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Holiday homes in Stock Island You’ll Love (Page 8)

Top-Rated Stock Island Holiday homes for Every Budget and Style!

Looking for a holiday home in Stock Island (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 Stock Island.

We found 293 Holiday-homes in Stock Island and the surrounding area (within 20 miles)

Casa Del Sol in Key West, USA

Casa Del Sol

Holiday home in Key West near Stock Island, Florida
Casa Del Sol is a vacation home featuring rooms with free Wifi and air conditioning in the center of Key West.

no reviews

from $66.00 Show details »

Sirens Serenade by Last Key Realty in Key West, USA

Sirens Serenade by Last Key Realty

Holiday home in Key West near Stock Island, Florida , 66 Front Street
Sirens Serenade by Last Key Realty offers accommodations in Key West, a 5-minute walk from Key West Aquarium and 600 yards from Mallory Dock.
  • Parking
  • Swimming pool
  • Swimming Pool

no reviews

from $1.468.33 Show details »

Midtown Mosaic by Last Key Realty in Key West, USA

Midtown Mosaic by Last Key Realty

Holiday home in Key West near Stock Island, Florida , 1322 Thompson Street
Midtown Mosaic by Last Key Realty offers accommodations in Key West, 1.1 miles from Southernmost Point and 1.4 miles from Ernest Hemingway Home and Mu...
  • Parking
  • Pets allowed
  • Swimming pool
  • Swimming Pool

no reviews

from $93.00 Show details »

Treasure Cove in Key West, USA

Treasure Cove

Holiday home in Key West near Stock Island, Florida
Treasure Cove in Key West provides accommodations with free Wifi, a 13-minute walk from Fort Zachary Taylor State Park Beach, one mile from South Beac...
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Fabulous 1 Reviews 9.0

from $93.00 Show details »

Angelfish Reef by Last Key Realty in Key West, USA

Angelfish Reef by Last Key Realty

Holiday home in Key West near Stock Island, Florida , 101 Front Street #8
Angelfish Reef by Last Key Realty is located in Key West, just a 5-minute walk from Key West Aquarium and 600 yards from Mallory Dock.
  • Parking
  • Swimming pool
  • Swimming Pool

no reviews

from $52.00 Show details »

Perfect Harmony by Last Key Realty in Key West, USA

Perfect Harmony by Last Key Realty

Holiday home in Key West near Stock Island, Florida , 1200 Florida Street
Perfect Harmony by Last Key Realty offers accommodations in Key West, a 19-minute walk from Southernmost Point and one mile from Ernest Hemingway Home...
  • Parking
  • Pets allowed
  • Swimming pool
  • Swimming Pool

no reviews

from $75.00 Show details »

Havana House by Last Key Realty in Key West, USA

Havana House by Last Key Realty

Holiday home in Key West near Stock Island, Florida , 915 Grinnell Street
A 14-minute walk from South Beach in Key West, Havana House by Last Key Realty provides accommodations with access to spa facilities.
  • Parking
  • Pets allowed
  • Swimming pool
  • Swimming Pool

no reviews

from $95.00 Show details »

The Royal Compound by Last Key Realty in Key West, USA

The Royal Compound by Last Key Realty

Holiday home in Key West near Stock Island, Florida , 101 Admirals Lane
A 12-minute walk from Fort Zachary Taylor State Park Beach in Key West, The Royal Compound by Last Key Realty features accommodations with access to s...
  • Parking
  • Pets allowed
  • Swimming pool
  • Swimming Pool

no reviews

from $2.009.60 Show details »

Casa Azul-Open Concept Home With Pool in Key West, USA

Casa Azul-Open Concept Home With Pool

Holiday home in Key West near Stock Island, Florida , Elizabeth Street 629
Just a 8-minute walk from Ernest Hemingway Home and Museum and 0.8 miles from Mallory Square, Casa Azul-Open Concept Home With Pool features accommoda...
  • Parking
  • Pets allowed
  • Swimming pool
  • Swimming Pool

no reviews

from $89.00 Show details »

Great Key West Location in Key West, USA

Great Key West Location

Holiday home in Key West near Stock Island, Florida , 100 Admirals Lane
Featuring a private beach area, Great Key West Location provides accommodations in the center of Key West.
  • Parking
  • Pets allowed
  • Family rooms

Superb 5 Reviews 9.4

from $95.00 Show details »

Mangrove Lagoon in Key West, USA

Mangrove Lagoon

Holiday home in Key West near Stock Island, Florida
A comfortable vacation home within the vicinity of Fort Zachary Taylor State Park Beach, Mangrove Lagoon offers a base for a hassle-free getaway in Ke...
  • Parking
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

no reviews

from $414.74 Show details »

Passover Cottage in Key West, USA

Passover Cottage

Holiday home in Key West near Stock Island, Florida
Passover Cottage is located in Key West, just a 9-minute walk from Ernest Hemingway Home and Museum and 0.9 miles from Southernmost Point.
  • Parking
  • Pets allowed
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Very good 8 Reviews 8.4

from $91.00 Show details »

Trumans Hideaway by AvantStay Great Location w Patio Outdoor Dining BBQ Shared Pool Week Long Stays in Key West, USA

Trumans Hideaway by AvantStay Great Loca...

Holiday home in Key West near Stock Island, Florida
Trumans Hideaway by AvantStay Great Location w Patio Outdoor Dining BBQ Shared Pool Week Long Stays is located in Key West, just 1.3 miles from South ...
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Exceptional 1 Reviews 10.0

from $491.98 Show details »

Artist Garden by AvantStay Great Location w Balcony, Outdoor Dining, Shared Pool & BBQ! Week Long Stays in Key West, USA

Artist Garden by AvantStay Great Locatio...

Holiday home in Key West near Stock Island, Florida
Artist Garden by AvantStay Great Location w Balcony, Outdoor Dining, Shared Pool & BBQ!
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

no reviews

from $476.97 Show details »

The Southernmost Comfort House in Key West, USA

The Southernmost Comfort House

Holiday home in Key West near Stock Island, Florida
The Southernmost Comfort House is located in Key West, just a 5-minute walk from Key West Aquarium and 600 yards from Mallory Dock.
  • Parking
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

no reviews

from $2.208.96 Show details »

Boat House by AvantStay Character Cottage Central Location w Shared Pool Month Long Stays in Key West, USA

Boat House by AvantStay Character Cottag...

Holiday home in Key West near Stock Island, Florida
Boat House by AvantStay Character Cottage Central Location w Shared Pool Month Long Stays offers accommodations in Key West, a 10-minute walk from Ern...
  • Parking
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

no reviews

from $92.00 Show details »

Margaret Street Retreat in Key West, USA

Margaret Street Retreat

Holiday home in Key West near Stock Island, Florida
Just a 8-minute walk from Duval Street and 0.6 miles from Ernest Hemingway Home and Museum, Margaret Street Retreat features accommodations in Key Wes...
  • Parking
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

no reviews

from $56.00 Show details »

Paradise Place by AvantStay Key West Old Town Condo w Shared Pool in Key West, USA

Paradise Place by AvantStay Key West Old...

Holiday home in Key West near Stock Island, Florida
Paradise Place by AvantStay Key West Old Town Condo w Shared Pool offers accommodations in Key West, 1.4 miles from Mallory Square and 1.4 miles from ...
  • Pets allowed
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Good 9 Reviews 7.0

from $321.64 Show details »

The Lime and The Coconut by Last Key Realty in Key West, USA

The Lime and The Coconut by Last Key Rea...

Holiday home in Key West near Stock Island, Florida , 421-423 Simonton Street
A 17-minute walk from South Beach in Key West, The Lime and The Coconut by Last Key Realty offers accommodations with access to spa facilities.
  • Pets allowed
  • Swimming pool
  • Swimming Pool

no reviews

from $1.877.36 Show details »

New Hidden Oasis- Waterfall Pool Close to Beach in Key West, USA

New Hidden Oasis- Waterfall Pool Close t...

Holiday home in Key West near Stock Island, Florida , Seidenberg Avenue 2026
New Hidden Oasis- Waterfall Pool Close to Beach offers accommodations in Key West, 1.6 miles from Southernmost Point and 1.8 miles from Ernest Hemingw...
  • Parking
  • Pets allowed
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

no reviews

from $82.00 Show details »

Spirit of Key West by Last Key Realty in Key West, USA

Spirit of Key West by Last Key Realty

Holiday home in Key West near Stock Island, Florida , 1106 Petronia Street
Spirit of Key West by Last Key Realty is located in Key West, just 1.1 miles from Southernmost Point and 1.2 miles from Mallory Square.
  • Parking
  • Swimming pool
  • Swimming Pool

no reviews

from $85.00 Show details »

Flaglers Oasis by AvantStay Private Pool in Key West Month Long Stays Only in Key West, USA

Flaglers Oasis by AvantStay Private Pool...

Holiday home in Key West near Stock Island, Florida
Flaglers Oasis by AvantStay Private Pool in Key West Month Long Stays Only is located in Key West, just 1.6 miles from Southernmost Point and 1.9 mile...
  • Parking
  • Pets allowed
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Exceptional 1 Reviews 10.0

from $71.00 Show details »

The Artists Muse by Last Key Realty in Key West, USA

The Artists Muse by Last Key Realty

Holiday home in Key West near Stock Island, Florida , 712 Love Lane
A 18-minute walk from South Beach in Key West, The Artists Muse by Last Key Realty offers accommodations with access to spa facilities.
  • Swimming pool
  • Swimming Pool

no reviews

from $89.00 Show details »

Casa de Rosalie by AvantStay Great Location w Pool BBQ Outdoor Dining Month Long Stays Only in Key West, USA

Casa de Rosalie by AvantStay Great Locat...

Holiday home in Key West near Stock Island, Florida
Casa de Rosalie by AvantStay Great Location w Pool BBQ Outdoor Dining Month Long Stays Only offers accommodations in Key West, a 19-minute walk from E...
  • Parking
  • Pets allowed
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

no reviews

from $100.00 Show details »

Petronia Cottage in Key West, USA

Petronia Cottage

Holiday home in Key West near Stock Island, Florida
Petronia Cottage offers accommodations in Key West, a 12-minute walk from Duval Street and 0.8 miles from Ernest Hemingway Home and Museum.
  • Parking
  • Pets allowed
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

no reviews

from $56.00 Show details »

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