Hotels with a Pool in Key West
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Hotels with a Pool in Key West
Hampton Inn Key West FL
Hampton Inn Key West FL2.5 star property
Key West
- Outdoor pool
- Poolside bar
- Pool loungers
- Near the beach
9.0 out of 10, Wonderful, (1,377 reviews)
9.0/10
Wonderful
(1,377 reviews)
Sparkling waters invite relaxation at this outdoor pool oasis, complete with plush sun loungers and protective umbrellas. Swimming enthusiasts appreciate the clean, spacious deck, while the poolside restaurant serves delicious meals with ocean panoramas.
Sparkling waters invite relaxation at this outdoor pool oasis, complete with plush sun loungers and protective umbrellas. Swimming enthusiasts appreciate the clean, spacious deck, while the poolside restaurant serves delicious meals with ocean panoramas.
The price is $179
$179
$201 total
includes taxes & fees
Jun 7 - Jun 8
The Reach Key West, Curio Collection by Hilton
The Reach Key West, Curio Collection by Hilton4.0 star property
Old Town Key West
- Outdoor pool
- Poolside bar
- Pool loungers
- On private beach
- Full-service spa
8.6 out of 10, Excellent, (1,008 reviews)
8.6/10
Excellent
(1,008 reviews)
Bask poolside with a tropical cocktail after exploring Key West's water activities. A full-service spa, fitness center, and beachfront dining complement the sun-soaked atmosphere at this resort featuring water sports and yoga classes.
Bask poolside with a tropical cocktail after exploring Key West's water activities. A full-service spa, fitness center, and beachfront dining complement the sun-soaked atmosphere at this resort featuring water sports and yoga classes.
The price is $187
$187
$278 total
includes taxes & fees
Jul 1 - Jul 2
The Perry Hotel & Marina Key West
The Perry Hotel & Marina Key West4.0 star property
Stock Island
- 2 outdoor pools
- 2 poolside bars
- Pool loungers
9.4 out of 10, Exceptional, (1,272 reviews)
9.4/10
Exceptional
(1,272 reviews)
Sparkling pools frame this waterfront escape where poolside bars serve refreshing drinks between marina adventures. Spacious rooms with furnished balconies overlook stunning sunset views, complementing the exceptional onsite seafood restaurants.
Sparkling pools frame this waterfront escape where poolside bars serve refreshing drinks between marina adventures. Spacious rooms with furnished balconies overlook stunning sunset views, complementing the exceptional onsite seafood restaurants.
The price is $151
$151
$230 total
includes taxes & fees
Jul 2 - Jul 3
Beachside Resort & Residences
Beachside Resort & Residences3.5 star property
Key West
- Outdoor pool
- Poolside bar
- Pool loungers
- On private beach
- Hot tub
8.6 out of 10, Excellent, (2,269 reviews)
8.6/10
Excellent
(2,269 reviews)
Sparkling waters beckon at the marina-side pool complex, featuring loungers, umbrellas, and attentive poolside service. Kayaking adventures, white sand beaches, and a relaxing hot tub create perfect vacation days with stunning sunset views.
Sparkling waters beckon at the marina-side pool complex, featuring loungers, umbrellas, and attentive poolside service. Kayaking adventures, white sand beaches, and a relaxing hot tub create perfect vacation days with stunning sunset views.
The price is $138
$138
$250 total
includes taxes & fees
Jun 7 - Jun 8
The Laureate Key West
The Laureate Key West3.5 star property
New Town
- Outdoor pool
- Indoor pool
- Pool loungers
9.2 out of 10, Wonderful, (1,014 reviews)
9.2/10
Wonderful
(1,014 reviews)
Swimming options abound at these pristine indoor and outdoor pools surrounded by comfortable sun loungers and shaded umbrellas. Steps from Smathers Beach, guests relish stunning ocean views from private balconies after exciting water adventures.
Swimming options abound at these pristine indoor and outdoor pools surrounded by comfortable sun loungers and shaded umbrellas. Steps from Smathers Beach, guests relish stunning ocean views from private balconies after exciting water adventures.
The price is $159
$159
$207 total
includes taxes & fees
Jun 7 - Jun 8
9.4 out of 10, Exceptional, (1,035 reviews)
9.4/10
Exceptional
(1,035 reviews)
Swimming bliss awaits at the heated pool, surrounded by beautiful gardens that create a peaceful retreat. Nearby attractions include Ernest Hemingway Home and Duval Street, while bicycle rentals make exploring the island effortless.
Swimming bliss awaits at the heated pool, surrounded by beautiful gardens that create a peaceful retreat. Nearby attractions include Ernest Hemingway Home and Duval Street, while bicycle rentals make exploring the island effortless.
The price is $179
$179
$223 total
includes taxes & fees
Jun 8 - Jun 9
Casa Marina Key West, Curio Collection by Hilton
Casa Marina Key West, Curio Collection by Hilton4.0 star property
Old Town Key West
- 2 outdoor pools
- Pool loungers
- On private beach
- Full-service spa
8.4 out of 10, Very Good, (688 reviews)
8.4/10
Very Good
(688 reviews)
Pool loungers dot the water's edge at this oceanfront haven featuring 2 outdoor swimming pools and a private beach sanctuary. Beach volleyball, water sports, and pool umbrellas create the perfect balance of activity and relaxation.
Pool loungers dot the water's edge at this oceanfront haven featuring 2 outdoor swimming pools and a private beach sanctuary. Beach volleyball, water sports, and pool umbrellas create the perfect balance of activity and relaxation.
The price is $256
$256
$355 total
includes taxes & fees
Jun 17 - Jun 18
Parrot Key Hotel & Villas
Parrot Key Hotel & Villas4.0 star property
Northside Resort
- 4 outdoor pools
- Poolside bar
- Pool loungers
9.0 out of 10, Wonderful, (1,413 reviews)
9.0/10
Wonderful
(1,413 reviews)
Splash into vacation mode at any of the 4 beautifully maintained pools, each offering the perfect temperature for ultimate relaxation. After swimming, sip cocktails at the poolside bar or dine at the waterfront restaurant while admiring spectacular sunset views.
Splash into vacation mode at any of the 4 beautifully maintained pools, each offering the perfect temperature for ultimate relaxation. After swimming, sip cocktails at the poolside bar or dine at the waterfront restaurant while admiring spectacular sunset views.
The price is $159
$159
$236 total
includes taxes & fees
Jun 15 - Jun 16
Ocean Key Resort - A Noble House Resort
Ocean Key Resort - A Noble House Resort4.0 star property
Key West Historic District
- Outdoor pool
- Poolside bar
- Pool loungers
- Near the beach
- Full-service spa
9.2 out of 10, Wonderful, (1,000 reviews)
9.2/10
Wonderful
(1,000 reviews)
Floating serenely in the outdoor pool, guests admire breathtaking Key West sunsets while sipping cocktails from the poolside bar. Spa treatments, water sports rentals, and yoga classes complete this luxurious oceanfront escape.
Floating serenely in the outdoor pool, guests admire breathtaking Key West sunsets while sipping cocktails from the poolside bar. Spa treatments, water sports rentals, and yoga classes complete this luxurious oceanfront escape.
The price is $303
$303
$418 total
includes taxes & fees
Jun 23 - Jun 24
Silver Palms Inn & Historic Homes
Silver Palms Inn & Historic Homes3.5 star property
Old Town Key West
- Outdoor pool
- Near the beach
9.4 out of 10, Exceptional, (1,039 reviews)
9.4/10
Exceptional
(1,039 reviews)
Soak up rays at the immaculate outdoor pool, complete with comfortable lounging areas for post-exploration relaxation. On-site bicycle rentals make discovering Key West effortless, while the convenient location puts Duval Street within easy reach.
Soak up rays at the immaculate outdoor pool, complete with comfortable lounging areas for post-exploration relaxation. On-site bicycle rentals make discovering Key West effortless, while the convenient location puts Duval Street within easy reach.
The price is $112
$112
$193 total
includes taxes & fees
Jun 8 - Jun 9
Hilton Garden Inn Key West / The Keys Collection
Hilton Garden Inn Key West / The Keys Collection3.5 star property
New Town
- Outdoor pool
- Poolside bar
- Pool loungers
- Hot tub
8.0 out of 10, Very Good, (1,230 reviews)
8.0/10
Very Good
(1,230 reviews)
Soak up sunshine at the resort-style outdoor pool with its relaxing cabanas, perfect for unwinding with a cool drink after exploring nearby attractions. Complimentary shuttles make reaching local sights effortless, while on-site dining completes the experience.
Soak up sunshine at the resort-style outdoor pool with its relaxing cabanas, perfect for unwinding with a cool drink after exploring nearby attractions. Complimentary shuttles make reaching local sights effortless, while on-site dining completes the experience.
The price is $115
$115
$157 total
includes taxes & fees
Jun 21 - Jun 22
Blue Flamingo Resort Key West
Blue Flamingo Resort Key West4.0 star property
New Town
- 2 outdoor pools
- 2 poolside bars
- Pool loungers
- Hot tub
8.4 out of 10, Very Good, (2,322 reviews)
8.4/10
Very Good
(2,322 reviews)
Splashing into paradise starts at the 2 outdoor pools surrounded by swaying palms and cabanas. Grab drinks from poolside bars, play mini golf, then catch stunning sunsets from the terrace after exploring nearby Key West attractions.
Splashing into paradise starts at the 2 outdoor pools surrounded by swaying palms and cabanas. Grab drinks from poolside bars, play mini golf, then catch stunning sunsets from the terrace after exploring nearby Key West attractions.
The price is $125
$125
$197 total
includes taxes & fees
Jun 7 - Jun 8
DoubleTree Resort by Hilton Grand Key - Key West
DoubleTree Resort by Hilton Grand Key - Key West4.0 star property
Key West
- Outdoor pool
- Poolside bar
- Pool loungers
- Near the beach
8.4 out of 10, Very Good, (1,031 reviews)
8.4/10
Very Good
(1,031 reviews)
Poolside perfection awaits with refreshing cocktails served right to your cabana. Guests praise the huge, beautiful pool surrounded by plentiful seating. After swimming, enjoy American cuisine at Palm Haven restaurant with al fresco dining options.
Poolside perfection awaits with refreshing cocktails served right to your cabana. Guests praise the huge, beautiful pool surrounded by plentiful seating. After swimming, enjoy American cuisine at Palm Haven restaurant with al fresco dining options.
The price is $147
$147
$199 total
includes taxes & fees
Jun 28 - Jun 29
Margaritaville Beach House Key West
Margaritaville Beach House Key West4.0 star property
Key West
- Outdoor pool
- Direct access to the beach
8.8 out of 10, Excellent, (1,813 reviews)
8.8/10
Excellent
(1,813 reviews)
Kayaking, snorkeling, and beach bliss create perfect days at this tranquil retreat. After water adventures, guests relish poolside relaxation surrounded by tropical gardens before savoring delicious meals at the on-site restaurant.
Kayaking, snorkeling, and beach bliss create perfect days at this tranquil retreat. After water adventures, guests relish poolside relaxation surrounded by tropical gardens before savoring delicious meals at the on-site restaurant.
The price is $225
$225
$316 total
includes taxes & fees
Jun 28 - Jun 29
Havana Cabana at Key West
Havana Cabana at Key West4.0 star property
New Town
- Outdoor pool
- Poolside bar
- Pool loungers
- Hot tub
9.0 out of 10, Wonderful, (1,792 reviews)
9.0/10
Wonderful
(1,792 reviews)
Soak up the sun on pool loungers while sipping Cuban-inspired cocktails from the poolside bar. After refreshing dips in the sparkling outdoor pool, unwind in the relaxing hot tub before savoring delicious meals from the Floridita Food Truck.
Soak up the sun on pool loungers while sipping Cuban-inspired cocktails from the poolside bar. After refreshing dips in the sparkling outdoor pool, unwind in the relaxing hot tub before savoring delicious meals from the Floridita Food Truck.
The price is $128
$128
$209 total
includes taxes & fees
Jul 5 - Jul 6
Simonton Court Historic Inn & Cottages
Simonton Court Historic Inn & Cottages2.5 star property
Key West Historic District
- 4 outdoor pools
- Pool loungers
- Near the beach
9.8 out of 10, Exceptional, (970 reviews)
9.8/10
Exceptional
(970 reviews)
The price is $149
$149
$168 total
includes taxes & fees
Jun 7 - Jun 8
Authors of Key West Guest House
Authors of Key West Guest House3.0 star property
Key West Historic District
- Outdoor pool
- Pool loungers
- Near the beach
9.2 out of 10, Wonderful, (1,007 reviews)
9.2/10
Wonderful
(1,007 reviews)
Splash into vacation mode in the inviting outdoor pool, complete with sun loungers perfect for afternoon relaxation. Situated near Ernest Hemingway's Home, this bed & breakfast offers continental breakfast and bike rental assistance for island adventures.
Splash into vacation mode in the inviting outdoor pool, complete with sun loungers perfect for afternoon relaxation. Situated near Ernest Hemingway's Home, this bed & breakfast offers continental breakfast and bike rental assistance for island adventures.
The price is $119
$119
$134 total
includes taxes & fees
Jun 8 - Jun 9
Ibis Bay Beach Resort
Ibis Bay Beach Resort2.5 star property
Northside Resort
- Outdoor pool
- Poolside bar
- Pool loungers
- On private beach
8.0 out of 10, Very Good, (2,289 reviews)
8.0/10
Very Good
(2,289 reviews)
Sparkling blue waters beckon from the outdoor pool, complete with plush sun loungers and shady umbrellas. Guests savor fresh seafood at the poolside restaurant, sip cocktails from the bar, and later explore via kayak or windsurfing adventures.
Sparkling blue waters beckon from the outdoor pool, complete with plush sun loungers and shady umbrellas. Guests savor fresh seafood at the poolside restaurant, sip cocktails from the bar, and later explore via kayak or windsurfing adventures.
The price is $124
$124
$172 total
includes taxes & fees
Jun 7 - Jun 8
Southernmost House - Adult Exclusive
Southernmost House - Adult Exclusive4.0 star property
Old Town Key West
- Outdoor pool
- Pool loungers
- Near the beach
9.4 out of 10, Exceptional, (1,001 reviews)
9.4/10
Exceptional
(1,001 reviews)
The price is $191
$191
$342 total
includes taxes & fees
Jun 21 - Jun 22
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Hotels with pools and free breakfast in Key West
9.0 out of 10, Wonderful, (1413)
9.0/10
Wonderful
(1413)
The price is $159
$159
$236 total
includes taxes & fees
Jun 15 - Jun 16
Silver Palms Inn & Historic Homes
Silver Palms Inn & Historic Homes3.5 star property
Old Town Key West
9.4 out of 10, Exceptional, (1039)
9.4/10
Exceptional
(1039)
The price is $112
$112
$193 total
includes taxes & fees
Jun 8 - Jun 9
9.0 out of 10, Wonderful, (1377)
9.0/10
Wonderful
(1377)
The price is $179
$179
$201 total
includes taxes & fees
Jun 7 - Jun 8
Hilton Garden Inn Key West / The Keys Collection
Hilton Garden Inn Key West / The Keys Collection3.5 star property
New Town
8.0 out of 10, Very Good, (1230)
8.0/10
Very Good
(1230)
The price is $115
$115
$157 total
includes taxes & fees
Jun 21 - Jun 22
Authors of Key West Guest House
Authors of Key West Guest House3.0 star property
Key West Historic District
9.2 out of 10, Wonderful, (1007)
9.2/10
Wonderful
(1007)
The price is $119
$119
$134 total
includes taxes & fees
Jun 8 - Jun 9
DoubleTree Resort by Hilton Grand Key - Key West
DoubleTree Resort by Hilton Grand Key - Key West4.0 star property
Key West
8.4 out of 10, Very Good, (1031)
8.4/10
Very Good
(1031)
The price is $147
$147
$199 total
includes taxes & fees
Jun 28 - Jun 29
9.0 out of 10, Wonderful, (1792)
9.0/10
Wonderful
(1792)
The price is $128
$128
$209 total
includes taxes & fees
Jul 5 - Jul 6
The Reach Key West, Curio Collection by Hilton
The Reach Key West, Curio Collection by Hilton4.0 star property
Old Town Key West
8.6 out of 10, Excellent, (1008)
8.6/10
Excellent
(1008)
The price is $187
$187
$278 total
includes taxes & fees
Jul 1 - Jul 2
Fairfield by Marriott Inn & Suites Key West at The Keys Collection
Fairfield by Marriott Inn & Suites Key West at The Keys Collection3.5 star property
New Town
8.6 out of 10, Excellent, (1014)
8.6/10
Excellent
(1014)
The price is $143
$143
$189 total
includes taxes & fees
Jun 10 - Jun 11
Casa Marina Key West, Curio Collection by Hilton
Casa Marina Key West, Curio Collection by Hilton4.0 star property
Old Town Key West
8.4 out of 10, Very Good, (688)
8.4/10
Very Good
(688)
The price is $256
$256
$355 total
includes taxes & fees
Jun 17 - Jun 18
4-star hotels with pools in Key West
9.0 out of 10, Wonderful, (1413)
9.0/10
Wonderful
(1413)
The price is $159
$159
$236 total
includes taxes & fees
Jun 15 - Jun 16
9.4 out of 10, Exceptional, (1272)
9.4/10
Exceptional
(1272)
The price is $151
$151
$230 total
includes taxes & fees
Jul 2 - Jul 3
DoubleTree Resort by Hilton Grand Key - Key West
DoubleTree Resort by Hilton Grand Key - Key West4.0 star property
Key West
8.4 out of 10, Very Good, (1031)
8.4/10
Very Good
(1031)
The price is $147
$147
$199 total
includes taxes & fees
Jun 28 - Jun 29
Casa Marina Key West, Curio Collection by Hilton
Casa Marina Key West, Curio Collection by Hilton4.0 star property
Old Town Key West
8.4 out of 10, Very Good, (688)
8.4/10
Very Good
(688)
The price is $256
$256
$355 total
includes taxes & fees
Jun 17 - Jun 18
The Reach Key West, Curio Collection by Hilton
The Reach Key West, Curio Collection by Hilton4.0 star property
Old Town Key West
8.6 out of 10, Excellent, (1008)
8.6/10
Excellent
(1008)
The price is $187
$187
$278 total
includes taxes & fees
Jul 1 - Jul 2
8.8 out of 10, Excellent, (1813)
8.8/10
Excellent
(1813)
The price is $225
$225
$316 total
includes taxes & fees
Jun 28 - Jun 29
8.4 out of 10, Very Good, (2322)
8.4/10
Very Good
(2322)
The price is $125
$125
$197 total
includes taxes & fees
Jun 7 - Jun 8
Southernmost House - Adult Exclusive
Southernmost House - Adult Exclusive4.0 star property
Old Town Key West
9.4 out of 10, Exceptional, (1001)
9.4/10
Exceptional
(1001)
The price is $191
$191
$342 total
includes taxes & fees
Jun 21 - Jun 22
9.0 out of 10, Wonderful, (1155)
9.0/10
Wonderful
(1155)
The price is $262
$262
$364 total
includes taxes & fees
Jun 10 - Jun 11
Hyatt Centric Key West Resort and Spa
Hyatt Centric Key West Resort and Spa4.0 star property
Key West Historic District
9.0 out of 10, Wonderful, (1003)
9.0/10
Wonderful
(1003)
The price is $220
$220
$317 total
includes taxes & fees
Jun 21 - Jun 22
Hotels with pools and hot tubs in Key West
Hilton Garden Inn Key West / The Keys Collection
Hilton Garden Inn Key West / The Keys Collection3.5 star property
New Town
8.0 out of 10, Very Good, (1230)
8.0/10
Very Good
(1230)
The price is $115
$115
$157 total
includes taxes & fees
Jun 21 - Jun 22
9.0 out of 10, Wonderful, (1792)
9.0/10
Wonderful
(1792)
The price is $128
$128
$209 total
includes taxes & fees
Jul 5 - Jul 6
8.6 out of 10, Excellent, (2269)
8.6/10
Excellent
(2269)
The price is $138
$138
$250 total
includes taxes & fees
Jun 7 - Jun 8
Courtyard by Marriott Key West Waterfront
Courtyard by Marriott Key West Waterfront3.0 star property
Northside Resort
8.8 out of 10, Excellent, (1003)
8.8/10
Excellent
(1003)
The price is $199
$199
$224 total
includes taxes & fees
Jun 14 - Jun 15
The Southernmost Inn - Adults Only
The Southernmost Inn - Adults Only3.0 star property
Old Town Key West
8.4 out of 10, Very Good, (1377)
8.4/10
Very Good
(1377)
The price is $121
$121
$181 total
includes taxes & fees
Jun 10 - Jun 11
8.4 out of 10, Very Good, (2322)
8.4/10
Very Good
(2322)
The price is $125
$125
$197 total
includes taxes & fees
Jun 7 - Jun 8
8.2 out of 10, Very Good, (1012)
8.2/10
Very Good
(1012)
The price is $156
$156
$226 total
includes taxes & fees
Jun 8 - Jun 9
The Cabana Inn Key West - Adults Only
The Cabana Inn Key West - Adults Only3.0 star property
Old Town Key West
9.0 out of 10, Wonderful, (1004)
9.0/10
Wonderful
(1004)
The price is $134
$134
$196 total
includes taxes & fees
Jun 16 - Jun 17
Paradise Inn Key West - Adults Only
Paradise Inn Key West - Adults Only3.5 star property
Old Town Key West
9.2 out of 10, Wonderful, (1003)
9.2/10
Wonderful
(1003)
The price is $152
$152
$216 total
includes taxes & fees
Jun 15 - Jun 16
9.8 out of 10, Exceptional, (1004)
9.8/10
Exceptional
(1004)
The price is $239
$239
$269 total
includes taxes & fees
Jun 9 - Jun 10
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Top neighborhoods in Key West
Old Town Key West
Old Town, the historic heart of Key West, boasts a central business district and numerous tourist attractions. Explore the Key West Aquarium, Ernest Hemingway House, Mallory Square, and more in this vibrant area.
Photo by Ronaldo Esteves
Open Photo by Ronaldo Esteves
New Town
New Town gives you a quieter slice of Key West living away from the tourist crowds. This peaceful residential area offers wide streets for strolling and a glimpse into authentic island life. Nearby Smathers Beach and the Key West Tropical Forest provide natural escapes when you need a break from the bustle. Budget-friendly chain hotels and vacation rentals make this area wallet-friendly for longer stays. Cuban-American eateries and family restaurants offer affordable meals, while shopping plazas with grocery stores help you feel right at home. A car is handy, but free parking is plentiful throughout the neighborhood.
Key West Historic District
Old Town Key West boasts a rich history with 2485 historic buildings, and is home to popular attractions like Ernest Hemingway House and Mallory Square. Enjoy the lively atmosphere in the central business district.
Downtown Key West
Downtown Key West dazzles with its historic charm and non-stop energy. Wander Duval Street's lively scene, visit Hemingway's famous six-toed cat sanctuary, or catch the sunset celebration at Mallory Square where fire-breathers and musicians perform against stunning Gulf backdrops. The neighborhood's Victorian mansions with gingerbread trim and weathered coral stone churches create a unique tropical atmosphere. The area serves up fresh seafood from casual waterfront joints to upscale restaurants. Most attractions sit within a walkable six-block radius, though you can hop on the Conch Tour Train when your feet need a break. Boutique hotels and historic inns with tropical courtyards offer charming places to crash after experiencing the legendary bar scene.
Uptown - Upper Duval
Key West's Uptown - Upper Duval neighborhood has a host of places to visit such as Southernmost Point and Duval Street.
Top landmarks in Key West
Smathers Beach
4.2/5 (8,320 reviews)
Whether you want to collect beach glass or watch the sunset, Smathers Beach is a spot you might want to check out, located 1.7 mi (2.8 km) from central Key West. If you want to continue walking by the waves, head to Clarence S. Higgs Memorial Beach Park located nearby.
Ernest Hemingway Home and Museum
4.6/5 (8,543 reviews)
Ernest Hemingway Home and Museum is just one of the attractions in Old Town Key West, Key West so you might want to stop by during your trip. Why not take a stroll along the beaches and watch the sunset while you're here? If you want to experience more of the culture Key West has to offer, head to Key West Lighthouse and Keeper's Quarters Museum, Duval Street, and Key West Butterfly and Nature Conservatory.
