Cottage vacation rentals in Monroe County
Find and book unique cottages on Airbnb
Top-rated cottage rentals in Monroe County
Guests agree: these cottages are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Monroe County cottage rentals
Cottage rentals with a hot tub
Cottage in Cudjoe Key
4.91 out of 5 average rating, 79 reviewsKing Master, 2BR, 2BA, 35' Seawall, SUP, Kayaks
Jul 19 – 26
Cottage in Key West
4.82 out of 5 average rating, 22 reviewsDarling of Duval @ Old Town - Adorable Cottage
Sep 13 – 20
Cottage in Cudjoe Key
4.6 out of 5 average rating, 93 reviewsVO Community 501 Midrise 2Bd/1.5Ba Large Open Deck
Jan 12 – 19
Cottage in Cudjoe Key
4.71 out of 5 average rating, 119 reviewsCalypso Cottage
Dec 13 – 20
Cottage in Key Colony Beach
4.5 out of 5 average rating, 6 reviews2BR dog-friendly water view stay, resort amenities
Nov 21 – 28
Cottage in Cudjoe Key
4.57 out of 5 average rating, 7 reviewsWalk to the Pool - Venture Out Unit 333
Dec 15 – 22
Cottage in Islamorada
Adorable Cottage w/ Dock, Pool & Beach!VR24-0106
Nov 22 – 29
Cottage in Cudjoe Key
4.93 out of 5 average rating, 45 reviewsNAUTILUS...ocean front cottage retreat ~
Oct 27 – Nov 3
Pet-friendly cottage rentals
Cottage in Coral Gables
5.0 out of 5 average rating, 37 reviewsNew Modern Near Airport - Cozy Very Clean
Nov 12 – 19
Cottage in Miami
4.92 out of 5 average rating, 12 reviewsCozy cottage garden & parking
Jun 24 – Jul 1
Cottage in Key Largo
4.96 out of 5 average rating, 56 reviews2 BR with private Tiki Boat dock for 25' boat max
Nov 24 – Dec 1
Cottage in Miami
4.91 out of 5 average rating, 70 reviewsCottage-Private Gated Estate w/heated Pool Near UM
Oct 14 – 21
Cottage in Key Largo
4.94 out of 5 average rating, 33 reviewsSpacious cottage in the heart of the keys
Jan 18 – 25
Cottage in Homestead
4.62 out of 5 average rating, 13 reviewsLarge, secluded 2-bedroom house with private yard
Mar 29 – Apr 5
Cottage in Marathon
5.0 out of 5 average rating, 3 reviewsPrime Location 1B/1B Home
Feb 20 – 27
Cottage in Islamorada
4.83 out of 5 average rating, 6 reviewsOcean Front Cottage
Dec 6 – 13
Private cottage rentals
Cottage in Miami
4.62 out of 5 average rating, 303 reviewsHistoric Casa Havana - Studio Cottage
Jun 16 – 23
Cottage in Marathon
4.96 out of 5 average rating, 25 reviewsWATER FRONT COTTAGE W/ MOTHER IN LAW TREETOP SUITE
Dec 13 – 20
Cottage in Miami
4.86 out of 5 average rating, 56 reviewsThe Cottage
Nov 13 – 20
Cottage in Key West
4.74 out of 5 average rating, 338 reviews1 bedroom Cottage
Jul 15 – 22
Cottage in Key Largo
5.0 out of 5 average rating, 26 reviewsCottage home in the heart of Key Largo
Mar 29 – Apr 5
Cottage in Key Largo
5.0 out of 5 average rating, 6 reviewsOcean Shores Cottage: Heated private Pool-OS canal
Jan 25 – Feb 1
Cottage in Miami
4.88 out of 5 average rating, 67 reviewsCharming Coconut Grove Cottage
Sep 20 – 27
Cottage in Miami
4.83 out of 5 average rating, 69 reviewsHistoric Cottage in the Heart of the Grove
Sep 18 – 25
Destinations to explore
- Cottage rentals Miami
- Cottage rentals Florida
- Cottage rentals Fort Lauderdale
- Rentals with a home theater Monroe County
- Smoking-friendly rentals Monroe County
- Rentals with a sauna Monroe County
- Rentals with beach access Monroe County
- Rentals with an accessible height bed Monroe County
- Rentals with breakfast Monroe County
- Rentals with lake access Monroe County
- Serviced apartment rentals Monroe County
- Private suite rentals Monroe County
- Boat rentals Monroe County
- Beachfront rentals Monroe County
- Family-friendly rentals Monroe County
- Wheelchair accessible rentals Monroe County
- Waterfront rentals Monroe County
- Rentals with a fireplace Monroe County
- Ski-in/ski-out rentals Monroe County
- Rentals with pools Monroe County
- Rentals with an EV charger Monroe County
- Rentals with a washer and dryer Monroe County
- Tiny house rentals Monroe County
- RV rentals Monroe County
- Apartment rentals Monroe County
- Loft rentals Monroe County
- Campsite rentals Monroe County
- Fitness-friendly rentals Monroe County
- Rentals with a patio Monroe County
- Rentals with a hot tub Monroe County
- Kid-friendly rentals Monroe County
- Rentals with an accessible height toilet Monroe County
- Villa rentals Monroe County
- House rentals Monroe County
- Pet-friendly rentals Monroe County
- Townhouse rentals Monroe County
- Monthly Rentals Monroe County
- Farmstay rentals Monroe County
- Bed and breakfasts Monroe County
- Rentals with outdoor seating Monroe County
- Hotel rentals Monroe County
- Rentals with a fire pit Monroe County
- Rentals with a kayak Monroe County
- Houseboat rentals Monroe County
- Condo rentals Monroe County
- Guesthouse rentals Monroe County
- Luxury rentals Monroe County
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes