Which is the best family rental in Truman Annex?

There are many large, family-friendly vacation homes available in Truman Annex; however, here are the most popular family rentals listed on our site:

Can we get self-catering vacation rentals in Truman Annex?

Yes, there are self-catering vacation homes in that have hot tubs, swimming pools, & other amenities.

What are the best luxury vacation rentals near Truman Annex?

There are more than 48 luxury villas and vacation homes in or near Truman Annex. Filter by price to compare find the most expensive places to stay on .

Truman Annex Rentals By Owner

Waterfront Resort, Songwriter’s Fest, Old Town, Sleeps 2, Swimming Pool, Hot Tub

From US $444

New

Resort

Waterfront Resort, Songwriter’s Fest, Old Town, Sleeps 2, Swimming Pool, Hot Tub

Air Conditioner
Pool
TV

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From US $716

|

8.6 (1146 Reviews)

Resort

Opal Key Resort & Marina

Air Conditioner
Parking
Pet Friendly

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Sunset Harbor Resort & Spa, Hot Tub, Pool

From US $1,941

10.0 (1 Review)

Resort

Sunset Harbor Resort & Spa, Hot Tub, Pool

Air Conditioner
Parking
Pool

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𝐅𝐢𝐧𝐝𝐢𝐧𝐠𝐌𝐞𝐢𝐥𝐢 Near Duval Street, Waterfront Sunset Harbor Resort. 2BR

From US $972

New

Resort

𝐅𝐢𝐧𝐝𝐢𝐧𝐠𝐌𝐞𝐢𝐥𝐢 Near Duval Street, Waterfront Sunset Harbor Resort. 2BR

Air Conditioner
Parking
Pool

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Sunset Harbor Resort & Spa, In Town, Marina, Hot Tub.

From US $957

New

Resort

Sunset Harbor Resort & Spa, In Town, Marina, Hot Tub.

Air Conditioner
Parking
Pool

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Hyatt Sunset Harbour Resort-Prime location on Key West!

From US $908

New

Resort

Hyatt Sunset Harbour Resort-Prime location on Key West!

Air Conditioner
Parking
Pool

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Sunset Harbor Resort in Key West-Hemingway Days 2 BR-week of July 19-25, 2026

From US $891

New

Resort

Sunset Harbor Resort in Key West-Hemingway Days 2 BR-week of July 19-25, 2026

Air Conditioner
Security/Safety
Bedding/Linens

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Sunset Harbor Resort, Marina, In Town, Hot Tub, Pool, Balcony

From US $774

New

Resort

Sunset Harbor Resort, Marina, In Town, Hot Tub, Pool, Balcony

Air Conditioner
Parking
Pool

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From US $225

New

Resort

Hyatt Vacation Club in Key West- Studio

Security/Safety
Child Friendly

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NEAR DUVAL ST! Sunset Harbor Oasis + Amenities, 2-Bedroom Suite

From US $700

5.0 (1 Review)

Resort

NEAR DUVAL ST! Sunset Harbor Oasis + Amenities, 2-Bedroom Suite

Air Conditioner
Pool
TV

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Waterfront Retreat, Old Town, Hyatt, 4 Nights, Sleeps 4, Swimming Pool, Hot Tub

From US $550

5.0 (1 Review)

Resort

Waterfront Retreat, Old Town, Hyatt, 4 Nights, Sleeps 4, Swimming Pool, Hot Tub

Air Conditioner
Pool
TV

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WATERFRONT Sunset Harbor Resort in Old Town+ Resort Amenities, 2BR Suite

From US $792

3.5 (2 Reviews)

Resort

WATERFRONT Sunset Harbor Resort in Old Town+ Resort Amenities, 2BR Suite

Air Conditioner
Pool
TV

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Waterfront Retreat, Offshore Races, 3 Nights, Sleeps 6, Pool, Hot Tub, Hyatt

New

From US $1,695

New

Resort

Waterfront Retreat, Offshore Races, 3 Nights, Sleeps 6, Pool, Hot Tub, Hyatt

Air Conditioner
Pool
TV

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Hyatt Sunset Harbor Resort, Pool, Hot Tub!

From US $1,041

New

Resort

Hyatt Sunset Harbor Resort, Pool, Hot Tub!

Air Conditioner
Pool
TV

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1 Hyatt Sunset Harbor Resort, Keys, Pool, Hot Tub

From US $995

New

Resort

1 Hyatt Sunset Harbor Resort, Keys, Pool, Hot Tub

Air Conditioner
Pool
Wheelchair Accessible

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From US $525

New

Resort

Waterfront Retreat, Old Town, Hyatt, 4 Nights, Sleeps 4, Swimming Pool, Hot Tub

Air Conditioner
Pool
TV

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Waterfront Retreat, Fantasy Fest, Old Town, 7 Nights, Sleeps 2, Pool, Hyatt

From US $495

New

Resort

Waterfront Retreat, Fantasy Fest, Old Town, 7 Nights, Sleeps 2, Pool, Hyatt

Air Conditioner
Pool
TV

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Waterfront Retreat, Offshore Races, 7 Nights, Sleeps 2, Pool, Hot Tub, Hyatt

New

From US $490

New

Resort

Waterfront Retreat, Offshore Races, 7 Nights, Sleeps 2, Pool, Hot Tub, Hyatt

Air Conditioner
Pool
TV

View Availability

Waterfront Retreat, Old Town, 3 Nights, Sleeps 4, Hyatt, Swimming Pool, Hot Tub

From US $415

New

Resort

Waterfront Retreat, Old Town, 3 Nights, Sleeps 4, Hyatt, Swimming Pool, Hot Tub

Air Conditioner
Pool
TV

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Waterfront Retreat, Old Town, 7 Nights, Sleeps 2, Hyatt, Swimming Pool, Hot Tub

From US $395

New

Resort

Waterfront Retreat, Old Town, 7 Nights, Sleeps 2, Hyatt, Swimming Pool, Hot Tub

Air Conditioner
Pool
TV

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Waterfront Retreat, Fantasy Fest, Old Town, 7 Nights, Sleeps 2, Pool, Hot Tub

From US $374

New

Resort

Waterfront Retreat, Fantasy Fest, Old Town, 7 Nights, Sleeps 2, Pool, Hot Tub

Air Conditioner
Pool
TV

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1 Bedroom, Hyatt Club Sunset Harbor, Full Kitchen, Acces to Resort , Amenities

From US $204

10.0 (1 Review)

Resort

1 Bedroom, Hyatt Club Sunset Harbor, Full Kitchen, Acces to Resort , Amenities

Air Conditioner
Parking
Pool

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From US $1,127

2.0 (1 Review)

Resort

𝐅𝐢𝐧𝐝𝐢𝐧𝐠𝐌𝐞𝐢𝐥𝐢 Near Duval Street, Waterfront Sunset Harbor Resort. 2BR

Air Conditioner
Parking
Pool

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Waterfront Resort, Songwriter’s Fest, Old Town, Sleeps 6, Swimming Pool, Hot Tub

From US $1,232

New

Resort

Waterfront Resort, Songwriter’s Fest, Old Town, Sleeps 6, Swimming Pool, Hot Tub

Air Conditioner
Pool
TV

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Truman Annex Rentals By Owner

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