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Holiday homes in Stock Island You’ll Love (Page 9)

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)

Soul of the South by Last Key Realty in Key West, USA

Soul of the South by Last Key Realty

Holiday home in Key West near Stock Island, Florida , 623 Grinnell Street
Soul of the South by Last Key Realty offers accommodations in Key West, a 13-minute walk from Ernest Hemingway Home and Museum and one mile from Mallo...
  • Swimming pool
  • Swimming Pool

no reviews

from $89.00 Show details »

The Fleming Suite in Key West, USA

The Fleming Suite

Holiday home in Key West near Stock Island, Florida
The Fleming Suite offers accommodations in Key West, a 18-minute walk from Duval Street and 1.2 miles from Southernmost Point.
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Pleasant 3 Reviews 6.7

from $239.36 Show details »

The Caroline Suite in Key West, USA

The Caroline Suite

Holiday home in Key West near Stock Island, Florida
The Caroline Suite offers accommodations in Key West, 1.2 miles from Southernmost Point and 1.6 miles from Mallory Square.
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

no reviews

from $274.80 Show details »

The Elizabeth Suite in Key West, USA

The Elizabeth Suite

Holiday home in Key West near Stock Island, Florida
The Elizabeth Suite offers accommodations in Key West, 1.2 miles from Southernmost Point and 1.6 miles from Mallory Square.
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Good 1 Reviews 7.0

from $308.63 Show details »

Angelas Eclectic Gallery by Last Key Realty in Key West, USA

Angelas Eclectic Gallery by Last Key Rea...

Holiday home in Key West near Stock Island, Florida , 1017 Angela Street
Angelas Eclectic Gallery by Last Key Realty is located in Key West, just a 14-minute walk from Ernest Hemingway Home and Museum and 1.1 miles from Mal...
  • Parking
  • Pets allowed
  • Swimming pool
  • Swimming Pool

no reviews

from $55.00 Show details »

New The Cottage at James House in Key West, USA

New The Cottage at James House

Holiday home in Key West near Stock Island, Florida , 512 Caroline Street
New The Cottage at James House is located in Key West, just a 5-minute walk from Key West Aquarium and 500 yards from Mallory Dock.
  • Pets allowed
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Fabulous 8 Reviews 8.6

from $319.97 Show details »

Curry House - Pool, King Bed & Balcony! Room 7 in Key West, USA

Curry House - Pool, King Bed & Balcony!...

Holiday home in Key West near Stock Island, Florida , Fleming Street 806
Curry House - Pool, King Bed & Balcony!
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Good 2 Reviews 7.5

from $164.14 Show details »

Curry House - Room 9 in Key West, USA

Curry House - Room 9

Holiday home in Key West near Stock Island, Florida , Fleming Street 806
Curry House - Room 9 is located in Key West, just a 14-minute walk from Mallory Square and 0.7 miles from Key West Aquarium.
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Okay 5 Reviews 5.6

from $166.93 Show details »

Curry House - Room 5 in Key West, USA

Curry House - Room 5

Holiday home in Key West near Stock Island, Florida , Fleming Street 806
Curry House - Room 5 is located in Key West, just a 14-minute walk from Mallory Square and 0.7 miles from Key West Aquarium.
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Very good 3 Reviews 8.3

from $186.34 Show details »

Curry House- 3rd Floor, King Bed, & Balcony Room 8 in Key West, USA

Curry House- 3rd Floor, King Bed, & Balc...

Holiday home in Key West near Stock Island, Florida , Fleming Street 806
Curry House- 3rd Floor, King Bed, & Balcony Room 8 offers accommodations in Key West, a 14-minute walk from Mallory Square and 0.7 miles from Key West...
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Good 9 Reviews 7.4

from $195.39 Show details »

Curry House - Rooms 3 & 4 in Key West, USA

Curry House - Rooms 3 & 4

Holiday home in Key West near Stock Island, Florida , Fleming Street 806
Curry House - Rooms 3 & 4 offers accommodations in Key West, a 14-minute walk from Mallory Square and 0.7 miles from Key West Aquarium.
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Pleasant 2 Reviews 6.0

from $268.35 Show details »

Modern in the Meadows by Last Key Realty in Key West, USA

Modern in the Meadows by Last Key Realty

Holiday home in Key West near Stock Island, Florida , 1312 Pine Street
Modern in the Meadows by Last Key Realty offers accommodations in Key West, 1.3 miles from Southernmost Point and 1.4 miles from Mallory Square.
  • Parking
  • Pets allowed
  • Swimming pool
  • Swimming Pool

no reviews

from $51.00 Show details »

*New Listing* Cozy Key West Hideaway in Old Town with a pool in Key West, USA

*New Listing* Cozy Key West Hideaway in...

Holiday home in Key West near Stock Island, Florida , 611 Grinnell Street Unit 4
Just 1.1 miles from Higgs Beach and 1.1 miles from South Beach, *New Listing* Cozy Key West Hideaway in Old Town with a pool features accommodations i...
  • Pets allowed
  • Family rooms
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

no reviews

from $76.00 Show details »

Casa Avila by Last Key Realty in Key West, USA

Casa Avila by Last Key Realty

Holiday home in Key West near Stock Island, Florida , 625 Eaton Street
Casa Avila by Last Key Realty offers accommodations in Key West, a 11-minute walk from Mallory Square and 0.6 miles from Key West Aquarium.
  • Parking
  • Swimming pool
  • Swimming Pool

no reviews

from $70.00 Show details »

Land Of Love by AvantStay Pets Allowed Shared Pool Great Location Month Long Stays Only in Key West, USA

Land Of Love by AvantStay Pets Allowed S...

Holiday home in Key West near Stock Island, Florida
Land Of Love by AvantStay Pets Allowed Shared Pool Great Location Month Long Stays Only is located in Key West, just a 16-minute walk from Ernest Hemi...
  • Parking
  • Pets allowed
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

no reviews

from $56.00 Show details »

Margarets Magic Compound by Last Key Realty in Key West, USA

Margarets Magic Compound by Last Key Rea...

Holiday home in Key West near Stock Island, Florida , 515-517 Margaret Street
Margarets Magic Compound by Last Key Realty is located in Key West, just a 13-minute walk from Ernest Hemingway Home and Museum and 0.8 miles from Mal...
  • Pets allowed
  • Swimming pool
  • Swimming Pool

no reviews

from $61.00 Show details »

Abaco - Large waterfront 2x2 end unit with boat slip in Key West, USA

Abaco - Large waterfront 2x2 end unit wi...

Holiday home in Key West near Stock Island, Florida , 915 Eisenhower Drive
Just a 16-minute walk from Rest Beach and 1.1 miles from South Beach, Abaco - Large waterfront 2x2 end unit with boat slip features accommodations in ...
  • Parking
  • Pets allowed
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Fabulous 5 Reviews 8.8

from $334.88 Show details »

Curacao - Large 2x2 Waterfront Condo Great View Pool & Dock in Key West, USA

Curacao - Large 2x2 Waterfront Condo Gre...

Holiday home in Key West near Stock Island, Florida , 915 Eisenhower Drive
Curacao - Large 2x2 Waterfront Condo Great View Pool & Dock offers accommodations in Key West, 1.1 miles from Ernest Hemingway Home and Museum and 1.1...
  • Parking
  • Pets allowed
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Superb 11 Reviews 9.4

from $334.88 Show details »

Spacious Updated Waterfront Condo 2x2 Pool Dock in Key West, USA

Spacious Updated Waterfront Condo 2x2 Po...

Holiday home in Key West near Stock Island, Florida , 915 Eisenhower Drive
Just a 16-minute walk from Rest Beach and 1.1 miles from South Beach, Spacious Updated Waterfront Condo 2x2 Pool Dock features accommodations in Key W...
  • Parking
  • Pets allowed
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Fabulous 2 Reviews 9.0

from $334.88 Show details »

Aruba - Downtown Waterfront 2x2 Dock & Pool Pet-Friendly in Key West, USA

Aruba - Downtown Waterfront 2x2 Dock & P...

Holiday home in Key West near Stock Island, Florida , 915 Eisenhower Drive
Just 1.1 miles from Ernest Hemingway Home and Museum and 1.1 miles from Duval Street, Aruba - Downtown Waterfront 2x2 Dock & Pool Pet-Friendly feature...
  • Parking
  • Pets allowed
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Exceptional 15 Reviews 9.8

from $425.09 Show details »

Downtown Waterfront Penthouse Pool Parking Dock in Key West, USA

Downtown Waterfront Penthouse Pool Parki...

Holiday home in Key West near Stock Island, Florida , 915 Eisenhower Drive
Downtown Waterfront Penthouse Pool Parking Dock is located in Key West, just 1.1 miles from Ernest Hemingway Home and Museum and 1.1 miles from Duval ...
  • Parking
  • Pets allowed
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Superb 3 Reviews 9.3

from $1.210.17 Show details »

Waterfront Penthouse sleeps 16 w Pool & Boat Dock in Key West, USA

Waterfront Penthouse sleeps 16 w Pool &...

Holiday home in Key West near Stock Island, Florida , 915 Eisenhower Drive
Waterfront Penthouse sleeps 16 w Pool & Boat Dock is located in Key West, just 1.1 miles from Ernest Hemingway Home and Museum and 1.1 miles from Duva...
  • Parking
  • Pets allowed
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Fabulous 12 Reviews 8.9

from $1.210.17 Show details »

Downtown 4x4 Waterfront Penthouse Pool Dock Pet in Key West, USA

Downtown 4x4 Waterfront Penthouse Pool D...

Holiday home in Key West near Stock Island, Florida , 915 Eisenhower Drive
Downtown 4x4 Waterfront Penthouse Pool Dock Pet is located in Key West, just 1.1 miles from Ernest Hemingway Home and Museum and 1.1 miles from Duval ...
  • Parking
  • Pets allowed
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Superb 9 Reviews 9.2

from $1.540.37 Show details »

Eleuthera - 2x2 Fully Updated Old Town Waterfront Corner Condo in Key West, USA

Eleuthera - 2x2 Fully Updated Old Town W...

Holiday home in Key West near Stock Island, Florida , 915 Eisenhower Drive
Just a 17-minute walk from Rest Beach and one mile from Higgs Beach, Eleuthera - 2x2 Fully Updated Old Town Waterfront Corner Condo features accommoda...
  • Parking
  • Pets allowed
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Superb 18 Reviews 9.1

from $458.63 Show details »

Red Room at the Grand Maloney in Key West, USA

Red Room at the Grand Maloney

Holiday home in Key West near Stock Island, Florida , Caroline Street 529
Just a 18-minute walk from Fort Zachary Taylor State Park Beach and 1.1 miles from South Beach, Red Room at the Grand Maloney features accommodations ...
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Fabulous 3 Reviews 9.0

from $322.26 Show details »

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