Holiday rentals in Stock Island

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Top-rated holiday rentals in Stock Island

Guests agree: these stays are highly rated for location, cleanliness and more.

Guest favourite

Home in Key West

4.94 out of 5 average rating, 268 reviews

Romantic Retreat - 2 person K Suite, Pvt deck/Spa!

Romantic Retreat is an Historic, free standing cottage which, in the 1800's, was the cistern for the Cigar Maker cottages here. It is decorated in a light Caribbean motif, efficiency kitchen (frig, microwave, hot plate) and a very airy bathroom with tub/shower. King memory foam bed and sleeps 2 persons only. 32” Smart TV (bring your Netflix, Amazon UN/PW's). Bose Bluetooth speaker, Amazon Alexa provided. A private adjacent deck with a 2 person Solana spa/seating. Also handicapped accessible.

4–11 Aug

£453 per night
Guest favourite

Flat in Key West

4.98 out of 5 average rating, 441 reviews

Bella Vita: 1B/1B Condo for 2 Just Steps off Duval

1B/1B condo located in Old Town less than 1/2 block from Duval St. & a couple blocks from the Southernmost Point, Hemingway House & many other Key West attractions. Bella Vita accommodates 2 adults only and features a large porch with chairs & table, living room with leather sofa, galley kitchen with bar seating, king-size bed with Tempurpedic mattress, desk area, bathroom with large walk-in shower, wi-fi, sound machine, 2 Smart TVs, DVD players & BlueTooth stereo system with CD player & radio.

20–27 Jan

£304 per night
Guest favourite

Townhouse in Key West

4.89 out of 5 average rating, 103 reviews

Charming Key West Vacation Rental 3bedrm/3bath

Beautiful gated home located in Coral Hammock just minutes away from Key West. It's a spacious 3 bedroom, 3 bath home with a full kitchen, living room, indoor and outdoor dining. With access to shared pool, club house and gym. Everything you need to enjoy vacation. We have also updated the unit with new flooring throughout! Beach Gear is also available. Beach towels, beach chairs, beach toys, floats and cooler. Baby / Toddler items available upon request. Portable Crib, high chair & more.

26 Jun – 3 Jul

£534 per night

Popular amenities for Stock Island holiday rentals

Stay near Stock Island's top sights

Boyd's Key West Campground6 locals recommend
Hogfish Bar & Grill87 locals recommend
Lazy Dog Adventures11 locals recommend
Hurricane Hole28 locals recommend
Roostica39 locals recommend
Chico's Cantina10 locals recommend

Other great holiday rentals in Stock Island

Superhost

Boat in Key West

4.79 out of 5 average rating, 68 reviews

The Escape- Private 2 Bed Rm Boat Beautiful Marina

24 Apr – 1 May

£223 per night
Guest favourite

Boat in Key West

5.0 out of 5 average rating, 29 reviews

Living the Dream, Key West Style

18–25 Apr

£313 per night
Guest favourite

Home in Key West

4.97 out of 5 average rating, 39 reviews

Gone Coastal

3–10 Dec

£442 per night
Guest favourite

Apartment in Key West

4.98 out of 5 average rating, 41 reviews

Oceanfront 3 bed condo Ocean Edge w/ optional slip

22 Feb – 1 Mar

£902 per night
Guest favourite

Apartment in Key West

4.99 out of 5 average rating, 83 reviews

Hidden Beach Duplex, Best Place in Key West

2–9 Aug

£586 per night
Guest favourite

Home in Key West

5.0 out of 5 average rating, 62 reviews

Clean and Relaxing! 3 King Suites! With everything

5–12 Jul

£724 per night
Guest favourite

Flat in Stock Island

4.86 out of 5 average rating, 14 reviews

Peaceful 1 bedroom at Leo's

25 Jun – 2 Jul

£302 per night
Superhost

Boat in Key West

5.0 out of 5 average rating, 4 reviews

The SeaRay Experience

21–28 Apr

£403 per night
Superhost

Home in Key West

4.87 out of 5 average rating, 23 reviews

Key West Paradise

15–22 Oct

£629 per night
Superhost

Home in Key West

5.0 out of 5 average rating, 3 reviews

Charming + Historic Eyebrow Home

24 Feb – 3 Mar

£523 per night
Guest favourite

Bungalow in Key West

4.99 out of 5 average rating, 76 reviews

Atlantis House's Palm Suite-voted top 25 in USA

14–21 Oct

£699 per night
Superhost

Houseboat in Key West

4.91 out of 5 average rating, 35 reviews

The Crystalmarine Suite – Rustic Luxury on the Sea

7–14 Feb

£439 per night

Quick stats about holiday rentals in Stock Island

Total rentals

110 properties

Rentals with a pool

60 properties have a pool

Pet-friendly rentals

30 properties allow pets

Family-friendly rentals

60 properties are a good fit for families

Total number of reviews

5.3K reviews

Nightly prices starting at

£55 before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Monroe County
  5. Stock Island