Holiday rentals near Pigeon Key
We found 1,537 holiday rentals — enter your dates for availability
If you'd like to stay close to Pigeon Key, take a look at holiday rentals to choose your home away from home. Whether you’re staying in a holiday home with family or friends, you'll have the best amenities for spending time at your home away from home, which might include a garden and pool. At the end of the day, you'll be sure to find a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.
Holiday rentals with weekly discounts - Pigeon Key
Showing deals for:21 Nov - 28 Nov
Image gallery for Finest location in Coral Lagoon. End unit with bay views and boat slip!
9.69.6 out of 10 rating
Exceptional
(182 reviews)
Finest location in Coral Lagoon. End unit with bay views and boat slip!
Marathon, FL
8% off
Price is AU$8,491
AU$8,491
AU$1,213 per night
includes taxes & fees
Image gallery for Private 4/3 Pool Heater/Dock/Kayaks/Bikes,etc
1010 out of 10 rating
Exceptional
(44 reviews)
Private 4/3 Pool Heater/Dock/Kayaks/Bikes,etc
Marathon, FL
8% off
Price is AU$8,288
AU$8,288
AU$1,184 per night
includes taxes & fees
Image gallery for New Paradise On Sombrero Beach
9.89.8 out of 10 rating
Exceptional
(26 reviews)
New Paradise On Sombrero Beach
Marathon, FL
8% off
Price is AU$7,294
AU$7,294
AU$1,042 per night
includes taxes & fees
Image gallery for 50% OFF~FALL BOOKINGS~POOL/ICE MACHINE, DOCK~DEEP H20 CANAL~C VIDEO OF OUR HOME!
1010 out of 10 rating
Exceptional
(40 reviews)
50% OFF~FALL BOOKINGS~POOL/ICE MACHINE, DOCK~DEEP H20 CANAL~C VIDEO OF OUR HOME!
Marathon, FL
6% off
Price is AU$7,364
AU$7,364
AU$1,052 per night
includes taxes & fees
Image gallery for Key West style cottage w/ dock overlooking Florida Bay. Wrap around windows!
9.89.8 out of 10 rating
Exceptional
(8 reviews)
Key West style cottage w/ dock overlooking Florida Bay. Wrap around windows!
Marathon, FL
8% off
Price is AU$5,762
AU$5,762
AU$823 per night
includes taxes & fees
Image gallery for Waterfront, dock, easy ocean access, heated pool, walk to beach! Great location!
9.49.4 out of 10 rating
Exceptional
(39 reviews)
Waterfront, dock, easy ocean access, heated pool, walk to beach! Great location!
Marathon, FL
7% off
Price is AU$4,864
AU$4,864
AU$695 per night
includes taxes & fees
Image gallery for ANY DAY CHECK-IN TIL DEC! Dock/Private Pool! Elevator! Walk to Beach! 5/5 Villa!
1010 out of 10 rating
Exceptional
(34 reviews)
ANY DAY CHECK-IN TIL DEC! Dock/Private Pool! Elevator! Walk to Beach! 5/5 Villa!
Marathon, FL
8% off
Price is AU$10,977
AU$10,977
AU$1,568 per night
includes taxes & fees
Image gallery for Private 2 Master Bedroom Suits, Sleeps 6, Heat/Chiller Pool, Quiet Neighborhood
9.89.8 out of 10 rating
Exceptional
(103 reviews)
Private 2 Master Bedroom Suits, Sleeps 6, Heat/Chiller Pool, Quiet Neighborhood
Marathon, FL
15% off
Price is AU$4,443
AU$4,443
AU$635 per night
includes taxes & fees
Image gallery for Beautiful Canal front w/ dock - private pool -4/3~walk to beach~Outdoor smart tv
9.69.6 out of 10 rating
Exceptional
(99 reviews)
Beautiful Canal front w/ dock - private pool -4/3~walk to beach~Outdoor smart tv
Marathon, FL
8% off
Price is AU$7,376
AU$7,376
AU$1,054 per night
includes taxes & fees
Image gallery for Tropical Retreat in the Heart of the Keys
9.89.8 out of 10 rating
Exceptional
(32 reviews)
Tropical Retreat in the Heart of the Keys
Marathon, FL
8% off
Price is AU$4,621
AU$4,621
AU$660 per night
includes taxes & fees
Image gallery for Waterfront Oasis w/ Pool, Tiki Lounge, Dock & BBQ
1010 out of 10 rating
Exceptional
(60 reviews)
Waterfront Oasis w/ Pool, Tiki Lounge, Dock & BBQ
Marathon, FL
8% off
Price is AU$5,240
AU$5,240
AU$749 per night
includes taxes & fees
Image gallery for 10-20%off remaining summer weeks-Flamingo Palms updated, canal to Sombrero
1010 out of 10 rating
Exceptional
(6 reviews)
10-20%off remaining summer weeks-Flamingo Palms updated, canal to Sombrero
Marathon, FL
7% off
Price is AU$3,384
AU$3,384
AU$483 per night
includes taxes & fees
Image gallery for Ocean View & Canal Access Home with Jacuzzi
1010 out of 10 rating
Exceptional
(17 reviews)
Ocean View & Canal Access Home with Jacuzzi
Marathon, FL
8% off
Price is AU$4,299
AU$4,299
AU$614 per night
includes taxes & fees
Image gallery for KEY COLONY BEACH Island Paradise! 80FT DOCK. 331
9.29.2 out of 10 rating
Wonderful
(18 reviews)
KEY COLONY BEACH Island Paradise! 80FT DOCK. 331
Key Colony Beach, FL
12% off
Price is AU$5,002
AU$5,002
AU$715 per night
includes taxes & fees
Image gallery for Casa Solis with 30' dock on the ocean side.
9.89.8 out of 10 rating
Exceptional
(111 reviews)
Casa Solis with 30' dock on the ocean side.
Marathon, FL
8% off
Price is AU$2,952
AU$2,952
AU$422 per night
includes taxes & fees
Image gallery for Tropical Paradise 🏝! POOL, Hot Tub, Dock, FREE Ice, Kayaks, Paddles, Bikes!
9.69.6 out of 10 rating
Exceptional
(26 reviews)
Tropical Paradise 🏝! POOL, Hot Tub, Dock, FREE Ice, Kayaks, Paddles, Bikes!
Key Colony Beach, FL
8% off
Price is AU$3,703
AU$3,703
AU$529 per night
includes taxes & fees
Image gallery for SUMMER Discounts-Blue Ocean Bungalow 3bdr./3ba. updated canal access Sombrero
1010 out of 10 rating
Exceptional
(16 reviews)
SUMMER Discounts-Blue Ocean Bungalow 3bdr./3ba. updated canal access Sombrero
Marathon, FL
7% off
Price is AU$3,936
AU$3,936
AU$562 per night
includes taxes & fees
Image gallery for Casablanca
9.49.4 out of 10 rating
Exceptional
(8 reviews)
Casablanca
Key Colony Beach, FL
7% off
Price is AU$3,095
AU$3,095
AU$442 per night
includes taxes & fees
Image gallery for Convenient central Marathon location, canal view.
9.69.6 out of 10 rating
Exceptional
(49 reviews)
Convenient central Marathon location, canal view.
Marathon, FL
7% off
Price is AU$1,754
AU$1,754
AU$251 per night
includes taxes & fees
Image gallery for Key Colony Home with Dock and Cabana Club Access- Pets Welcomed
9.89.8 out of 10 rating
Exceptional
(15 reviews)
Key Colony Home with Dock and Cabana Club Access- Pets Welcomed
Key Colony Beach, FL
8% off
Price is AU$5,048
AU$5,048
AU$721 per night
includes taxes & fees
Image gallery for RELAX AWAY- NEW 4BDRM W/ 40FT DOCK & PRIVATE POOL
9.69.6 out of 10 rating
Exceptional
(53 reviews)
RELAX AWAY- NEW 4BDRM W/ 40FT DOCK & PRIVATE POOL
Marathon, FL
7% off
Price is AU$6,439
AU$6,439
AU$920 per night
includes taxes & fees
Image gallery for KCB-access Private Cabana Club,Dock on Canal,PET Friendly, Pickle ball courts
9.49.4 out of 10 rating
Exceptional
(61 reviews)
KCB-access Private Cabana Club,Dock on Canal,PET Friendly, Pickle ball courts
Key Colony Beach, FL
7% off
Price is AU$2,999
AU$2,999
AU$428 per night
includes taxes & fees
Image gallery for Access to Cabana Club/Private beach
1010 out of 10 rating
Exceptional
(11 reviews)
Access to Cabana Club/Private beach
Key Colony Beach, FL
7% off
Price is AU$4,779
AU$4,779
AU$683 per night
includes taxes & fees
Image gallery for Canal Home with Direct Ocean Access, 75' dock, Hammock, Coconut Trees & More🌴
1010 out of 10 rating
Exceptional
(160 reviews)
Canal Home with Direct Ocean Access, 75' dock, Hammock, Coconut Trees & More🌴
Marathon, FL
8% off
Price is AU$3,522
AU$3,522
AU$503 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Pigeon Key
Sale! 25% off August days: Coral Lagoon #13: Pool, Water Views, at Vaca Cut
Sleeps 8 · 3 bedrooms · 2+ bathrooms
1010 out of 10
Exceptionalexceptional
262 reviews(262 reviews)
New Listing! East facing home on widest water canal! Beautiful, cool sunrises!
Sleeps 4 · 2 bedrooms · 2 bathrooms
9.29.2 out of 10
Wonderfulwonderful
30 reviews(30 reviews)
Relax with Incredible Ocean and Sunset Views - Cabana Club
Sleeps 4 · 2 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
14 reviews(14 reviews)
Lo-Key 1: Discover Your Slice of Paradise, Charming Marathon Home, Pool, Deck, Patio & Dog-Friendly!
Sleeps 8 · 3 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
21 reviews(21 reviews)
Beautiful oceanfront home with dock and kayaks!
Sleeps 8 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
24 reviews(24 reviews)
FALL SPECIAL 40% off Rental Rate! Sep-Dec 2025 except holidays
Sleeps 12 · 5 bedrooms · 4 bathrooms
9.69.6 out of 10
Exceptionalexceptional
125 reviews(125 reviews)
Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value