Cottage holiday rentals in Monroe County
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Top-rated cottage rentals in Monroe County
Guests agree: these cottages are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for cottage rentals in Monroe County
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
2–9 Sep
Cottage in Cudjoe Key
4.84 out of 5 average rating, 32 reviewsTidewater Views @ Venture Out - Waterfront
16–23 Nov
Cottage in Key Colony Beach
4.5 out of 5 average rating, 6 reviews2BR dog-friendly water view stay, resort amenities
29 Nov – 6 Dec
Cottage in Cudjoe Key
4.6 out of 5 average rating, 93 reviewsVO Community 501 Midrise 2Bd/1.5Ba Large Open Deck
21–28 Sep
Cottage in Cudjoe Key
4.57 out of 5 average rating, 7 reviewsWalk to the Pool - Venture Out Unit 333
21–28 May
Cottage in Cudjoe Key
4.71 out of 5 average rating, 119 reviewsCalypso Cottage
27 Nov – 4 Dec
Cottage in Islamorada
Adorable Cottage w/ Dock, Pool & Beach!VR24-0106
22–29 Nov
Cottage in Cudjoe Key
4.83 out of 5 average rating, 84 reviewsOCEANIA... water front cottage retreat ~
23–30 Nov
Pet-friendly cottage rentals
Cottage in Miami
4.92 out of 5 average rating, 12 reviewsCozy cottage garden & parking
17–24 Jul
Cottage in Key Largo
4.96 out of 5 average rating, 55 reviews2 BR with private Tiki Boat dock for 25' boat max
31 Mar – 7 Apr
Cottage in Miami
4.91 out of 5 average rating, 70 reviewsCottage-Private Gated Estate w/heated Pool Near UM
9–16 Oct
Cottage in Key Largo
4.94 out of 5 average rating, 32 reviewsSpacious cottage in the heart of the keys
28 Oct – 4 Nov
Cottage in Marathon
5.0 out of 5 average rating, 3 reviewsPrime Location 1B/1B Home
13–20 Apr
Cottage in Homestead
4.62 out of 5 average rating, 13 reviewsLarge, secluded 2-bedroom house with private yard
18–25 Mar
Cottage in Islamorada
4.83 out of 5 average rating, 6 reviewsOcean Front Cottage
6–13 Dec
Cottage in Key Largo
4.89 out of 5 average rating, 28 reviewsKayaking, sailing, snorkeling Free w/ Cottage
5–12 Sep
Private cottage rentals
Cottage in Marathon
4.95 out of 5 average rating, 22 reviewsCatch n' Relax Canalfront Cottage in Marathon
25 Oct – 1 Nov
Cottage in Miami
4.62 out of 5 average rating, 303 reviewsHistoric Casa Havana - Studio Cottage
4–11 Jun
Cottage in Marathon
4.96 out of 5 average rating, 25 reviewsWATER FRONT COTTAGE W/ MOTHER IN LAW TREETOP SUITE
22–29 Aug
Cottage in Miami
4.85 out of 5 average rating, 55 reviewsThe Cottage
20–27 Sep
Cottage in Key West
4.74 out of 5 average rating, 337 reviews1 bedroom Cottage
14–21 Jul
Cottage in Key Largo
5.0 out of 5 average rating, 26 reviewsCottage home in the heart of Key Largo
23–30 Mar
Cottage in Key Largo
5.0 out of 5 average rating, 6 reviewsOcean Shores Cottage: Heated private Pool-OS canal
25 Jan – 1 Feb
Cottage in Miami
4.88 out of 5 average rating, 66 reviewsCharming Coconut Grove Cottage
10–17 May
Destinations to explore
- Cottage rentals Miami
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