Vacation rentals in Matecumbe Keys, FL

Best Vacation rentals and Airbnb offers in Matecumbe Keys, FL

Caloosa Cove Resort by CoolVacay

Condo, Matecumbe Keys

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

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About Caloosa Cove Resort by CoolVacay

Caloosa Cove Resort by CoolVacay is a condo in Matecumbe Keys, 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

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Gulf View Retreat @ Bay Harbor

Condo, Matecumbe Keys

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

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About Gulf View Retreat @ Bay Harbor

Gulf View Retreat @ Bay Harbor is a condo in Matecumbe Keys, 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 $2,251.

From$322/night

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

Condo, Matecumbe Keys

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

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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 Matecumbe Keys, 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

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Coastal Studio Getaway – Second Floor with Partial Water Views

Apartment, Matecumbe Keys

Coastal Studio Getaway – Second Floor with Partial Water Views is a apartment in Matecumbe Keys, with pool access and kitchen access. This stay gives travelers a comfortable base for…

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About Coastal Studio Getaway – Second Floor with Partial Water Views

Coastal Studio Getaway – Second Floor with Partial Water Views is a apartment in Matecumbe Keys, 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, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,440.

From$349/night

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Browse Vacation Rentals with a Pool in Matecumbe Keys, FL

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

Steps to Windley Key! 3 Pet-friendly Units w/ Balcony! Beach Access & Pool

Apartment, Matecumbe Keys

Steps to Windley Key! 3 Pet-friendly Units w/ Balcony! Beach Access & Pool is a apartment in Matecumbe Keys, with pet-friendly space, pool access, and easy beach access. This stay gives…

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About Steps to Windley Key! 3 Pet-friendly Units w/ Balcony! Beach Access & Pool

Steps to Windley Key! 3 Pet-friendly Units w/ Balcony! Beach Access & Pool is a apartment in Matecumbe Keys, with pet-friendly space, 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, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,718.

From$245/night

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Exquisite Unit w/ Balcony and Kitchenette! Pool Pets Allowed, Bike Rental!

Apartment, Matecumbe Keys

Exquisite Unit w/ Balcony and Kitchenette! Pool Pets Allowed, Bike Rental! is a apartment in Matecumbe Keys, with pet-friendly space, pool access, and outdoor space. This stay gives…

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About Exquisite Unit w/ Balcony and Kitchenette! Pool Pets Allowed, Bike Rental!

Exquisite Unit w/ Balcony and Kitchenette! Pool Pets Allowed, Bike Rental! is a apartment in Matecumbe Keys, 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: free cancellation, pool, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,774.

From$253/night

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

Condo, Matecumbe Keys

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

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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 Matecumbe Keys, 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

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Beautiful 'Keysey' Condo in Bay Harbour Gated Community 26-0169

Condo, Matecumbe Keys

Beautiful 'Keysey' Condo in Bay Harbour Gated Community 26-0169 is a condo in Matecumbe Keys, with pool access and easy beach access. This stay gives travelers a comfortable base for…

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About Beautiful 'Keysey' Condo in Bay Harbour Gated Community 26-0169

Beautiful 'Keysey' Condo in Bay Harbour Gated Community 26-0169 is a condo in Matecumbe Keys, 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 $2,780.

From$397/night

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Best Matecumbe Keys, FL vacation rentals with parking

Find vacation rentals that make arriving by car easier.

Snorkel and Kayak in Islamorada! Unit w/ Balcony! Pets Allowed, FREE Parking

Apartment, Matecumbe Keys

Snorkel and Kayak in Islamorada! Unit w/ Balcony! Pets Allowed, FREE Parking is a apartment in Matecumbe Keys, with pet-friendly space, pool access, and outdoor space. This stay gives…

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About Snorkel and Kayak in Islamorada! Unit w/ Balcony! Pets Allowed, FREE Parking

Snorkel and Kayak in Islamorada! Unit w/ Balcony! Pets Allowed, FREE Parking is a apartment in Matecumbe Keys, 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: free cancellation, pool, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,859.

From$266/night

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Comfort and Convenience! Free Onsite Parking, Pets Allowed, Free Breakfast

Apartment, Matecumbe Keys

Comfort and Convenience! Free Onsite Parking, Pets Allowed, Free Breakfast is a apartment in Matecumbe Keys, with pet-friendly space, pool access, and parking. This stay gives travelers a…

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About Comfort and Convenience! Free Onsite Parking, Pets Allowed, Free Breakfast

Comfort and Convenience! Free Onsite Parking, Pets Allowed, Free Breakfast is a apartment in Matecumbe Keys, with pet-friendly space, 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, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,955.

From$279/night

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Prime Location! Pet-Friendly Property, Free Parking, Free Breakfast

Apartment, Matecumbe Keys

Prime Location! Pet-Friendly Property, Free Parking, Free Breakfast is a apartment in Matecumbe Keys, with pet-friendly space, pool access, and parking. This stay gives travelers a…

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About Prime Location! Pet-Friendly Property, Free Parking, Free Breakfast

Prime Location! Pet-Friendly Property, Free Parking, Free Breakfast is a apartment in Matecumbe Keys, with pet-friendly space, 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, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,955.

From$279/night

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Your Home Away From Home! Onsite Pool, Free Breakfast, Free Parking

Apartment, Matecumbe Keys

Your Home Away From Home! Onsite Pool, Free Breakfast, Free Parking is a apartment in Matecumbe Keys, with pet-friendly space, pool access, and parking. This stay gives travelers a…

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About Your Home Away From Home! Onsite Pool, Free Breakfast, Free Parking

Your Home Away From Home! Onsite Pool, Free Breakfast, Free Parking is a apartment in Matecumbe Keys, with pet-friendly space, 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, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,955.

From$279/night

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Best Pet-Friendly Vacation Rentals in Matecumbe Keys, FL

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

Discover Florida Keys! Seaside Villa w/ Patio! Marina, Pool, Parking, Breakfast

Apartment, Matecumbe Keys

Discover Florida Keys! Seaside Villa w/ Patio! Marina, Pool, Parking, Breakfast is a apartment in Matecumbe Keys, with pet-friendly space, pool access, and outdoor space. This stay gives…

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About Discover Florida Keys! Seaside Villa w/ Patio! Marina, Pool, Parking, Breakfast

Discover Florida Keys! Seaside Villa w/ Patio! Marina, Pool, Parking, Breakfast is a apartment in Matecumbe Keys, 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: free cancellation, pool, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,677.

From$240/night

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Sportfishing in Florida Keys! FREE Parking, Pets Allowed, Pool, Bike Rentals!

Apartment, Matecumbe Keys

Sportfishing in Florida Keys! FREE Parking, Pets Allowed, Pool, Bike Rentals! is a apartment in Matecumbe Keys, with pet-friendly space, pool access, and parking. This stay gives travelers…

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About Sportfishing in Florida Keys! FREE Parking, Pets Allowed, Pool, Bike Rentals!

Sportfishing in Florida Keys! FREE Parking, Pets Allowed, Pool, Bike Rentals! is a apartment in Matecumbe Keys, with pet-friendly space, 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, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,677.

From$240/night

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Kayak in Florida Keys! Seaside Villa w/ Patio! Marina, Pool, Kayak

Apartment, Matecumbe Keys

Kayak in Florida Keys! Seaside Villa w/ Patio! Marina, Pool, Kayak is a apartment in Matecumbe Keys, with pet-friendly space, pool access, and outdoor space. This stay gives travelers a…

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About Kayak in Florida Keys! Seaside Villa w/ Patio! Marina, Pool, Kayak

Kayak in Florida Keys! Seaside Villa w/ Patio! Marina, Pool, Kayak is a apartment in Matecumbe Keys, 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: free cancellation, pool, free wifi, pet friendly, and pets friendly.

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

From$242/night

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Seaside Villas w/ Ocean Views & Front Porch! Marina, Pets Allowed, Bike Rental

Apartment, Matecumbe Keys

Seaside Villas w/ Ocean Views & Front Porch! Marina, Pets Allowed, Bike Rental is a apartment in Matecumbe Keys, with pet-friendly space, pool access, and easy beach access. This stay gives…

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About Seaside Villas w/ Ocean Views & Front Porch! Marina, Pets Allowed, Bike Rental

Seaside Villas w/ Ocean Views & Front Porch! Marina, Pets Allowed, Bike Rental is a apartment in Matecumbe Keys, with pet-friendly space, 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, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,718.

From$245/night

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Best Matecumbe Keys, FL vacation rentals with a kitchen

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

Spacious Unit w/ Kitchenette & Balcony! Marina, Pets Allowed, Free Breakfast

Apartment, Matecumbe Keys

Spacious Unit w/ Kitchenette & Balcony! Marina, Pets Allowed, Free Breakfast is a apartment in Matecumbe Keys, with pet-friendly space, pool access, and outdoor space. This stay gives…

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About Spacious Unit w/ Kitchenette & Balcony! Marina, Pets Allowed, Free Breakfast

Spacious Unit w/ Kitchenette & Balcony! Marina, Pets Allowed, Free Breakfast is a apartment in Matecumbe Keys, 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: free cancellation, pool, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,101.

From$300/night

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Spacious Unit w/ Kitchenette & Balcony! Marina, Pets Allowed, Free Breakfast

Apartment, Matecumbe Keys

Spacious Unit w/ Kitchenette & Balcony! Marina, Pets Allowed, Free Breakfast is a apartment in Matecumbe Keys, with pet-friendly space, pool access, and outdoor space. This stay gives…

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About Spacious Unit w/ Kitchenette & Balcony! Marina, Pets Allowed, Free Breakfast

Spacious Unit w/ Kitchenette & Balcony! Marina, Pets Allowed, Free Breakfast is a apartment in Matecumbe Keys, 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: free cancellation, pool, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,172.

From$310/night

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PRIME LOCATION Islamorada Anglers Reef Oceanview Private Beaches, Pool & Marina

Holiday Home, Matecumbe Keys

PRIME LOCATION Islamorada Anglers Reef Oceanview Private Beaches, Pool & Marina is a holiday home in Matecumbe Keys, with pool access, easy beach access, and parking. This stay gives…

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About PRIME LOCATION Islamorada Anglers Reef Oceanview Private Beaches, Pool & Marina

PRIME LOCATION Islamorada Anglers Reef Oceanview Private Beaches, Pool & Marina is a holiday home in Matecumbe Keys, 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: free cancellation, pool, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,413.

From$345/night

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Islamorada Luxury Waterfront Condo with Boat Slip

Condo, Matecumbe Keys

Islamorada Luxury Waterfront Condo with Boat Slip is a condo in Matecumbe Keys, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for…

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About Islamorada Luxury Waterfront Condo with Boat Slip

Islamorada Luxury Waterfront Condo with Boat Slip is a condo in Matecumbe Keys, 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 $2,798.

From$400/night

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Our Favorite Family-Friendly Vacation Rentals in Matecumbe Keys, FL

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

Cozy 1-bedroom Kemp Cottage in peaceful Islamorada, perfect for a romantic getaway.

Apartment, Matecumbe Keys

Cozy 1-bedroom Kemp Cottage in peaceful Islamorada, perfect for a romantic getaway. is a apartment in Matecumbe Keys, with parking, kitchen access, and room for a group. This stay gives…

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About Cozy 1-bedroom Kemp Cottage in peaceful Islamorada, perfect for a romantic getaway.

Cozy 1-bedroom Kemp Cottage in peaceful Islamorada, perfect for a romantic getaway. is a apartment in Matecumbe Keys, 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 wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,065.

From$295/night

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Family Escape in Islamorada! Seaside Unit w/ Balcony! Water Sports Equipment

Apartment, Matecumbe Keys

Family Escape in Islamorada! Seaside Unit w/ Balcony! Water Sports Equipment is a apartment in Matecumbe Keys, with pet-friendly space, pool access, and outdoor space. This stay gives…

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About Family Escape in Islamorada! Seaside Unit w/ Balcony! Water Sports Equipment

Family Escape in Islamorada! Seaside Unit w/ Balcony! Water Sports Equipment is a apartment in Matecumbe Keys, 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: free cancellation, pool, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,217.

From$317/night

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Renovated Anglers Reef 2BR + Sleeper + Ocean Views, Pool, Marina, Sleeps 8

Holiday Home, Matecumbe Keys

Renovated Anglers Reef 2BR + Sleeper + Ocean Views, Pool, Marina, Sleeps 8 is a holiday home in Matecumbe Keys, with pool access, easy beach access, and kitchen access. This stay gives…

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About Renovated Anglers Reef 2BR + Sleeper + Ocean Views, Pool, Marina, Sleeps 8

Renovated Anglers Reef 2BR + Sleeper + Ocean Views, Pool, Marina, Sleeps 8 is a holiday home in Matecumbe Keys, 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, kitchen, with kitchen, and kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,442.

From$349/night

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Discover comfort at Alligator Reef - Lobster Home in Islamorada, perfect for families.

Holiday Home, Matecumbe Keys

Discover comfort at Alligator Reef - Lobster Home in Islamorada, perfect for families. is a holiday home in Matecumbe Keys, with pet-friendly space and kitchen access. This stay gives…

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About Discover comfort at Alligator Reef - Lobster Home in Islamorada, perfect for families.

Discover comfort at Alligator Reef - Lobster Home in Islamorada, perfect for families. is a holiday home in Matecumbe Keys, 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 $2,781.

From$397/night

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