreat @ Bay Harbor is a condo in Fiesta Key, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

Read more

About Gulf View Retreat @ Bay Harbor

Gulf View Retreat @ Bay Harbor is a condo in Fiesta 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, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,256.

From$322/night

Show›

Spectacular Open-Water Sunset Views w/Boat Slip & Trailer Parking. Pet Friendly!

Apartment, Fiesta Key

Spectacular Open-Water Sunset Views w/Boat Slip & Trailer Parking. Pet Friendly! is a apartment in Fiesta Key, with pet-friendly space, parking, and kitchen access. This stay gives…

Read more

About Spectacular Open-Water Sunset Views w/Boat Slip & Trailer Parking. Pet Friendly!

Spectacular Open-Water Sunset Views w/Boat Slip & Trailer Parking. Pet Friendly! is a apartment in Fiesta Key, with pet-friendly space, 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, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,282.

From$326/night

Show›

Browse Vacation Rentals with a Pool in Fiesta Key, FL

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

AQUAMARINE OCEANVIEW+””SPECIAL RATES””+ DOCK+POOL+GYM+SPA+”153”5 STAR REVIEWS!!!

Condo, Fiesta Key

AQUAMARINE OCEANVIEW+””SPECIAL RATES””+ DOCK+POOL+GYM+SPA+”153”5 STAR REVIEWS!!! is a condo in Fiesta Key, with pool access and easy beach access. This stay gives travelers a comfortable…

Read more

About AQUAMARINE OCEANVIEW+””SPECIAL RATES””+ DOCK+POOL+GYM+SPA+”153”5 STAR REVIEWS!!!

AQUAMARINE OCEANVIEW+””SPECIAL RATES””+ DOCK+POOL+GYM+SPA+”153”5 STAR REVIEWS!!! is a condo in Fiesta Key, with pool access and easy beach 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 $2,440.

From$349/night

Show›

Islamorada Bay Harbour 2/2.5 Condo Free DOCK included MONTHLY DISCOUNTS!

Condo, Fiesta Key

Islamorada Bay Harbour 2/2.5 Condo Free DOCK included MONTHLY DISCOUNTS! is a condo in Fiesta Key, with pool access, easy beach access, and kitchen access. This stay gives travelers a…

Read more

About Islamorada Bay Harbour 2/2.5 Condo Free DOCK included MONTHLY DISCOUNTS!

Islamorada Bay Harbour 2/2.5 Condo Free DOCK included MONTHLY DISCOUNTS! is a condo in Fiesta 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: free cancellation, pool, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,695.

From$385/night

Show›

Second Floor Den Suite – Sunny Islamorada Escape, Pool, Beach, Marina, Sleeps 6

Apartment, Fiesta Key

Second Floor Den Suite – Sunny Islamorada Escape, Pool, Beach, Marina, Sleeps 6 is a apartment in Fiesta Key, with pool access, easy beach access, and kitchen access. This stay gives…

Read more

About Second Floor Den Suite – Sunny Islamorada Escape, Pool, Beach, Marina, Sleeps 6

Second Floor Den Suite – Sunny Islamorada Escape, Pool, Beach, Marina, Sleeps 6 is a apartment in Fiesta 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 $2,924.

From$418/night

Show›

Spectacular Views of Ocean with Pool and Boat Slip.

Holiday Home, Fiesta Key

Spectacular Views of Ocean with Pool and Boat Slip. is a holiday home in Fiesta Key, with pool access and easy beach access. This stay gives travelers a comfortable base for exploring the…

Read more

About Spectacular Views of Ocean with Pool and Boat Slip.

Spectacular Views of Ocean with Pool and Boat Slip. is a holiday home in Fiesta Key, with pool access and easy beach 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, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,160.

From$451/night

Show›

Best Fiesta Key, FL vacation rentals with parking

Find vacation rentals that make arriving by car easier.

Waterfront & snowbird-friendly studio with dock & quick open water access

Apartment, Fiesta Key

Waterfront & snowbird-friendly studio with dock & quick open water access is a apartment in Fiesta Key, with easy beach access, parking, and kitchen access. This stay gives travelers a…

Read more

About Waterfront & snowbird-friendly studio with dock & quick open water access

Waterfront & snowbird-friendly studio with dock & quick open water access is a apartment in Fiesta 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, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,190.

From$170/night

Show›

Tropical oasis near all the action with central AC & balcony

Condo, Fiesta Key

Tropical oasis near all the action with central AC & balcony is a condo in Fiesta Key, with outdoor space, parking, and kitchen access. This stay gives travelers a comfortable base for…

Read more

About Tropical oasis near all the action with central AC & balcony

Tropical oasis near all the action with central AC & balcony is a condo in Fiesta Key, with outdoor space, 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 $1,698.

From$243/night

Show›

Enchanting waterfront townhouse with balcony, mini oasis pool, & washer/dryer

Holiday Home, Fiesta Key

Enchanting waterfront townhouse with balcony, mini oasis pool, & washer/dryer is a holiday home in Fiesta Key, with pool access, easy beach access, and outdoor space. This stay gives…

Read more

About Enchanting waterfront townhouse with balcony, mini oasis pool, & washer/dryer

Enchanting waterfront townhouse with balcony, mini oasis pool, & washer/dryer is a holiday home in Fiesta Key, 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, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,819.

From$260/night

Show›

Experience coastal bliss at Oceanside Isle, a spacious 3-bedroom condo in Long Key.

Condo, Fiesta Key

Experience coastal bliss at Oceanside Isle, a spacious 3-bedroom condo in Long Key. is a condo in Fiesta Key, with easy beach access, parking, and kitchen access. This stay gives travelers…

Read more

About Experience coastal bliss at Oceanside Isle, a spacious 3-bedroom condo in Long Key.

Experience coastal bliss at Oceanside Isle, a spacious 3-bedroom condo in Long Key. is a condo in Fiesta 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 $3,381.

From$483/night

Show›

Best Pet-Friendly Vacation Rentals in Fiesta Key, FL

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

2/2 Duplex, Pool, Tiki Hut, Duck Key, Clean Clear Canal

Holiday Home, Fiesta Key

2/2 Duplex, Pool, Tiki Hut, Duck Key, Clean Clear Canal is a holiday home in Fiesta Key, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a comfortable…

Read more

About 2/2 Duplex, Pool, Tiki Hut, Duck Key, Clean Clear Canal

2/2 Duplex, Pool, Tiki Hut, Duck Key, Clean Clear Canal is a holiday home in Fiesta 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: free cancellation, pool, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,829.

From$261/night

Show›

Coastal Waterfront Home with Amazing Views and Great Location

Holiday Home, Fiesta Key

Coastal Waterfront Home with Amazing Views and Great Location is a holiday home in Fiesta Key, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable…

Read more

About Coastal Waterfront Home with Amazing Views and Great Location

Coastal Waterfront Home with Amazing Views and Great Location is a holiday home in Fiesta 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, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,917.

From$274/night

Show›

2/2 Duplex, Pool,Tiki Hut, Duck Key Clean wide Canal

Holiday Home, Fiesta Key

2/2 Duplex, Pool,Tiki Hut, Duck Key Clean wide Canal is a holiday home in Fiesta Key, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a comfortable base…

Read more

About 2/2 Duplex, Pool,Tiki Hut, Duck Key Clean wide Canal

2/2 Duplex, Pool,Tiki Hut, Duck Key Clean wide Canal is a holiday home in Fiesta 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: free cancellation, pool, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,039.

From$291/night

Show›

PLUNGE POOL VILLA ON BLUE WATER LAGOON DUCK Key/MARATHON, FL

Villa, Fiesta Key

PLUNGE POOL VILLA ON BLUE WATER LAGOON DUCK Key/MARATHON, FL is a villa in Fiesta Key, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring…

Read more

About PLUNGE POOL VILLA ON BLUE WATER LAGOON DUCK Key/MARATHON, FL

PLUNGE POOL VILLA ON BLUE WATER LAGOON DUCK Key/MARATHON, FL is a villa in Fiesta Key, 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 $2,317.

From$331/night

Show›

Best Fiesta Key, FL vacation rentals with a kitchen

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

ConchKeyLanding https://www.conchkeylandingflkeys.com/

Apartment, Fiesta Key

ConchKeyLanding https://www.conchkeylandingflkeys.com/ is a apartment in Fiesta Key, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

Read more

About ConchKeyLanding https://www.conchkeylandingflkeys.com/

ConchKeyLanding https://www.conchkeylandingflkeys.com/ is a apartment in Fiesta 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, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,161.

From$309/night

Show›

Deep water docking with quick ocean or open water access

Holiday Home, Fiesta Key

Deep water docking with quick ocean or open water access is a holiday home in Fiesta Key, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base…

Read more

About Deep water docking with quick ocean or open water access

Deep water docking with quick ocean or open water access is a holiday home in Fiesta 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, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,244.

From$321/night

Show›

Keys Comfort: 1BR Condo with Den, Kitchen & Beach Access

Condo, Fiesta Key

Keys Comfort: 1BR Condo with Den, Kitchen & Beach Access is a condo in Fiesta Key, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for…

Read more

About Keys Comfort: 1BR Condo with Den, Kitchen & Beach Access

Keys Comfort: 1BR Condo with Den, Kitchen & Beach Access is a condo in Fiesta 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 $2,971.

From$424/night

Show›

Stay Salty: Keys Dreams 1BR Condo Steps from the Sand

Condo, Fiesta Key

Stay Salty: Keys Dreams 1BR Condo Steps from the Sand is a condo in Fiesta Key, with pool access, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

Read more

About Stay Salty: Keys Dreams 1BR Condo Steps from the Sand

Stay Salty: Keys Dreams 1BR Condo Steps from the Sand is a condo in Fiesta Key, 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: pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,971.

From$424/night

Show›

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

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

Key Lime Cottage: A Stunning Duck Key Retreat with Private Dip Pool and Scenic Water Views!

Guest House, Fiesta Key

Key Lime Cottage: A Stunning Duck Key Retreat with Private Dip Pool and Scenic Water Views! is a guest house in Fiesta Key, with pool access, parking, and kitchen access. This stay gives…

Read more

About Key Lime Cottage: A Stunning Duck Key Retreat with Private Dip Pool and Scenic Water Views!

Key Lime Cottage: A Stunning Duck Key Retreat with Private Dip Pool and Scenic Water Views! is a guest house in Fiesta Key, 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 $1,953.

From$279/night

Show›

Conch Key Cottage 2 bed 1 bath home w/ramp access

Holiday Home, Fiesta Key

Conch Key Cottage 2 bed 1 bath home w/ramp access is a holiday home in Fiesta Key, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the…

Read more

About Conch Key Cottage 2 bed 1 bath home w/ramp access

Conch Key Cottage 2 bed 1 bath home w/ramp access is a holiday home in Fiesta 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: hot tub, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,062.

From$295/night

Show›

New - Oceanfront Estate - Private Beach - Heated Pool - Stunning

Holiday Home, Fiesta Key

New - Oceanfront Estate - Private Beach - Heated Pool - Stunning is a holiday home in Fiesta Key, with pool access, easy beach access, and kitchen access. This stay gives travelers a…

Read more

About New - Oceanfront Estate - Private Beach - Heated Pool - Stunning

New - Oceanfront Estate - Private Beach - Heated Pool - Stunning is a holiday home in Fiesta 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, kitchen, with kitchen, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $9,070.

From$1,296/night

Show›

Oceanfront Cottage With Stunning Pool & Dockage in Islamorada

Cottage, Fiesta Key

Oceanfront Cottage With Stunning Pool & Dockage in Islamorada is a cottage in Fiesta Key, with pool access and easy beach access. This stay gives travelers a comfortable base for exploring…

Read more

About Oceanfront Cottage With Stunning Pool & Dockage in Islamorada

Oceanfront Cottage With Stunning Pool & Dockage in Islamorada is a cottage in Fiesta Key, with pool access and easy beach 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, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $11,334.

From$1,619/night

Show›