Vacation rentals in Rockland Key, FL

112 available vacation rental offers

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Best vacation rentals and Airbnb offers in Rockland Key, FL

KW23 Atlantic Ocean View - Rockland Key, FL

KW23 Atlantic Ocean View

Apartment, Rockland Key

KW23 Atlantic Ocean View is a apartment in Rockland Key, with easy beach access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About KW23 Atlantic Ocean View

KW23 Atlantic Ocean View is a apartment in Rockland Key, with 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, free wifi, accessible, elevator, and internet.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,160.

From$208/night
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INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub! - Rockland Key, FL

INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!

Holiday Home, Rockland Key

INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub! is a holiday home in Rockland Key, with pet-friendly space, easy beach access, and room for a group. This stay gives travelers a…

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About INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!

INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub! is a holiday home in Rockland Key, with pet-friendly space, easy beach 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, hot tub, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,876.

From$268/night
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Casa Atlantica: A studio condo on the Atlantic shore of Key West - Rockland Key, FL

Casa Atlantica: A studio condo on the Atlantic shore of Key West

Condo, Rockland Key

Casa Atlantica: A studio condo on the Atlantic shore of Key West is a condo in Rockland Key, with kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Casa Atlantica: A studio condo on the Atlantic shore of Key West

Casa Atlantica: A studio condo on the Atlantic shore of Key West is a condo in Rockland Key, 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: free wifi, kitchen, with kitchen, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,883.

From$269/night
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Oceanfront Oasis Smathers Beach Condo Sunrise views Island Charm Book today - Rockland Key, FL

Oceanfront Oasis Smathers Beach Condo Sunrise views Island Charm Book today

Condo, Rockland Key

Oceanfront Oasis Smathers Beach Condo Sunrise views Island Charm Book today is a condo in Rockland Key, 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 Rockland 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 $1,914.

From$273/night
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Vacation rentals with a pool in Rockland Key, FL

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

Botanical Island Delight Key West fantastic discounts for Summer & Fall - Rockland Key, FL

Botanical Island Delight Key West fantastic discounts for Summer & Fall

Condo, Rockland Key

Botanical Island Delight Key West fantastic discounts for Summer & Fall is a condo in Rockland Key, with pool access and kitchen access. This stay gives travelers a comfortable base for…

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About Botanical Island Delight Key West fantastic discounts for Summer & Fall

Botanical Island Delight Key West fantastic discounts for Summer & Fall is a condo in Rockland Key, 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: free cancellation, pool, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,196.

From$314/night
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Nautical Adventures in Paradise - Rockland Key, FL

Nautical Adventures in Paradise

Holiday Home, Rockland Key

Nautical Adventures in Paradise is a holiday home in Rockland Key, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Nautical Adventures in Paradise

Nautical Adventures in Paradise is a holiday home in Rockland 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: free cancellation, pool, free wifi, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,948.

From$316/night
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Ocean Hideaway on the Atlantic - Rockland Key, FL

Ocean Hideaway on the Atlantic

Holiday Home, Rockland Key

Ocean Hideaway on the Atlantic is a holiday home in Rockland Key, with pool access and easy beach access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Ocean Hideaway on the Atlantic

Ocean Hideaway on the Atlantic is a holiday home in Rockland 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 $3,044.

From$328/night
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Key West's Best - Rockland Key, FL

Key West's Best

Holiday Home, Rockland Key

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

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About Key West's Best

Key West's Best is a holiday home in Rockland 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 free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,073.

From$332/night
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Vacation rentals with parking in Rockland Key, FL

Find vacation rentals that make arriving by car easier.

Honeymoon Banyan Suite near Higgs Beach - Rockland Key, FL

Honeymoon Banyan Suite near Higgs Beach

Apartment, Rockland Key

Honeymoon Banyan Suite near Higgs Beach is a apartment in Rockland Key, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Honeymoon Banyan Suite near Higgs Beach

Honeymoon Banyan Suite near Higgs Beach is a apartment in Rockland 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 onsite parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,103.

From$300/night
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Honeymoon Palm Suite near Higgs Beach - Rockland Key, FL

Honeymoon Palm Suite near Higgs Beach

Apartment, Rockland Key

Honeymoon Palm Suite near Higgs Beach is a apartment in Rockland Key, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Honeymoon Palm Suite near Higgs Beach

Honeymoon Palm Suite near Higgs Beach is a apartment in Rockland 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 onsite parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,391.

From$342/night
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Starlight Serenity - Hideaway with Stunning Views - Rockland Key, FL

Starlight Serenity - Hideaway with Stunning Views

Holiday Home, Rockland Key

Starlight Serenity - Hideaway with Stunning Views is a holiday home in Rockland Key, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Starlight Serenity - Hideaway with Stunning Views

Starlight Serenity - Hideaway with Stunning Views is a holiday home in Rockland 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,416.

From$345/night
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3 Bedroom 2 Bath Ocean view Condo with Full Kitchen, Covered Parking - Rockland Key, FL

3 Bedroom 2 Bath Ocean view Condo with Full Kitchen, Covered Parking

Condo, Rockland Key

3 Bedroom 2 Bath Ocean view Condo with Full Kitchen, Covered Parking is a condo in Rockland Key, with pool access, easy beach access, and parking. This stay gives travelers a comfortable…

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About 3 Bedroom 2 Bath Ocean view Condo with Full Kitchen, Covered Parking

3 Bedroom 2 Bath Ocean view Condo with Full Kitchen, Covered Parking is a condo in Rockland 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: free cancellation, pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,939.

From$420/night
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Pet-friendly vacation rentals in Rockland Key, FL

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

Cottage with Pool and Boat Dockage just minutes to Key West! - Rockland Key, FL

Cottage with Pool and Boat Dockage just minutes to Key West!

Cottage, Rockland Key

Cottage with Pool and Boat Dockage just minutes to Key West! is a cottage in Rockland Key, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a comfortable…

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About Cottage with Pool and Boat Dockage just minutes to Key West!

Cottage with Pool and Boat Dockage just minutes to Key West! is a cottage in Rockland 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 $1,473.

From$210/night
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Cottage with Pool and Dockage, just minutes to Key West - Rockland Key, FL

Cottage with Pool and Dockage, just minutes to Key West

Cottage, Rockland Key

Cottage with Pool and Dockage, just minutes to Key West is a cottage in Rockland Key, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the…

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About Cottage with Pool and Dockage, just minutes to Key West

Cottage with Pool and Dockage, just minutes to Key West is a cottage in Rockland 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 $1,501.

From$214/night
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Quaint cottage, pool, dockage just minutes to Key West! - Rockland Key, FL

Quaint cottage, pool, dockage just minutes to Key West!

Cottage, Rockland Key

Quaint cottage, pool, dockage just minutes to Key West! is a cottage in Rockland Key, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the…

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About Quaint cottage, pool, dockage just minutes to Key West!

Quaint cottage, pool, dockage just minutes to Key West! is a cottage in Rockland 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 $1,660.

From$237/night
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Our Nautical Home Key West prime location & amenities. Last minute specials. - Rockland Key, FL

Our Nautical Home Key West prime location & amenities. Last minute specials.

Condo, Rockland Key

Our Nautical Home Key West prime location & amenities. Last minute specials. is a condo in Rockland Key, with pool access and kitchen access. This stay gives travelers a comfortable base…

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About Our Nautical Home Key West prime location & amenities. Last minute specials.

Our Nautical Home Key West prime location & amenities. Last minute specials. is a condo in Rockland Key, 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: free cancellation, pool, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,388.

From$341/night
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Vacation rentals with a kitchen in Rockland Key, FL

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

Ocean Hideaway a Key West Nature retreat close to Smathers & 15 to Duval - Rockland Key, FL

Ocean Hideaway a Key West Nature retreat close to Smathers & 15 to Duval

Condo, Rockland Key

Ocean Hideaway a Key West Nature retreat close to Smathers & 15 to Duval is a condo in Rockland Key, with pool access, easy beach access, and kitchen access. This stay gives travelers a…

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About Ocean Hideaway a Key West Nature retreat close to Smathers & 15 to Duval

Ocean Hideaway a Key West Nature retreat close to Smathers & 15 to Duval is a condo in Rockland 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 $2,465.

From$352/night
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Key Wes't Best- Upgraded condo 5 mins to Smathers Beach Fantastic value - Rockland Key, FL

Key Wes't Best- Upgraded condo 5 mins to Smathers Beach Fantastic value

Condo, Rockland Key

Key Wes't Best- Upgraded condo 5 mins to Smathers Beach Fantastic value is a condo in Rockland Key, with pool access, easy beach access, and kitchen access. This stay gives travelers a…

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About Key Wes't Best- Upgraded condo 5 mins to Smathers Beach Fantastic value

Key Wes't Best- Upgraded condo 5 mins to Smathers Beach Fantastic value is a condo in Rockland 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 $2,482.

From$355/night
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Direct Ocean View from Your Condo-No Contact Check-In - Rockland Key, FL

Direct Ocean View from Your Condo-No Contact Check-In

Condo, Rockland Key

Direct Ocean View from Your Condo-No Contact Check-In is a condo in Rockland Key, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for…

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About Direct Ocean View from Your Condo-No Contact Check-In

Direct Ocean View from Your Condo-No Contact Check-In is a condo in Rockland 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 $2,521.

From$360/night
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Blue Moonshine upgrades throughout modern finishes, close to Smathers Beach - Rockland Key, FL

Blue Moonshine upgrades throughout modern finishes, close to Smathers Beach

Condo, Rockland Key

Blue Moonshine upgrades throughout modern finishes, close to Smathers Beach is a condo in Rockland Key, with pool access, easy beach access, and kitchen access. This stay gives travelers a…

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About Blue Moonshine upgrades throughout modern finishes, close to Smathers Beach

Blue Moonshine upgrades throughout modern finishes, close to Smathers Beach is a condo in Rockland 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 $2,615.

From$374/night
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Family-friendly vacation rentals in Rockland Key, FL

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

Sugarloaf Key RV Resort & Cottages - Rockland Key, FL

Sugarloaf Key RV Resort & Cottages

Holiday Home, Rockland Key

Sugarloaf Key RV Resort & Cottages is a holiday home in Rockland Key, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Sugarloaf Key RV Resort & Cottages

Sugarloaf Key RV Resort & Cottages is a holiday home in Rockland 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 $1,210.

From$139/night
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Sugarloaf Key RV Resort & Cottages - Rockland Key, FL

Sugarloaf Key RV Resort & Cottages

Holiday Home, Rockland Key

Sugarloaf Key RV Resort & Cottages is a holiday home in Rockland Key, with pet-friendly space, pool access, and parking. This stay gives travelers a comfortable base for exploring the area,…

Read more

About Sugarloaf Key RV Resort & Cottages

Sugarloaf Key RV Resort & Cottages is a holiday home in Rockland Key, 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, pet friendly, pets friendly, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,199.

From$171/night
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Cottage with swimming pool and dockage, just minutes to Key West! - Rockland Key, FL

Cottage with swimming pool and dockage, just minutes to Key West!

Cottage, Rockland Key

Cottage with swimming pool and dockage, just minutes to Key West! is a cottage in Rockland Key, with pet-friendly space and pool access. This stay gives travelers a comfortable base for…

Read more

About Cottage with swimming pool and dockage, just minutes to Key West!

Cottage with swimming pool and dockage, just minutes to Key West! is a cottage in Rockland 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 $1,394.

From$199/night
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Private Oceanfront Cottage with dockage, pool just minutes to Key West! - Rockland Key, FL

Private Oceanfront Cottage with dockage, pool just minutes to Key West!

Cottage, Rockland Key

Private Oceanfront Cottage with dockage, pool just minutes to Key West! is a cottage in Rockland Key, with pet-friendly space, pool access, and easy beach access. This stay gives travelers…

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About Private Oceanfront Cottage with dockage, pool just minutes to Key West!

Private Oceanfront Cottage with dockage, pool just minutes to Key West! is a cottage in Rockland Key, 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 $1,460.

From$209/night
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