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300+ stays

Stays in Summerland Key

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SUPERHOST
Entire house in Summerland Key
Acreage Multi-Million Beach Mansion w/ Pool
10 guests4 bedrooms11 beds3 baths
PoolAir conditioningKitchenWifi
Rating 4.70 out of 5;46 reviews
Price:$856 / night
SUPERHOST
Entire house in Cudjoe Key
Bring Your Boat! 2 BR/2BA Waterfront Paradise!
4 guests2 bedrooms2 beds2 baths
PoolAir conditioningKitchenWifi
Rating 4.93 out of 5;15 reviews
Price:$225 / night
Entire house in Cudjoe Key
OCEAN PARADISE AT VENTURE OUT + 4 BIKES/ 2 KAYAKS!
6 guests2 bedrooms3 beds2 baths
PoolAir conditioningKitchenWifi
Rating 4.88 out of 5;8 reviews
Price:$329 / night
Entire house in Cudjoe Key
Sunrise Supreme Paradise: your 2bdrm2bath vacation
6 guests2 bedrooms3 beds2 baths
PoolAir conditioningKitchenWifi
Rating 4.60 out of 5;10 reviews
Price:$211 / night
SUPERHOST
Boat in Key West
1984, 32 foot Irwin sailboat “Sea Raven Six”
4 guests1 bedroom4 beds1 bath
PoolAir conditioningKitchenWifi
Rating 4.83 out of 5;107 reviews
Price:$95 / night
Entire house in Cudjoe Key
Dog-friendly resort community home w/ shared pool, hot tub, & tennis court!
6 guests2 bedrooms4 beds2 baths
PoolAir conditioningKitchenWifi
Price:$303 / night
Entire house in Cudjoe Key
Ocean Front Home in Great Location
6 guests2 bedrooms3 beds2 baths
PoolAir conditioningKitchenWifi
Rating 4.52 out of 5;57 reviews
Price:$225 / night
Entire cottage in Cudjoe Key
POOL, HOT TUB, KAYAKS, 35 MIN TO KEY WEST
6 guests2 bedrooms2 beds1 bath
PoolAir conditioningKitchenWifi
Rating 4.53 out of 5;49 reviews
Price:$154 / night
Entire house in Cudjoe Key
VENTURE OUT Waterfront with dock/Gated community
6 guests2 bedrooms3 beds2 baths
PoolAir conditioningKitchenWifi
Rating 4.53 out of 5;55 reviews
Price:$315 / night
Entire cabin in Marathon
Cottage 07
2 guests1 bedroom1 bed1 bath
Air conditioningWifi
Rating 4.24 out of 5;17 reviews
Price:$111 / night
SUPERHOST
Entire guesthouse in Big Pine Key
Beautiful private camper situated amongst nature
2 guests1 bedroom1 bed1 bath
Air conditioningKitchenWifi
Rating 4.91 out of 5;138 reviews
Price:$91 / night
Resort room in Marathon
PRIVATE BEACH OPEN! OCEAN FRONT KING UNIT W/ POOL
2 guests1 bedroom1 bed1 bath
PoolAir conditioningWifi
Rating 5.0 out of 5;4 reviews
Price:$256 / night
Entire house in Summerland Key
New Listing! Summerland Canal-Front Escape w/ Pool
6 guests2 bedrooms3 beds1 bath
PoolAir conditioningKitchenWifi
Rating 4.20 out of 5;5 reviews
Price:$140 / night
Entire house in Little Torch Key
Charming Canal Home with Tropical Decor
8 guests3 bedrooms3 beds2 baths
Air conditioningKitchenWifi
Price:$135 / night
Entire house in Key West
Living the dream!
6 guests2 bedrooms2 beds2 baths
PoolAir conditioningKitchenWifi
Price:$225 / night
SUPERHOST
Entire guest suite in Marathon
Waterfront, Dock, Tiki Hut
2 guests1 bedroom1 bed1 bath
Air conditioningKitchenWifi
Rating 4.92 out of 5;159 reviews
Price:$166 / night
Entire cottage in Cudjoe Key
PALM TREE PARADISE AT VENTURE OUT + BIKES & KAYAKS
6 guests2 bedrooms3 beds1 bath
PoolAir conditioningKitchenWifi
Rating 4.64 out of 5;137 reviews
Price:$140 / night
Entire house in Cudjoe Key
VENTURE OUT 308 WATERFRONT /GATED COMMUNITY
6 guests2 bedrooms2 beds2 baths
PoolAir conditioningKitchenWifi
Rating 4.60 out of 5;52 reviews
Price:$223 / night
SUPERHOST
Boat in Key West
Hunter Cherubini Sailboat, “Seesea” 30 foot.
4 guests1 bedroom3 beds1 bath
PoolAir conditioningKitchenWifi
Rating 4.82 out of 5;267 reviews
Price:$106 / night
SUPERHOST
Entire house in Cudjoe Key
Daisy Space on a Cudjoe Key Canal
5 guests2 bedrooms2 beds2 baths
PoolAir conditioningKitchen
Rating 4.92 out of 5;49 reviews
Price:$233 / night
1 20 of 300+ places to stay
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