Shark Key vacation rentals

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Top-rated vacation rentals in Shark Key

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

Guest favorite

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.

Aug 4 – 11

G$105,090 GYD per night
Superhost

Cottage in Cudjoe Key

4.92 out of 5 average rating, 130 reviews

ATLANTIS...Ocean Front Cottage Retreat!

ATLANTIS~An ocean front cottage retreat! Completely remodeled, direct ocean-front cottage offers everything you'll need for the perfect getaway. Boat dock (25ft), HD TVs, washer & dryer, S/S appliances & gas cooking! Complimentary kayaks & bikes plus access to all the Venture Out Residential Condominium Community amenities: heated pool, Jacuzzi, kiddie pool, tennis, basketball & bocce courts, ocean bay swimming area, marina w/fuel, boat ramps & wash station, and a convenience market on-site!

Dec 28 – Jan 4

G$158,383 GYD per night
Guest favorite

Apartment 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.

Jan 20 – 27

G$71,088 GYD per night

Popular amenities for Shark Key vacation rentals

Other great vacation rentals in Shark Key

Guest favorite

Cottage in Islamorada

4.85 out of 5 average rating, 124 reviews

1 BD PRIVATE HOUSEBOAT/ COTTAGE TARPON

Nov 16 – 23

G$40,958 GYD per night
Superhost

Villa in Marathon

4.89 out of 5 average rating, 141 reviews

New Aqua Lodge 2Beds 1 Bath with Full Kitchens

Sep 2 – 9

G$79,140 GYD per night
Guest favorite

Condo in Key West

4.94 out of 5 average rating, 33 reviews

Condo de Paradise/Salt Water Pool/Boat Dock

Apr 2 – 9

G$84,468 GYD per night
Superhost

Tiny home in Big Pine Key

4.8 out of 5 average rating, 88 reviews

Breezy pines 28 foot 5th wheel trailer .

Oct 16 – 23

G$24,717 GYD per night
Guest favorite

Guest suite in Key Colony Beach

4.99 out of 5 average rating, 81 reviews

Turtle-By-The-Sea: the Best Deal in KCB!

May 3 – 10

G$37,659 GYD per night
Superhost

Home in Upper Sugarloaf Key

4.86 out of 5 average rating, 43 reviews

Bungalows at Sugarloaf Beach - The Lighthouse

Aug 6 – 13

G$186,537 GYD per night
Guest favorite

Condo in Key West

4.99 out of 5 average rating, 83 reviews

Hidden Beach Duplex, Best Place in Key West

Aug 2 – 9

G$145,202 GYD per night
Guest favorite

Home in Marathon

4.97 out of 5 average rating, 31 reviews

Beach House, Private Pool & Dock, Gulf Sunset view

Nov 9 – 16

G$117,220 GYD per night
Superhost

Home in Cudjoe Key

4.84 out of 5 average rating, 38 reviews

*Emerald Seas*-Florida Keys Ocean Front Paradise!

Jul 29 – Aug 5

G$155,994 GYD per night
Guest favorite

Home in Marathon

5.0 out of 5 average rating, 8 reviews

Million Dollar View

Oct 12 – 19

G$163,342 GYD per night
Superhost

Cottage in Key West

4.95 out of 5 average rating, 84 reviews

Mango Cottage 2 bedroom 2 bath with private pool

Oct 1 – 8

G$143,101 GYD per night
Superhost

Houseboat in Key West

4.91 out of 5 average rating, 35 reviews

The Crystalmarine Suite – Rustic Luxury on the Sea

Feb 7 – 14

G$108,752 GYD per night

Other great vacation rentals in Shark Key

Guest favorite

Home in Marathon

4.97 out of 5 average rating, 31 reviews

The Gulf Cottage at Marathon Key

Jun 7 – 14

G$31,234 GYD per night
Guest favorite

Home in Cudjoe Key

4.91 out of 5 average rating, 23 reviews

Relaxing and Inviting home with 35' dock

Jun 4 – 11

G$47,593 GYD per night
Guest favorite

Bungalow in Islamorada

4.96 out of 5 average rating, 28 reviews

Dream in Paradise! King Master, Queen Guest, Pool

Aug 22 – 29

G$138,975 GYD per night
Guest favorite

Home in Marathon

5.0 out of 5 average rating, 29 reviews

100' Dockage, Pool, Kayaks, Paddle Board, Bikes!

Oct 23 – 30

G$105,019 GYD per night
Guest favorite

Cottage in Cudjoe Key

4.91 out of 5 average rating, 74 reviews

King Master, 2BR, 2BA, 35' Seawall, SUP, Kayaks

Feb 24 – Mar 3

G$174,531 GYD per night
Superhost

Home in Key West

4.95 out of 5 average rating, 39 reviews

Southard Comfort ~ Feel The Key West Vibe

Sep 11 – 18

G$151,314 GYD per night
Guest favorite

Camper/RV in Big Pine Key

4.91 out of 5 average rating, 34 reviews

Having fun in the lower Keys

Jul 31 – Aug 7

G$34,485 GYD per night
Guest favorite

Boat in Key West

5.0 out of 5 average rating, 29 reviews

Living the Dream, Key West Style

Apr 18 – 25

G$77,441 GYD per night
Guest favorite

Home in Key West

5.0 out of 5 average rating, 13 reviews

Villa Paradiso: A unique mid-town paradise

May 11 – 18

G$189,503 GYD per night
Superhost

Home in Cudjoe Key

5.0 out of 5 average rating, 3 reviews

Latitudes-Ocean Front Pool

Sep 28 – Oct 5

G$143,985 GYD per night
Guest favorite

Home in Key Colony Beach

4.98 out of 5 average rating, 44 reviews

Captain’s Quarters Ahoy Mateys! Florida, Keys

Oct 1 – 8

G$51,805 GYD per night
Superhost

Home in Cudjoe Key

4.84 out of 5 average rating, 45 reviews

Spanish Queen @Venture Out

Aug 23 – 30

G$80,190 GYD per night

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Monroe County
  5. Shark Key