Holiday homes in Summerland Key You’ll Love (Page 2)

Top-Rated Summerland Key Holiday homes for Every Budget and Style!

Looking for a holiday home in Summerland Key (Florida)? Browse a wide range of vacation rentals – from cozy retreats to spacious family homes – starting at just $63.00 per night. Whether you are planning a weekend getaway or a longer stay, you will find the perfect home away from home in the heart of Summerland Key.

We found 54 Holiday-homes in Summerland Key and the surrounding area (within 20 miles)

Paradise Found

Holiday home in Key West near Summerland Key, Florida

Paradise Found is located in Key West, just 23 miles from Southernmost Point and 23 miles from Mallory Square.

no reviews

from $84.00 Show details »

Blackbeard`s Hideaway

Holiday home in Key West near Summerland Key, Florida

Blackbeard`s Hideaway is located in Key West, just 23 miles from Duval Street and 23 miles from Southernmost Point.

no reviews

from $92.00 Show details »

Tranquility in Paradise - Cudjoe

Holiday home in Summerland Key, Florida , 21069 5th Avenue

Tranquility in Paradise - Cudjoe is located in Summerland Key, just 21 miles from Ernest Hemingway Home and Museum and 21 miles from Duval Street.

Parking
Pets allowed
Family rooms

Exceptional 1 Reviews 10.0

from $87.00 Show details »

Villa of the Setting Sun

Holiday home in Pirates Cove near Summerland Key, Florida

Villa of the Setting Sun offers accommodations in Pirates Cove, 20 miles from Ernest Hemingway Home and Museum and 20 miles from Duval Street.

Parking
Sauna
Outdoor pool
Swimming pool
Swimming Pool

Very good 1 Reviews 8.0

from $2.392.88 Show details »

Key Lime Time

Holiday home in Cudjoe Key near Summerland Key, Florida

Offering pool views, Key Lime Time in Cudjoe Key provides accommodations and a garden.

Parking
Pets allowed
Outdoor pool
Swimming pool
Swimming Pool

no reviews

from $100.00 Show details »

El Paraiso

Holiday home in Summerland Key, Florida

El Paraiso offers accommodations in Summerland Key, 23 miles from Southernmost Point and 23 miles from Mallory Square.

no reviews

from $79.00 Show details »

Tarpon Canal

Holiday home in Key West near Summerland Key, Florida

Tarpon Canal offers accommodations in Key West, 21 miles from Southernmost Point and 21 miles from Mallory Square.

no reviews

from $92.00 Show details »

Keysie Does It by Last Key Realty

Holiday home in Cudjoe Key near Summerland Key, Florida , 21650 Overseas Highway #102

Keysie Does It by Last Key Realty offers accommodations in Cudjoe Key, 21 miles from Ernest Hemingway Home and Museum and 21 miles from Duval Street.

Parking
Swimming pool
Swimming Pool

no reviews

from $411.44 Show details »

Beachside Fantasy

Holiday home in Big Pine Key near Summerland Key, Florida

Beachside Fantasy is located in Big Pine Key, just 23 miles from Florida Keys Aquarium Encounters and 30 miles from Ernest Hemingway Home and Museum.

Parking
Outdoor pool
Swimming pool
Swimming Pool

no reviews

from $91.00 Show details »

Manatee Watch

Holiday home in Big Pine Key near Summerland Key, Florida

Manatee Watch is located in Big Pine Key, just 30 miles from Duval Street and 30 miles from Southernmost Point.

Outdoor pool
Swimming pool
Swimming Pool

no reviews

from $82.00 Show details »

Waterfront Beach House with Dock & Heate...

Holiday home in Summerland Key, Florida , 263 Barry Avenue

Waterfront Beach House with Dock & Heated Pool offers accommodations in Summerland Key, 25 miles from Florida Keys Aquarium Encounters and 28 miles fr...

Parking
Pets allowed
Outdoor pool
Swimming Pool

no reviews

from $85.00 Show details »

Loggerhead Lagoon - Modern Waterfront Ho...

Holiday home in Pirates Cove near Summerland Key, Florida , 886 Loggerhead Lane

Loggerhead Lagoon - Modern Waterfront Home is located in Pirates Cove, just 20 miles from Ernest Hemingway Home and Museum and 20 miles from Duval Str...

Parking
Pets allowed

no reviews

from $53.00 Show details »

Waterfront Cozy Cottage with Boat Ramp &...

Holiday home in Little Torch Key near Summerland Key, Florida , 363 Barry Avenue

Waterfront Cozy Cottage with Boat Ramp & Dock is located in Little Torch Key, just 29 miles from Ernest Hemingway Home and Museum and 29 miles from Du...

Parking
Pets allowed

Very good 1 Reviews 8.0

from $84.00 Show details »

Waterfront Anchor House with Boat Basin...

Holiday home in Summerland Key, Florida , 373 Barry Avenue

Waterfront Anchor House with Boat Basin & Ramp is located in Summerland Key, just 29 miles from Ernest Hemingway Home and Museum and 29 miles from Duv...

Parking
Pets allowed

Exceptional 2 Reviews 9.5

from $87.00 Show details »

Waterfront Haven House with Boat Basin &...

Holiday home in Summerland Key, Florida , 371 Barry Avenue

Waterfront Haven House with Boat Basin & Ramp offers accommodations in Summerland Key, 29 miles from Ernest Hemingway Home and Museum and 29 miles fro...

Parking
Pets allowed

Fabulous 5 Reviews 9.0

from $89.00 Show details »

Waterfront Captain House with Boat Basin...

Holiday home in Summerland Key, Florida , 383 Barry Avenue

Waterfront Captain House with Boat Basin & Ramp offers accommodations in Summerland Key, 29 miles from Ernest Hemingway Home and Museum and 29 miles f...