Stock Island Holiday Rentals: Short-Term Accommodations for Rent

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In three months

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Our top choices for Stock Island holiday rentals

A marina with boats docked, a small docked boat with a thatched roof, and a restaurant with outdoor seating overlooking the water.

1. Aqua Lodges at Hurricane Hole Marina

Stock Island

Kagni

HK$2,289 total

includes taxes & fees

3 Nov - 4 Nov

A beachside resort with a wooden deck, palm trees, and a sunset view.

2. Grand Marina Suite by Brightwild Waterfront

Stock Island

Pawel

HK$5,343 total

includes taxes & fees

3 Nov - 4 Nov

A wooden boardwalk leading to a building with a green roof, surrounded by palm trees and a body of water.

3. The Grenada Suite Pool View Private Balcony

Key West

Luis

HK$4,364 total

includes taxes & fees

30 Nov - 1 Dec

A pool area with a wooden deck, lounge chairs, and a waterfall feature.

4. Lighthouse Suites Collection

Old Town Key West

Melissa

HK$5,905 total

includes taxes & fees

13 Nov - 14 Nov

A modern house with a swimming pool, a balcony, and a well-maintained garden.

5. Contra House Key West

Old Town Key West

Rosalie

HK$9,377 total

includes taxes & fees

9 Nov - 10 Nov

A two-story beachfront house with a balcony, a covered outdoor seating area, and a small boat dock.

6. Atlantic View Luxury Villa with Pool

Summerland Key

Preetam

HK$7,656 total

includes taxes & fees

15 Nov - 16 Nov

A wooden pedestrian bridge over a water body, surrounded by lush greenery and palm trees.

7. Tortuga Suite Sparkling Pool Hot Tub

Key West

HK$4,410 total

includes taxes & fees

1 Dec - 2 Dec

A white two-story house with a balcony and a swimming pool.

8. Capmar House by Brightwild Huge Home Pool

Raccoon Key

Karen

HK$12,216 total

includes taxes & fees

3 Nov - 4 Nov

A spacious foyer with a wooden staircase, a console table with decorative items, and a view of the outdoors through a glass door.

9. Evershore House Pool Parking Dock

Raccoon Key

HK$12,216 total

includes taxes & fees

5 Nov - 6 Nov

A spacious living area with a large sofa, a coffee table, and a view of a balcony with a railing.

10. Mastway House by Brightwild Pool Dock

Raccoon Key

HK$12,216 total

includes taxes & fees

4 Nov - 5 Nov

A two-story house with a swimming pool, surrounded by greenery and palm trees.

11. Seagate House by Brightwild Waterfront w Dock

Raccoon Key

HK$12,216 total

includes taxes & fees

3 Nov - 4 Nov

A view through white blinds of a swimming pool area with a hot tub, surrounded by palm trees and a white fence.

12. Poolside Retreat by Brightwild Cottage w Pool

Old Town Key West

"My boyfriend and I booked this for our first anniversary together and I cannot stress enough to not book this listing. There was trash from people before us, back door was broken to get to the pool, air conditioning didn’t work (it was so hot inside that the glass was all fogged up it was like a sauna), and the blow dryer in the bathroom SHOCKED ME when I tried to plug it in, my boyfriend heard the sound of the shock loudly from two rooms away. Horrifying to say the least and when I reached out...

Julia

HK$3,934 total

includes taxes & fees

1 Dec - 2 Dec

A living room with two sofas, a coffee table, and a view of the outdoors.

13. Waterlane House by Brightwild Pool Boat Dock

Raccoon Key

HK$13,140 total

includes taxes & fees

8 Nov - 9 Nov

A spacious living area with a blue sofa, a grey armchair, and a wooden coffee table. Large sliding glass doors lead to a pool and outdoor furniture.

14. Suncoast House by Brightwild Pool Boat Dock

Raccoon Key

HK$14,475 total

includes taxes & fees

9 Nov - 10 Nov

A two-story house with a pool, surrounded by palm trees and a clear sky.

15. Mirador House by Brightwild Pool Dock

Raccoon Key

HK$14,475 total

includes taxes & fees

3 Nov - 4 Nov

A spacious kitchen with a large island, white cabinetry, and pendant lighting.

16. Aquaria House by Brightwild Pool Boat Dock

Raccoon Key

HK$13,140 total

includes taxes & fees

4 Nov - 5 Nov

A spacious kitchen with modern appliances, a dining area with a wooden table and chairs, and a view of a lake through large windows.

17. Springtide House by Brightwild Waterfront Pool

Raccoon Key

HK$13,140 total

includes taxes & fees

3 Nov - 4 Nov

A covered porch with a table and chairs, overlooking a street with houses and cars.

18. Banana Split by Brightwild Pool Grill

Key West Historic District

HK$3,837 total

includes taxes & fees

1 Dec - 2 Dec

A white two-story house with a central archway and a paved driveway.

19. Palmgale House in Key West

Raccoon Key

HK$16,456 total

includes taxes & fees

9 Nov - 10 Nov

A spacious living area with a wooden dining table, comfortable seating, a flat-screen TV, and large windows offering a view of the outdoors.

20. Spindrift House by Brightwild Huge Pool Dock

Raccoon Key

HK$13,140 total

includes taxes & fees

3 Nov - 4 Nov

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Top Stock Island Hotel Reviews

Opal Key Resort & Marina, Key West

10/10 Excellent

"have stayed here many times. nice location in old Town."

Southernmost Beach Resort and Guesthouses

8/10 Good

"We had a quick stay. Everything was clean and staff was nice. We needed to find a quiet work area for the next day and the evening/night staff was not informed or able to help us out. So instead that guest had to leave early. Other than that all was good. Jenn was very helpful in getting us a golf cart and giving recommendations. Fun activities."

DoubleTree Resort by Hilton Grand Key - Key West

8/10 Good

"El hotel esta muy bien lo mejor se todo es que llegamos a la 1 y tenían ya una habitación disponible para nosotros muy atentos, el unico inconveniente y no es una gran cosa es que el ventilador de techo de la habitación que nos tocó no funcionaba pero no fue un problema porque el aire acocionado funcionaba perfecto."

Hilton Key West Resort & Marina

8/10 Good

"The property and our stay was great - - - until check out, where we were presented with a surprise $578 bill for Taxes, Fees, and taxes on fees for a 3-day stay. They claim that since we booked thru a booking agent, Expedia, that those fees were not collected, and would not have been charged if we had booked direct. Basically, a penalty for booking thru Expedia. I had been aware of this Hotel if not for Expedia."

Find out more about Stock Island

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Be picky

Check prices for these dates

Our top choices for Stock Island holiday rentals

1. Aqua Lodges at Hurricane Hole Marina

2. Grand Marina Suite by Brightwild Waterfront

3. The Grenada Suite Pool View Private Balcony

4. Lighthouse Suites Collection

5. Contra House Key West

6. Atlantic View Luxury Villa with Pool

7. Tortuga Suite Sparkling Pool Hot Tub

8. Capmar House by Brightwild Huge Home Pool

9. Evershore House Pool Parking Dock

10. Mastway House by Brightwild Pool Dock

11. Seagate House by Brightwild Waterfront w Dock

12. Poolside Retreat by Brightwild Cottage w Pool

13. Waterlane House by Brightwild Pool Boat Dock

14. Suncoast House by Brightwild Pool Boat Dock

15. Mirador House by Brightwild Pool Dock

16. Aquaria House by Brightwild Pool Boat Dock

17. Springtide House by Brightwild Waterfront Pool

18. Banana Split by Brightwild Pool Grill

19. Palmgale House in Key West

20. Spindrift House by Brightwild Huge Pool Dock

Find holiday rentals that suit your style

Top Stock Island Hotel Reviews

Opal Key Resort & Marina, Key West

Winslow's Bungalows - Key West Historic Inns

Margaritaville Beach House Key West

Southernmost Beach Resort and Guesthouses

DoubleTree Resort by Hilton Grand Key - Key West

Blue Flamingo Resort Key West

Hilton Key West Resort & Marina

The Reach Key West, Curio Collection by Hilton

Parrot Key Hotel & Villas

Find out more about Stock Island

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